Events in Freeport, IL

● Listings verifiedWednesday, September 9 · every listing checked against its source by our Freeport editors

14This week
52Next 30 days
1Free this week
43Venues tracked
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This weekend in Freeport

The ones worth planning around. All 9 weekend events →

Live music in Freeport

6 shows this weeksee the full live-music calendar →

  • Fri 7pm

    Grass Attack/@ Lena Lions Fall Festival

    122 E Main St, Lena · verified Sep 6
    See details

    Grass Attack appears at the Lena Lions Fall Festival with a set grounded in Newgrass, pairing familiar songs on bluegrass instruments with traditional bluegrass numbers. The group often plays festivals, fairs, park concerts, wineries, and breweries across northern Illinois and southern Wisconsin. The lineup features Randy Tackett on guitar and lead vocals, Jeff Wagner on banjo with lead and harmony vocals, Liz Wagner on mandolin with lead and harmony vocals, Rick Nolting on upright and electric bass with harmony vocals, and Laura Lanza on fiddle and other instruments as needed with lead and harmony vocals. The band has two recordings available to stream or purchase.

    Event website ↗
  • Fri 8pm

    KARAOKE AT THE COPPER COW

    4 Carrollton Blvd, Mt Carroll · verified Sep 6
    See details

    Sing your go-to tracks at The Copper Cow during a karaoke night. Pick the songs you want, take the microphone, and perform solo or with friends. Prefer to skip the spotlight? You can chime in from your table while enjoying drinks.

    Event website ↗
  • Sat 5pm

    Freedom on the Rocks

    121 N Harlem Ave, Freeport · verified Sep 6
    See details

    Freedom on the Rocks marks America’s 250th with a red, white, and blue celebration filled with cocktails, live music, and community recognition. The evening features the presentation of the annual Cultural Leadership Awards and the unveiling of the United We Create Mural. Enjoy live music by the Highland Community College Big Band, an all-American cookout with Marketside Meats & Deli, desserts by Bezzie’s Bakery, and a full-service cash bar. Proceeds benefit the Freeport Art Museum’s work to keep admission free and to provide hands-on arts experiences for visitors of all ages each day. The United We Create Mural and related community programs are supported by grants from the Illinois Arts Council and the Foundation for Northwest Illinois.

    Event website ↗
  • Sat 7pm

    The Bacon Brothers LIVE from The Rhythm Section Ampitheater

    The Rhythm Section Amphitheater, 412 S Mill St, Mt Carroll · verified Sep 6
    See details

    RSA & NTL Productions present The Bacon Brothers featuring Kevin Bacon live at The Rhythm Section Ampitheater. Special guests Miles Nielsen & The Rusted Hearts and Myron Elkins are set to perform as part of the lineup.

    Event website ↗

All upcoming events, day by day

Every event we track in Freeport this week, in order. After one kind of thing? Live music has their own calendar.

Wednesday, September 9 0 events
Thursday, September 10 0 events
Friday, September 11 3 events
  • 5pm

    Freeport Martial Arts Community Open Mat

    105 W Main St, Freeport · verified Sep 6
    See details

    Sharpen skills, get extra rounds, and connect with local grapplers at a supportive open mat hosted by Freeport Martial Arts. Practitioners from any academy or affiliation are welcome, and all experience levels can train together in a no-ego environment focused on technical growth and hard work. The session is unstructured with ample space to choose your own focus. Roll Brazilian jiu-jitsu in gi or no-gi, refine submission wrestling with takedowns, cage work, and fast scrambles, or use the designated area for MMA sparring, where 16 oz gloves and shin guards are required for live work. Drilling with a partner is encouraged if you prefer skill refinement over live rounds. Safety and cleanliness guide the mat culture. Honor taps promptly, arrive with clean gear and uniforms, and participate whether you are a hobbyist or an active competitor. Bring your own equipment such as mouthguards and wraps, and pack water. Hydration stations are available on site.

    Event website ↗
  • 7pm

    Grass Attack/@ Lena Lions Fall Festival

    122 E Main St, Lena · verified Sep 6
    See details

    Grass Attack appears at the Lena Lions Fall Festival with a set grounded in Newgrass, pairing familiar songs on bluegrass instruments with traditional bluegrass numbers. The group often plays festivals, fairs, park concerts, wineries, and breweries across northern Illinois and southern Wisconsin. The lineup features Randy Tackett on guitar and lead vocals, Jeff Wagner on banjo with lead and harmony vocals, Liz Wagner on mandolin with lead and harmony vocals, Rick Nolting on upright and electric bass with harmony vocals, and Laura Lanza on fiddle and other instruments as needed with lead and harmony vocals. The band has two recordings available to stream or purchase.

    Event website ↗
  • 8pm

    KARAOKE AT THE COPPER COW

    4 Carrollton Blvd, Mt Carroll · verified Sep 6
    See details

    Sing your go-to tracks at The Copper Cow during a karaoke night. Pick the songs you want, take the microphone, and perform solo or with friends. Prefer to skip the spotlight? You can chime in from your table while enjoying drinks.

    Event website ↗
Saturday, September 12 8 events
  • 8am

    Friends Forever Car Show

    966 Rudy Rd, Freeport · verified Sep 6
    Free

    A family-friendly car show and open house honors Bruce Nielsen while supporting Friends Forever Humane Society and the animals in its care. Spectators receive free entry and can enjoy music, food, raffles, and door prizes while exploring an array of vehicles competing for Top 40 awards, including Best of Show. Held rain or shine at Friends Forever Humane Society, all proceeds benefit FFHS and its mission to help shelter animals.

    Event website ↗
  • 8am

    Tee Off on Crime

    The Freeport Club, 1614 South Park Boulevard, Freeport · verified Sep 6
    See details

    Tee Off on Crime 2026 is a golf outing featuring the Sponsor a Cop option, a Bloody Mary bar, the Gahm Enterprises golf ball launcher, crime scene themed bunkers, and offerings from the Wood Pellet Pizza Oven Company. Entry is $125 and includes 18 holes with a cart, access to the Bloody Mary bar, pizza samples and other treats, lunch, and plenty of on-course fun. Those who are not playing can still participate by becoming a sponsor or by sponsoring a cop to enjoy a day on the course.

