Events in Nicholasville, KY

A coffee chat with the Chamber at Woodford County Library highlights lively conversation on community topics.

Mac-a-Tude brings a comfort-food lineup to Irvine Mcdowell Park for Tasty Tuesday. Dig into loaded mac and cheese bowls and fresh wraps, pair them with handcrafted flavored lemonades, energy drinks, bubble teas, and dirty sodas, and finish with loaded cheesecakes. Live music and a welcoming community atmosphere round out the experience.

Admission is free at Ceremony Point. After class, relax at the Welcome Center with a glass of wine and a charcuterie spread.

This meaningful and fun day of golf directly supports youth by providing the resources they need to build brighter futures.

Downtown Days transforms downtown Nicholasville into a three day celebration of music, food, shopping and interactive fun. The weekend features live performances, the Main Street Market, a barbecue competition where teams also sell what they cook, a beer and wine garden, Squonk’s JOY MACHINE, Kentucky Proud farm and garden vendors, Chalk Fest, Classic Cars on Main, community line dancing and clogging, a family movie, a dedicated Kids Zone and Safety City, and a wide range of competitions and activities. There is plenty to eat throughout the district, and even the Oscar Mayer Wienermobile adds to the festivities. Full schedules for each day are posted on the event page, with some activities limited to specific windows, and plans may shift as the weekend unfolds. Updates will be shared there as needed, and official applications or ticket purchases are handled only through Downtown Days and Nicholasville Events forms, not through private messages or unsolicited comments.

At White Hall State Historic Site, this inaugural 5K and 1-mile Hope Stride brings people together to reduce stigma and nurture hope around suicide prevention and mental health. The evening features a serene water lantern launch on the pond, then participants can run the 5K or choose the shorter stride. All donations support the Behavioral Health Department at Baptist Health Richmond, advancing accessible care and a more supportive, connected community. If you or someone you know is in crisis, call or text 988 to reach the Suicide & Crisis Lifeline at any time.

Hosted by Woodford Post 67 of The American Legion Family, this second annual Roper-themed celebration supports the Woodford County Food Pantry. Attendees are encouraged to dress as Mrs. Roper or Stanley Roper as the Post adopts a playful Reagle Beagle vibe. The event features dinner, 70s-themed SINGO, food and drink specials, dancing, and sing-alongs to favorite hits. A costume contest adds friendly competition, and the event is open to everyone.

Experience a bustling marketplace in Lunenburg, Nova Scotia, where artisans, local food, and live entertainment come together. More than 150 vendors will be set up across multiple buildings, with an additional building added for 2026. Enjoy live music and outdoor tents, and sample flavors from food trucks and specialty producers. Shop for handmade work by Nova Scotian makers, including pottery, woodworking, glass art, textiles, home decor, jewelry, and more. Treat yourself to baked goods, fudge, nuts, and beverages, and discover local wines alongside other specialty foods. Admission includes a weekend pass bracelet so returning is easy. Cash is recommended for the smoothest experience. Only service dogs are permitted inside buildings. For more information, email Sabcreationkey50@gmail.com.

Dive into a dog-friendly pool day planned by Jessamine County Animal Care & Control and Jessamine County Parks & Recreation. The water opens to canine swimmers for playtime, with the addition of lighthearted contests that include Corgi races and a Dachshund derby. All dogs are welcome to enjoy open swim, and proof of a current rabies vaccination is required for participation. Pack a camera and a playful spirit for a splash-filled outing with plenty of wagging tails and community cheer. Further details and registration information will be shared as planning continues.

This year the annual event gets a refresh with the addition of a car show. A speaker is included, along with other activities.

The Annual Twilight Festival is approaching, and vendor opportunities are available. Early bird registration is open now, and for this event vendor payments go only to Woodford County.

Enjoy a lively horse show at the Pioneer Saddle Club featuring classes for gaited and non-gaited horses. Concessions will be available for purchase. Highpoint awards are included, with full details on the back of the showbill. The showbill can be found on the event’s Facebook page. All horses entering the grounds must present a negative Coggins test.

EKU takes on Chattanooga in a Maroon Out football game at Roy Kidd Stadium. Spectators are encouraged to dress in maroon to display EKU pride. The event is presented by Coca-cola.

Sheldon Road appears at Neon Nights Bar in Nicholasville, Kentucky for an upbeat evening that promises plenty of fun.

The fourth Chenault Farmers Market of the season brings local growers and makers to the Welcome Center parking area at Chenault Vineyards. Browse a range of vendors, including farmers and artisans from Madison County’s Farmers Market Association alongside participants from Berea, Richmond, and Garrard County. After shopping, enjoy lunch at the Welcome Center, relax on the patio, and take in the vineyard setting. Vendors interested in participating can text FARMERSMARKET to 859-328-7773 for more information.