    Event website ↗
  • 8am

    Safe Sitter

    1307 2nd St, Monroe · verified Sep 6
    See details

    Safe Sitter is a single day class for students in grades 6 through 8 who want to be prepared when staying home alone, caring for younger siblings, or babysitting. Participants learn how to respond to choking and practice CPR and choking rescue with mannequins. The course also covers what to do during severe weather and reinforces skills through activities and role playing. This program is presented in partnership with SSM Health Monroe Hospital and Clinics. Registration is required. The cost is $60 for members and $80 for non-members. Sign up online or at the YMCA.

    Event website ↗
  • 8am

    Diesel Drags & Truck Show

    7344 N River Rd, Byron · verified Sep 6
    See details

    Test your truck’s speed and style in a competitive showcase. Awards will be given to the three quickest Cummins, three quickest Duramax, and three quickest Power Stroke, plus the fastest manual transmission, best appearing, and most unique. Truck show entry is included with any paid admission.

    Event website ↗
  • 9:30am

    Tarot & Oracle Readings with Courtney

    Rootz & Branchez, 101 W. Main St., Freeport · verified Sep 6
    See details

    Courtney is offering tarot and oracle sessions at Rootz & Branchez, with appointments available in person or virtually. Choose a three-card draw up to 10 minutes for $11, a five-card draw up to 20 minutes for $22, or a full reading up to 30 minutes for $33. A one-hour tarot reading with oracle insights is available for $60. When booking, include your preferred time and the package you want. Sign-ups are accepted by email at rootzandbranchez@gmail.com, by leaving a message at 815-616-5422, through Messenger, or by stopping into the shop.

    Event website ↗
  • 3pm

    Ladies Banquet at Bethany

    16529 W Church Rd, Brodhead · verified Sep 6
    See details

    Bethany Lutheran Church hosts the third annual Ladies Banquet, welcoming women of every age for an uplifting gathering. The program carries through the afternoon into the evening with conversation, encouragement, and a shared meal. It is planned as a time to renew hearts and spirits in a warm, supportive atmosphere. Friends are welcome.

    Event website ↗
  • 5pm

    Freedom on the Rocks

    121 N Harlem Ave, Freeport · verified Sep 6
    See details

    Freedom on the Rocks marks America’s 250th with a red, white, and blue celebration filled with cocktails, live music, and community recognition. The evening features the presentation of the annual Cultural Leadership Awards and the unveiling of the United We Create Mural. Enjoy live music by the Highland Community College Big Band, an all-American cookout with Marketside Meats & Deli, desserts by Bezzie’s Bakery, and a full-service cash bar. Proceeds benefit the Freeport Art Museum’s work to keep admission free and to provide hands-on arts experiences for visitors of all ages each day. The United We Create Mural and related community programs are supported by grants from the Illinois Arts Council and the Foundation for Northwest Illinois.

    Event website ↗
  • 7pm

    The Bacon Brothers LIVE from The Rhythm Section Ampitheater

    The Rhythm Section Amphitheater, 412 S Mill St, Mt Carroll · verified Sep 6
    See details

    RSA & NTL Productions present The Bacon Brothers featuring Kevin Bacon live at The Rhythm Section Ampitheater. Special guests Miles Nielsen & The Rusted Hearts and Myron Elkins are set to perform as part of the lineup.

    Event website ↗
Sunday, September 13 1 event
  • 1pm

    Dance with Second Time Around Band

    1217 17th Ave, Monroe · verified Sep 6
    See details

    Enjoy dancing with the Second Time Around Band in Monroe, Wisconsin. Entry costs $12, and seating is unassigned.

    Event website ↗
Monday, September 14 0 events
Tuesday, September 15 2 events
  • 5:30pm

    Grief Support Group

    N3152 State Rd 81, Monroe, WI, United States, Wisconsin 53566, Monroe · verified Sep 6
    See details

    A Time to Talk is a grief support group offering a caring place for anyone coping with the loss of a loved one. Participants can share their stories, express difficult emotions, or simply listen in a respectful setting among people who understand. The group emphasizes a sense of community, practical tools for coping, and encouragement to continue healing while honoring those who have passed. Meetings take place at the Green County Human Services Building in the lower level, Multipurpose Rooms 2 and 3. This group is not held at the ADRC. The location may change, and any cancellations will be announced on the ADRC Facebook page.

    Event website ↗
  • 6pm

    Squeezebox Night

    Ratskeller Restaurant, 1217 17th Ave, Monroe · verified Sep 6
    See details

    Accordion and button box enthusiasts gather at Turner Hall's Ratskeller Restaurant for a relaxed open jam. Musicians who play other instruments are welcome to take part. The restaurant features a themed Squeezebox Night menu for diners who want to enjoy live music with their meal.

    Event website ↗

All upcoming events67 more events through Dec 1

Everything else on Freeport's calendar over the next 30 days, in order.

Wednesday, September 16 1 event
  • 1pm

    Diabetes 101: Heart Healthy Eating

    Senior Resource Center, 206 E Stephenson St, Freeport · verified Sep 6
    See details

    This Heart Healthy Eating session is part of Diabetes 101, a four week educational series presented by University of Illinois Extension in collaboration with the Senior Resource Center for people living with diabetes, those newly diagnosed, and supporters. The class highlights heart smart nutrition within diabetes management and is offered alongside sessions on meal planning, physical activity, weight and stress management, and partnering with a healthcare team to support health and quality of life. Participants may register for the entire series or select individual sessions. The fee is $5 per session and includes educational materials, and advance registration is requested.

    Event website ↗
Thursday, September 17 4 events
  • 1pm

    2026 Heartland Hangout Handpan Gathering

    Stronghold Castle & Retreat Camp, 1923 IL-2, Oregon · verified Sep 8
    See details

    Set against the backdrop of Stronghold Castle Retreat Center in Oregon, Illinois, this handpan gathering blends castle, camping and river vibes with time devoted to music, learning and connection. Now in its third year at this venue, it features performances and sessions with Mar Loi, Amy Naylor, Mumi and Dan Mulqueen, plus workshops, lessons, open mic opportunities and a calming Zen Den focused on sound healing. New and used handpans will be available for purchase. Open to beginners, intermediate players and seasoned handpan musicians, the experience is welcoming to everyone. Tickets include festival admission, concerts, workshops, open mic participation, group activities, lodging, meals and access to purchase raffle tickets for additional items.

    Event website ↗
  • 1:30pm

    IFA 21st Annual Conference

    Jarrett Prairie Center, 7993 N River Rd, Byron · verified Sep 6
    See details

    The Illinois Forestry Association’s 21st annual conference at the Jarrett Prairie Center brings together forest landowners, natural resource professionals, students, and conservation advocates for three days focused on Illinois forestry, wildlife, and habitat stewardship. The program includes expert presentations on restoring oak ecosystems, creating habitat for forest birds, the use of drones for herbicide applications, and incentives available to landowners. Participants can also take part in hands-on workshops in ethnobotany, foraging, and seed propagation, explore the Nachusa Grasslands on guided field tours, connect at a Women Owning Woodlands coffee meet-up, and take part in a silent auction and a social hour. Registration offers an early-bird price of $50, general admission at $65, and a student rate of $35, with attendance capped at 70 people.

    Event website ↗
  • 5pm

    Cheese Days Community Night

    Downtown Historic Courthouse Square, 1016 16th Ave, Monroe · verified Sep 8
    See details

    Live music from the Rhythm Kings sets the tone. The Cheese Days beer stand will be open, and many food vendors will be serving.

    Event website ↗
  • 5pm

    Main Street Monroe Concert on the Square

    Green County Courthouse, 1016 16th Ave, Monroe · verified Sep 6
    See details

    Celebrate the finale of the 2026 concerts on the square with a community night in partnership with Green County Cheese Days. A leading Milwaukee dance band keeps the energy high with a big, crowd-moving sound that closes the summer block party and kicks off Cheese Days weekend. Music takes place on the Martha Bernet Stage on the south side of the square. The summer concert series is supported by the Colony Brands Foundation, and intermission is made possible by the John and Katie Baumann Inspiration Project.

    Event website ↗
Friday, September 18 5 events
  • 3pm

    The Decade Rocks the Main Stage

    Cheese Days Festival, 1016 16th Ave, Monroe · verified Sep 6
    See details

    Cheese Days returns to Monroe in this even-year tradition, and The Decade is back after drawing a big crowd under the Hospitality Tent in 2024. This time the band steps onto the Main Stage at the Cheese Days Festival and teams up again with Tower Sound. The set spotlights big hits from the 70s and 80s rock era by Def Leppard, Journey, AC/DC, Van Halen, Ozzy Osbourne, Bon Jovi, Joan Jett, Poison, Pat Benatar, Ratt, Mötley Crüe, Billy Squier, Kiss, Loverboy, Foreigner, Metallica, Billy Idol, Twisted Sister, Styx, John Mellencamp, Autograph, Tom Petty, Rick Springfield, The Romantics, Duran Duran, The Clash, Bryan Adams, Violent Femmes, Blondie, Tommy Tutone, Kenny Loggins, and more. The performance also marks the band’s seventh year together and showcases The Decade’s 80s rock experience.

    Event website ↗
  • 6:45pm

    The Mascot Theory

    Cheese Days Festival, 1016 16th Ave, Monroe · verified Sep 6
    See details

    The Mascot Theory returns to Cheese Days with a performance in the Hospitality Tent at the Cheese Days Festival.

    Event website ↗
  • 7pm

    Alphorns

    Historic Green County Courthouse, 1016 16th Ave, Monroe · verified Sep 6
    See details

    A staple of Cheese Days, the Alphorns help set the celebration's atmosphere.

    Event website ↗
  • 8pm

    Hanks Polka Boys

    Cactus Co. Booze N’ Bites, 1610 11th St., Monroe · verified Sep 6
    See details

    Hank’s Polka Boys lead a heartfelt tribute to Henry Blumer with an evening of traditional polka at Cactus Co. Booze & Bites. The program highlights the classic rhythms and familiar melodies he loved, celebrating the community spirit and dance floor camaraderie he inspired among musicians, friends, and family. In keeping with polka tradition, the gathering welcomes friends and relatives who wish to bring instruments and play alongside Jason and Adam, whether on accordion, concertina, drums, brass, or by clapping in time. Expect simple, sincere polka performed in the tradition that shaped generations and continues to bring people together.

    Event website ↗
  • 9pm

    Bombargo

    Martha Bernet Main Stage, 1016 16th Ave, Monroe · verified Sep 6
    See details

    Bombargo takes the stage at Cheese Days in Monroe, celebrating the release of the new single "How Will I Ever Fall In Love Again." The performance highlights the track and brings a groove-filled vibe that keeps the crowd moving.

    Event website ↗
Saturday, September 19 8 events
  • 8am

    Cheese Days Saturday

    Downtown Historic Courthouse Square, 1016 16th Ave, Monroe · verified Sep 6
    See details

    Festivities include music, food, and beer, along with alphorn performances and yodelers. Highlights feature the Cheese Days Chase, the Cheese Tent, the Family Farm Adventure Tent, and a Tractor Show, with more to discover. The headliner is Boogie and the YoYoz.

    Event website ↗
  • 8am

    Tiger 10 Miler

    Byron Forest Preserve, 3998 E Whitaker Rd, Byron · verified Sep 6
    See details

    This 10 mile race takes place at Byron Forest Preserve. Packet pickup is available at the Byron Park District Guest Service Desk, and check-in is offered on race morning before the start. The entry fee is $80 per person.

    Event website ↗
  • 9am

    Morning Puzzle Meet-Up

    Brodhead Memorial Public Library, Brodhead · verified Sep 6
    See details

    Puzzle enthusiasts gather for a relaxed meet-up with plenty of solving, treats, and conversation. Bring a favorite puzzle to share, or choose one from the available collection and enjoy working alongside others.

    Event website ↗
  • 9:30am

    Tarot with Kennia

    Rootz & Branchez, 101 W Main St, Freeport · verified Sep 6
    See details

    Tarot sessions with Kennia are available at Rootz & Branchez. Choose from a three card draw lasting up to ten minutes for $11, a five card draw up to twenty minutes for $22, a full reading up to thirty minutes for $33, or a one hour session for $60. To reserve a spot, email rootzandbranchez@gmail.com with TAROT in the subject line, call 815-616-5422 and leave a message, send a direct message on Messenger, or stop by the shop. When you reach out, include your preferred time and the package you would like.

    Event website ↗
  • 9:30am

    2nd Annual DIRTY DEEDS Memorial FUN Run

    Freeport, IL · verified Sep 6
    See details

    The second annual Dirty Deeds memorial fun run honors Joe “Dirty” Roth and benefits the Joseph J. Roth Foundation, Inc., helping fund therapy and psychiatric services for children who have lost a parent or guardian. The day centers on a group ride focused on camaraderie and giving back. Registration takes place at 2nd Chance Tavern, where participants can enjoy complimentary biscuits and gravy along with a mimosa special. The route spans about 100 miles with six total stops, beginning at 2nd Chance Tavern and concluding at Wayside Tavern, where dinner is provided for registered participants. Remaining stops will be announced closer to the event. Raffles and prizes include a 50/50 drawing, gift basket raffles, a smart WiFi grill raffle, and a handgun raffle, plus a cash prize for the fun run winner. Tickets for the handgun and grill raffles are limited and may sell out ahead of time. New this year, the traditional poker run gets a twist. Instead of collecting playing cards, participants pick up a special item at each stop, and those who gather all required items qualify for a cash grand prize. Motorcycles, classic cars, and any favorite set of wheels are welcome.

    Event website ↗
  • 12:15pm

    David Austin Band

    Monroe - Downtown Historic Courthouse Square, 1016 16th Ave, Monroe · verified Sep 6
    See details

    The David Austin Band performs at Cheese Days with a squeezebox in the lineup, adding that unmistakable sound to the show.

    Event website ↗
  • 1:30pm

    Northwest Illinois Airshow 2026

    Albertus Airport, 1255 Airport Rd, Freeport · verified Sep 6
    See details

    Celebrating its fifth year, this airshow introduces new performers and features aircraft parked for close-up viewing. Families can enjoy an expanded kids area that includes a parachute ride. A food court with many vendors offers a wide range of choices. The event takes place at Freeport’s Albertus Airport. Advance tickets are $15, admission at the gate is $20, and children 10 and under get in free. On-site parking is available for $5 per vehicle.

    Event website ↗
  • 8:45pm

    Boogie

    Martha Bernet Main Stage, 1016 16th Ave, Monroe · verified Sep 6
    See details

    Returning due to popular demand, Boogie and the Yo-Yoz are back at Cheese Days. A photo was borrowed from their Facebook page, dated September 2024.

    Event website ↗
Sunday, September 20 4 events
  • 10am

    Cheese Days Sunday

    Downtown Historic Courthouse Square, 1016 16th Ave, Monroe · verified Sep 6
    Free

    The event features live music, food, and beer, along with performances showcasing alphorns and yodeling. Visitors can stop by the Cheese Tent and the Family Farm Adventure Tent, with more activities to explore. The Swiss Colony Cheese Days Parade is a featured highlight.

    Event website ↗
  • 12:30pm

    The Swiss Colony Cheese Days Parade

    Historic Green County Courthouse, 1016 16th Ave, Monroe · verified Sep 6
    Free

    This event starts at the Green County Fairgrounds and makes its way to the downtown Square.

    Event website ↗
  • 3pm

    Ctrl Alt Dlt

    Cactus Co. Booze N’ Bites, 1610 11th St., Monroe · verified Sep 6
    See details

    Keep the Cheese Days weekend going with Ctrl Alt Dlt at Cactus Co. Booze N’ Bites. Mark the close of the festivities with a final hoorah before the weekend wraps up. Start time is subject to change.

    Event website ↗
  • 4pm

    New Glarus Yodel Club and Mannerchor

    Downtown Historic Courthouse Square, 1016 16th Ave, Monroe · verified Sep 8
    See details

    This event highlights a longstanding tradition from New Glarus.

    Event website ↗
Thursday, September 24 1 event
  • 10:30am

    Caregiver Support Group

    Monroe · verified Sep 8
    See details

    Caring for a loved one can be both fulfilling and challenging, and this caregiver support group provides a safe, welcoming place to connect with others who understand. Participants can share experiences, discuss obstacles, and learn practical coping strategies and helpful resources, with encouragement offered through every stage of caregiving. Meetings take place at the Green County Human Services Building, Lower Level Multipurpose Room 1. This group does not meet at the ADRC, and the location may change. If a session is cancelled, notice is shared on the ADRC Facebook page. For questions, call the ADRC at 608-328-9499.

    Event website ↗
Friday, September 25 2 events
  • 9am

    Open Sew

    Jane Addams Community Center, 430 W Washington Street, Freeport · verified Sep 6
    See details

    Open Sew at Jane Addams Community Center offers dedicated time to make progress on your projects while sewing alongside others. Assistance is available for any Quiltworx project you are working on, and support is also offered if you want to begin a Quiltworx project. The class fee is $15 per day. Contact the organizer to RSVP. Each day features a potluck lunch, or you may bring your own meal.

    Event website ↗
  • 5pm

    Opening Reception - The Third Space

    Freeport Art Museum, 121 N Harlem Ave, Freeport · verified Sep 6
    See details

    A solo exhibition at the Freeport Art Museum features Shirley Guay and her ongoing exploration of the third space, a method that gives positive and negative space equal importance. Between two positive images lies the area known as the third space, which becomes a central element in her compositions. This approach can be seen in her earlier pieces and continues through her most recent work.

    Event website ↗
Saturday, September 26 1 event
  • 9am

    TCCS Eagle Classic

    Park Hills Golf Course, 3240 W Stephenson St, Freeport · verified Sep 6
    See details

    The TCCS Eagle Classic is a golf event built around camaraderie and purpose, raising support for Tri-County Christian School. It offers a friendly day on the course that benefits students and helps sustain education grounded in Christian faith for future generations. The occasion brings together golfers, sponsors, and supporters united by this mission. Further event details, registration information, and sponsorship opportunities will be shared soon.

    Event website ↗
Sunday, September 27 2 events
  • 1pm

    Dance with the Zweifel Brothers Band

    Turner Hall of Monroe, 1217 17th Ave, Monroe · verified Sep 6
    See details

    General admission is $12. Pricing is higher on Old Year's Night, also known as New Year's Eve. Seating is unassigned and first come, first served.

    Event website ↗
  • 3pm

    Ukulele Express 815

    PJ's Corner Bar, 504 N Stanton St, Davis · verified Sep 6
    See details

    Ukulele Express 815 brings live music to PJ’s Corner Bar for an afternoon session filled with chilled drinks, friendly company, and a lively bar atmosphere.

    Event website ↗
Friday, October 2 2 events
  • 1pm

    Artist Workshop with Woody Olsen: Painting in Abstract

    Freeport Art Museum, 121 N Harlem Ave, Freeport · verified Sep 6
    See details

    Explore abstraction in watercolor during a hands-on workshop with artist Woody Olsen. Through guided exercises, you will layer color and combine watercolor with other media to build depth and create inventive compositions. Emphasis is placed on abstract and imagist approaches, encouraging play, intuition, and a strong personal voice. It suits artists hoping to loosen their process or venture into something different, offering a renewed way to work with watercolor. The fee is $60, or $54 for FAM members, and it includes instruction and all materials.

    Event website ↗
  • 3pm

    COMMUNITY GATHERING WEEKEND AT THE CABIN!! (10 YEARS!!)

    Oregon, Illinois, Oregon · verified Sep 6
    See details

    Mark a decade of connection with a community weekend at the cabin featuring shared meals, wellness sessions, and time outdoors. Choose how to participate: camp with your own tent and gear for $200 per person, reserve a cabin sleeping space for $250 per person, or opt for a Saturday day pass for $85. Everyone brings their own food and drinks to contribute to communal meals. The weekend begins with arrivals, setup, dinner, and an opening circle by the bonfire. Saturday offers a full slate of experiences, including Kundalini yoga with the gong, oracle card manifesting paired with Reiki, an intention craft session, a healing circle, and a triple sound healing, followed by dinner, giveaways, and time around the fire. Sunday features breakfast, meditation, a closing circle, and time to relax and pack up. Highlights include yoga, sound healing, crystals, ceremony, music, crafts, dancing, kayaking, and a raffle, along with friends, fun, and surprises. Children are welcome with supervision, and family rates are available. Bring everything needed for camping if applicable, along with your own food and beverages for shared meals. Reservations are secured with payment.

    Event website ↗
Saturday, October 3 6 events
  • 9am

    Olde English Faire 2026

    Stronghold Camp & Retreat Center, 1923 N IL Route 2, Oregon · verified Sep 6
    See details

    Attendees can experience Renaissance-themed performances, cosplay, and historical reenactments, browse artisan vendors, sample fare from a food court and food trucks, and relax in a royal-themed beer garden. The Castle will be open to visitors, with additional activities taking place across the grounds during this Annual Olde English Faire Fundraiser at Stronghold Camp & Retreat Center in Oregon, Illinois.

    Event website ↗
  • 9am

    Flea Market / Craft Fair

    Leisure Lanes Monroe, 2308 6th Ave, Monroe · verified Sep 6
    Free

    A flea market and craft fair will take place in the Leisure Lanes parking lot, featuring a mix of vendors and handmade goods. Vendor spaces are approximately 16 by 16 feet, and the rental fee is $25, with proceeds donated to a nonprofit organization that will be selected later. Admission and parking are free. To secure a space, a completed registration form and prepayment are required. If weather forces a cancellation, a make-up day is planned for the following Saturday, and if that is also cancelled, payments will be refunded. For details or to register, contact Dee Goepfert at 608-558-0457, email dandee94@charter.net, or stop by Leisure Lanes to pick up a sign-up form.

    Event website ↗
  • 9:30am

    Psychic or Palm Readings with Medium Frankie B.

    Rootz & Branchez, 101 W. Main St., Freeport · verified Sep 6
    See details

    Medium Frankie B. offers private psychic and palm reading sessions at Rootz & Branchez. Psychic readings can include guidance for current decisions and the path ahead, messages from those who have passed, and perspectives on previous lifetimes. Palm readings delve into personal strengths, life lessons, relationships, and direction. Psychic sessions are $99 for 30 minutes or $150 for one hour. Palm readings are $11 for 10 minutes, $22 for 20 minutes, $33 for 30 minutes, or $60 for one hour. Sessions are available by appointment only.

    Event website ↗
  • 10am

    The Dragon's Hoard

    Stronghold Camp & Retreat Center, 1922 N IL Route 2, Oregon · verified Sep 6
    See details

    Experience a festive Olde English faire at Stronghold Camp and Retreat Center, featuring live performances, dancing, jesters, royalty, Vikings, horses, and castle tours. Explore artisan vendors offering handmade wares and enjoy a variety of food trucks between the action. Admission is $10 per person, $5 for children under 12, and free for children under 5.

    Event website ↗
  • 2pm

    Andrew Carnegie's Gospel of Wealth

    Warren Township Public Library, 210 Burnett Ave, Warren · verified Sep 6
    See details

    Explore Andrew Carnegie’s journey from leading the late 19th century steel boom to becoming one of the wealthiest Americans. After retiring in 1901, he turned to philanthropy guided by the Gospel of Wealth, the belief that those with great fortunes have a responsibility to support society. Learn how his commitment to education and world peace contributed to the founding of public libraries.

    Event website ↗
  • 7pm

    Midnight Angel

    Leisure Lanes Monroe, 2308 6th Ave, Monroe · verified Sep 6
    Free

    Midnight Angel kicks off the indoor band season at Leisure Lanes Monroe. The band returns to Monroe with a lineup that includes a couple of fellow Cheesemakers. Admission is free.

    Event website ↗
Sunday, October 4 1 event
  • 8am

    World Power Wheelstanding Championships

    Byron Dragway, 7344 N River Rd, Byron · verified Sep 6
    See details

    A thrilling show on wheels brings gravity-defying action to Byron Dragway. Additional details and updates will be shared as they are announced.

    Event website ↗
Monday, October 5 1 event
  • 5pm

    Relay For Life Spaghetti Dinner and Relay Event

    Koning Maple Lane Event Center, Monroe · verified Sep 6
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    Relay For Life of Green County presents a spaghetti dinner fundraiser and relay event at Koning Maple Lane Event Center. The evening features displays, pick-up of Facebook auction items, and opportunities to sign up for the silent auction and basket drawings. A spaghetti dinner follows, then a program led by the Event Leadership Team, and a Luminaria Ceremony with survivor recognition. Spaghetti dinner tickets are $15, and carry-outs are available. The meal includes spaghetti with meatballs, garlic toast, salad, milk or coffee, and a sweet treat such as brownies, bars, or cookies. Tickets must be secured in advance, and only a very limited number will be available at the event because food is prepared based on expected attendance. Cancer survivors receive a complimentary dinner ticket when they register through ACS and contact Evelyn Crooks. Survivors can register through ACS by calling 1-800-227-2345 or by using a paper form. For more information and to be recognized during the event, contact Evelyn at 608-558-8062 or raisinlady69@gmail.com.

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Friday, October 9 2 events
  • 6pm

    Grass Attack @ The Coliseum Museum of Art, Antiques & Americana

    Coliseum Museum of Art, Antiques & Americana, 124 N 4th St, Oregon · verified Sep 8
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    Grass Attack brings its bluegrass-driven sound to The Coliseum Museum of Art, Antiques & Americana, blending Newgrass with a selection of traditional tunes. The performance centers on familiar songs played on bluegrass instruments while also incorporating classic bluegrass numbers. The band is a frequent presence at festivals and fairs, concerts in community parks, and at breweries and wineries across Iowa, Southern Wisconsin, and Northern Illinois. The lineup features Randy Tackett on guitar with lead vocals, Jeff Wagner on banjo contributing lead and harmony vocals, Liz Wagner on mandolin with lead and harmony vocals, Rick Nolting on upright and electric bass with harmony vocals, and Laura Lanza on fiddle and additional instruments as needed, also sharing lead and harmony vocals. They have two recordings available to stream or purchase.

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  • 6pm

    Moments in Monochrome Awards Reception

    Coliseum Museum of Art, Antiques & Americana, 124 N 4th St, Oregon · verified Sep 6
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    Celebrate Moments in Monochrome at an awards reception featuring judge Heather Shore and music by Grass Attack.

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Saturday, October 10 2 events
  • 9am

    EIE Pickleball Tournament

    Northeast Park, 2708 4th St, Monroe · verified Sep 6
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    Monroe Excellence in Education presents a day of pickleball at Northeast Park that blends friendly competition with community support. The event includes two ways to play, a co-ed tournament and a family tournament, and teams may choose one or participate in both. Registration is $50 per team. It supports education in the community while offering a fun day on the courts.

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  • 7pm

    Think Floyd USA

    Timber Lake Playhouse, 8215 Black Oak Rd, Mount Carroll · verified Sep 6
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    Think Floyd USA brings Pink Floyd’s celebrated catalog to Timber Lake Playhouse in an intimate, seated concert that emphasizes precision, atmosphere, and emotion. Expect soaring guitar lines, rich sonic layers, and an immersive sound that envelops the room. Classic songs from across the band’s eras are presented with a high-quality theater production that feels close and personal. Settle in and let the music carry the night for a captivating live experience from start to finish.

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Sunday, October 11 2 events
  • 10am

    Ogle County Farm Stroll

    Various Ogle County Farms, 2233 S County Farm Rd, Oregon · verified Sep 6
    Free

    Explore Ogle County at the Ogle County Farm Stroll, a self-guided tour of ten family farms where you choose your own route. Visit one stop or all ten to meet local producers, learn how your food is grown, and see what each farm has to offer. The event takes place in any weather. Admission is free, and bringing cash is recommended for purchasing farm goodies. Dress for the conditions and wear closed-toe shoes. Pick up a passport at your first farm, follow the instructions, then drop it off at your final stop to enter a drawing for a prize from a participating farm. You do not need to visit every location to take part, but be sure to include your contact information. A brochure is available. New this year, posted signs will include QR codes for Google Maps directions. For reasonable accommodations, call the Ogle County Extension office at 815-732-2191. Hosted by the Ogle County Master Gardeners, with printing support from Compeer Financial and Stillman Bank.

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  • 1pm

    Dance with Back 40 Band

    Turner Hall of Monroe, 1217 17th Ave, Monroe · verified Sep 6
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    Enjoy a lively social dance with Back 40 Band providing the music. Admission is $12. Seating is not reserved, so choose any open spot and get ready to dance.

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Tuesday, October 13 2 events
  • 2pm

    Fur Real Companionship | Lessons at the Library

    Byron Public Library District, 100 S Washington St, Byron · verified Sep 6
    Free

    Learn how animal companionship can support the well being of older adults in this free workshop. Explore research on how pets can ease loneliness, provide purpose, and encourage activity, plus discover creative alternatives for those who cannot care for a pet. Older adults, family members, and caregivers will find practical guidance for building meaningful connections. A portion of the session includes a webinar with timeless insights and actionable tips for living a healthy, inspired, and fulfilling life at any age. Hosted by the Byron Public Library District. To reserve a spot, call 815-234-5107. For questions or to request a reasonable accommodation, contact Jan at 815-544-3710.

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  • 3pm

    Brodhead Food Truck Nights

    Putnam Park, 520 W 3rd Ave, Brodhead · verified Sep 6
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    Brodhead Food Truck Nights returns to Putnam Park with street-side kitchens serving a mix of savory dishes and a friendly, social vibe. Supported by the Brodhead Chamber of Commerce to celebrate local members and bring neighbors together, this Food Truck Tuesday gathering features multiple trucks and plenty of opportunities to connect with friends. Admission is free, and everyone is welcome.

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Saturday, October 17 4 events
  • 6am

    Girls Gone Rx Illinois

    Kinetic Grit CrossFit, 703 N Walnut St, Byron · verified Sep 6
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    Marking 14 years of strength, sweat, and sisterhood, this all-female team competition brings three-woman squads together for four workouts that value camaraderie as much as results. The atmosphere centers on encouragement and empowerment, creating an energetic day of tough WODs, new personal records, and plenty of cheers. The event supports Compete for a Cure, a breast cancer charity. Each team can create a fundraising page, and those efforts count toward the overall score so performance includes both fitness and philanthropy. Two divisions are offered. The RX division is for seasoned athletes who complete workouts as written, are proficient with pull-ups, double unders, and handstand push-ups, feel confident with a barbell, and can execute full squat snatches or full squat cleans at or above 95 pounds. The BAM, or Badass In the Making, division suits competitors newer to functional fitness or to the competition floor, provides scaling and modifications in most workouts, and emphasizes a supportive, confidence-building experience. Teams receive a unique referral link after registration, and if four teams sign up using that link, their entry is free.

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  • 9am

    Autumn Fest/Día De Los Muertos

    1108 1st Center Ave, Brodhead · verified Sep 6
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    Celebrate the season at Autumn Fest/Día De Los Muertos with a chili cook-off, music, a costume contest, vendors, and more. Look for additional details as the event approaches.

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  • 10am

    2026 Fall Fest

    9995 N Girl Scout Rd, Stillman Valley · verified Sep 6
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    Fall Fest at Camp McCormick offers a full day of family-friendly experiences with community partners hosting program and information stations. Highlights include s’mores by the campfire, time to unwind in the hammock wheel, a scavenger hike, and a walk through the corn maze with opportunities to spot hidden camp gnomes and pick up treats. GSNI’s mobile retail store will be on-site, and food trucks will offer hot lunch options, with sack lunches also welcome. Those working on the America 250 badge set can take part in hands-on activities and crafts that count toward GSUSA patches. The celebration of America’s 250th Birthday features special activity stations, snacks, and the Girl Scout Flag Ceremony tradition. All currently registered Girl Scouts who attend will receive a free Fall Fest Patch and an America 250-themed bar. Troops that attend must maintain proper child-to-adult ratios, and families are welcome. Registration is required for all attendees, and anyone interacting with animals or participating in facilitated activities must submit a signed safety waiver before the event start date.

    Event website ↗
  • 4pm

    L. A. Drive Live @ The Wayside Saloon

    Wayside Saloon, 1802 Crossroads Lane North, Freeport · verified Sep 6
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    Enjoy delicious food in a lively setting with music to match the fun atmosphere.

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Saturday, October 31 1 event
  • 8pm

    Halloween Show at Kings Bar and Grill with The Real Deal at 8pm 1805 S West Av, Freeport, IL

    Kings Bar & Grill, 1805 S West Ave, Freeport · verified Sep 6
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    Kings Bar & Grill hosts a Halloween show featuring The Real Deal, an R&B band known for soulful vocals and high-energy live sets. Drawing from gospel, rhythm and blues, and rock, the group blends power and finesse into a vibrant sound with a genuine, hard-hitting edge. Attendees are encouraged to wear standout Halloween costumes for a lively night of music and fun.

    Event website ↗
Sunday, November 1 1 event
  • 4pm

    Superhero Supper @ Stockton Park House

    600 N Pearl St, Stockton · verified Sep 6
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    Kids can enjoy a superhero themed event at the Stockton Park House with games, superhero visits, photo opportunities and more. Participation is limited to the first 25 kids and the cost is $25 per child. Costumes are encouraged, so dress as a favorite hero or villain. Advance sign up and prepayment are required. To register, call or text Michelle at 815-541-3473, Darcie at 815-275-0300, or Lizzy at 815-990-1364.

    Event website ↗
Tuesday, November 3 1 event
  • 6pm

    Tour of Hearts Charity Raffle @Leisure Lanes

    Leisure Lanes Monroe, 2308 6th Ave, Monroe · verified Sep 6
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    Leisure Lanes Monroe hosts a charity card-draw raffle presented by the South Central Tavern League, with proceeds benefiting the League’s SafeRide Program and local community efforts. Tickets are available at Cactus Co. Booze N’ Bites, The Depot, The Horseshoe Saloon, Leisure Lanes Monroe, Nett’s Sports Bar, and Sportsman’s Reloaded in New Glarus. Each $5 purchase equals one ticket, or get five for $20, and every ticket goes into the monthly drawing. If your name is selected, you choose a card for a payout... the Queen of Hearts awards 50 percent, any face card or ace pays 25 percent, and all other cards pay 20 percent, with additional prizes tied to the card you pick. Winners must be present to claim the main drawing, while consolation prizes do not require attendance. The raffle resets each month with a fresh deck, new tickets, and a new prize pool, so every drawing offers another opportunity to reveal the Queen of Hearts. In total, 40 percent of proceeds support charity and 60 percent are paid out in prizes.

    Event website ↗
Friday, November 6 1 event
  • 6pm

    L. A. Drive @ The Freeport Eagles Club #679

    Freeport, IL · verified Sep 6
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    This event offers a welcoming setting with an upbeat feel and plenty of quality tunes that keep the energy high. It centers on positive vibes and a comfortable atmosphere.

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Saturday, November 7 1 event
  • 6pm

    The Bark & Whine Ball

    The River’s Edge Experience, 103 S 1st St, Oregon · verified Sep 6
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    Celebrate the second annual Bark & Whine Ball at The River’s Edge Experience, a Hollywood Hounds themed evening that supports K9s. Enjoy live music from the Vodka Boys and barbecue prepared by Ralfie’s BBQ, with a focus on fundraising for four-legged friends. Dress to impress for a night of red carpet flair and good causes. Additional information will be shared closer to the event.

    Event website ↗
Sunday, November 8 1 event
  • 1pm

    Old Time Dance with David Austin Band

    1217 17th Ave, Monroe · verified Sep 6
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    This event is an old-time dance featuring the David Austin Band. Admission is $12. Seating is unreserved, first come, first served.

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Saturday, November 14 3 events
  • 8am

    Annual Craft & Vendor Fair

    1964 W Pearl City Rd, Freeport · verified Sep 6
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    Celebrate the season while browsing more than 40 vendors at the Annual Craft and Vendor Fair. Explore handmade creations, home decor, thoughtful gifts, baked treats, seasonal specialties, body care products, and other unique finds. Enjoy a welcoming shopping experience that highlights small businesses and helps you check off everyone on your list.

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  • 9am

    🪨✨ Northwest Illinois Rock Club’s 2026 Jewelry, Gem, Fossil, and Mineral Show! ✨🦖

    Eagles club #679, 542 N Turner Ave, Freeport · verified Sep 6
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    Explore a vibrant showcase of gems, minerals, fossils, and jewelry presented by the Northwest Illinois Rock Club. Watch demonstrations and learn from knowledgeable presenters, browse dealer booths and eye-catching displays to discover unique finds, and enjoy activities for kids, including a fish pond game and other games. It is also a convenient stop for holiday gift shopping, with additional attractions throughout the show. Admission is by free-will donation.

    Event website ↗
  • 11am

    4th Annual Coliseum Museum Book Fair

    124 N 4th St, Oregon · verified Sep 6
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    Attendees can meet authors at the 4th Annual Coliseum Museum Book Fair, with books spanning mystery, romance, children's literature, history, young adult, and more. For details or to request an application to display a book, call 815-595-5810 or email info@cmaaa.org.

    Event website ↗
Thursday, November 19 1 event
  • 7pm

    Brodhead Book Club

    Brodhead · verified Sep 6
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    The Brodhead Book Club brings together readers who enjoy thoughtful conversation and great books. The discussion of Heartwood by Amity Gaige takes place at the Brodhead Memorial Public Library, with guided questions that make it easy for both regular participants and first timers to contribute. Copies of the book will be available for checkout beginning in mid-October in standard print, large print, and Book on CD formats. New members are welcome to take part in a friendly conversation about the featured title.

    Event website ↗
Friday, November 20 1 event
  • 2pm

    GROUNDUP COMMUNITY – "FRESH FOR A CAUSE" FUNDRAISER 🔥

    223 S Chicago Ave, Freeport · verified Sep 6
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    A community-focused fundraiser turns a freshly prepared seafood meal into meaningful support for local programs. A $35 meal donation benefits GroundUP Community and Tensley Foundation Inc, advancing efforts that strengthen families, expand opportunity, and deliver essential help to neighbors in need. The menu features a choice of a four piece fillet fish dinner or a stuffed salmon dinner, prepared with quality ingredients and served with care. Proceeds power initiatives that include food assistance, workforce development, community outreach, and resources that help individuals and families thrive. One meal can move a shared mission forward and help build a stronger community, one plate at a time.

    Event website ↗
Sunday, November 22 1 event
  • 1pm

    Old Time Dance with Barefoot Becky & the Ivanhoe Dutchmen

    1217 17th Ave, Monroe · verified Sep 6
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    Admission is $12. Seating is not reserved and will be available on a first come, first served basis.

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Saturday, November 28 4 events
  • 3pm

    2026 Sip N Shop Vendor Fair

    The River’s Edge Experience, 103 S 1st St, Oregon · verified Sep 6
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    Explore a variety of vendors at the Sip N Shop Vendor Fair at The River’s Edge Experience, happening alongside the Oregon Candlelight Walk. Find one-of-a-kind gifts for the people who matter most, and pick up drinks available for purchase from River’s Edge Experience while you browse.

    Event website ↗
  • 6pm

    Mother of All Duos at Tipsy Hog

    TIPSY HOG, 101 S 3rd St, Oregon · verified Sep 6
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    Hear a set of classic rock favorites performed as covers, with familiar riffs and choruses that celebrate timeless rock.

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  • 6pm

    The Vodka Boys at Chrissy's Corner

    Chrissy's Corner, 17 N River Rd, Oregon · verified Sep 6
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    The Vodka Boys perform at Chrissy's Corner with a post-Thanksgiving hangover show that keeps the holiday weekend going.

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  • 7pm

    Ctrl Alt Dlt at Leisure Lanes

    Leisure Lanes Monroe, 2308 6th Ave, Monroe · verified Sep 6
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    Ctrl Alt Dlt presents an energizing get-together at Leisure Lanes designed to help shed Thanksgiving Day calories. It offers a fun way to get moving after the holiday.

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Tuesday, December 1 1 event
  • 6pm

    Tour of Hearts Charity Raffle @Bartels Tap

    Bartels & Co. Tap, 1014 17th Ave, Monroe · verified Sep 6
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    At Bartels & Co. Tap, the Tour of Hearts charity raffle features a monthly drawing that starts fresh each time with a new deck, new tickets, and a new prize pool. Tickets are available at Cactus Co. Booze N’ Bites, The Depot, The Horseshoe Saloon, Leisure Lanes Monroe, Nett's Sports Bar, and Sportsman’s Reloaded in New Glarus. Tickets cost $5 for one or $20 for five, and every purchase places your name into the monthly drawing. If selected, you pick a card to determine the payout. Drawing the Queen of Hearts awards 50 percent, any face card or an ace awards 25 percent, and all other cards award 20 percent, with additional prizes tied to the card you reveal. Attendance is required to claim the main drawing, while consolation prizes do not require being present. Each ticket helps fund the South Central Tavern League SafeRide Program and local community efforts, with 40 percent of proceeds going to charity and 60 percent returned as prizes. It offers a night out for a good cause and a chance to see whether the Queen of Hearts is in the cards.

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