Now in its 26th year, this Haven Care Center fundraising banquet celebrates a theme of peace and steadfast trust, inspired by Isaiah 26:3. It takes place at the Conover Athletic Center at Campbellsville University Harrodsburg.

A Together RKY community spotlight at Chenault Vineyards will put the focus on Operation Christmas Child, while also bringing attention to pressing issues in Richmond, Kentucky, including hunger, addiction, human trafficking, homelessness, and incarceration. Additional details will be provided as plans are confirmed.

Discover what the Kiwanis Club of Richmond, KY Inc. does to support children, serve others, and build a stronger community. This regular meeting at Madison County Public Library offers a chance to learn about the club’s mission and how it makes a difference locally, along with ways to connect with people who want to give back. Guests are welcome.

The 2026 Jessamine Fall Festival has confirmed its dates. Look to the festival website for more information and updates as the event gets closer.

Exile leads a full evening of live music at The Vine at Chenault Vineyards, with Brassfield opening the show. Entry begins ahead of the performances so attendees can arrive and get settled, then the night flows from the opener to the headliner.

This 5K run and walk raises funds for God's Outreach Food Pantry Backpack Program. Registration takes place before the race, which begins promptly.

A relaxed group float at Lake Reba Park’s kayak launch welcomes beginners and experienced paddlers alike. A person will be on site to offer tips if needed. Kayak rentals are free, and boats are available on a first come, first served basis.

EKU faces Dayton at Roy Kidd Stadium with a game day centered on young fans. Children 12 and under can receive one complimentary ticket. During halftime, kids 12 and under can take part in a run across CG Bank Field with the Colonel. A Kids at the Kidd themed T-shirt design contest will award the winner the finished shirt for themselves and their family, complimentary family tickets to the EKU vs. Dayton game, and seating in the Coke Thirst Zone.

Enjoy a live performance by Westley Metcalfe at Chenault Vineyards. The show takes place in the Welcome Center, and admission is free.

Versailles, Kentucky hosts an annual, community-driven celebration that channels cozy small-town spirit, quick-witted chatter, bottomless coffee and a shared love of storytelling. Local businesses bring the town to life for an immersive weekend, welcoming fans and visitors to explore a place where connections come easily, traditions are cherished and something is always percolating. Expect themed shopping and pop-up experiences, special menus, charming photo spots, gatherings for book lovers and nostalgic surprises tucked around every corner. It is designed to feel like stepping into a beloved comfort show... only this time it is real and you are part of it.

This Lunch and Learn focuses on homeownership and real estate investing. Banking experts explain mortgage basics, how home equity lines of credit work, and practical ways to finance investment properties in clear, accessible terms. It is designed for first time buyers, homeowners interested in leveraging equity, and anyone evaluating investment opportunities. Expect straightforward guidance and useful takeaways to support confident financial decisions.

An annual, community-led celebration in Versailles brings the spirit of Stars Hollow from Gilmore Girls to life, drawing on cozy small-town charm, quick-witted banter, countless cups of coffee, and a shared love of stories. Versailles businesses collaborate to create an immersive experience that welcomes fans and curious visitors alike. Throughout the weekend, attendees can browse themed shopping and pop-ups, enjoy special menus, discover photo-worthy spots, join gatherings for book lovers, and uncover nostalgic touches throughout town. The goal is to make it feel like stepping into a beloved comfort show, with the experience unfolding all around you. At its heart, the weekend celebrates community, with local shops teaming up, neighbors greeting visitors, and fans connecting in a place that feels like home whether it is a first visit or a return. Coffee in hand, take a leisurely stroll along Main Street and linger for a while.

Boone's Trace Grill hosts an interactive night that begins with Music Bingo and continues with karaoke. Players receive bingo cards printed with song titles while the host plays 30 to 45 seconds of each track and announces the name, and you mark it if it appears on your card. Music Bingo is free to play, with two rounds offering $25 and $50 jackpots. After the games, karaoke takes the spotlight for more music, laughter, and friendly competition.

The Woodford County Board of Education holds its monthly meeting at the Woodford County Public Schools Central Office. Community members may attend in person or watch a live video stream on the district’s YouTube channel, rather than on Facebook. Simmons Elementary is the featured school for this session. Anyone wishing to offer public comment must be present at the meeting and sign up at the entrance before the meeting begins, listing their name, address, and the specific agenda item they plan to address. Each comment is limited to three minutes and must relate to an item on the agenda.

This bike tour includes tastings and visits at distilleries such as Woodford Reserve, Buffalo Trace, and Four Roses. It also features a stop at Shaker Village to learn about farm-to-table agriculture and culinary practices.

Hosted by Nic Cassetta at the Welcome Center, this showcase spotlights live sets from local musicians who have performed at earlier open mic nights. Admission is free.

Main Street comes alive for the Kentucky Heritage Jazz Festival kickoff, blending the spirit of New Orleans with an evening of music, food, and community. Enjoy live jazz, NOLA-inspired flavors, local vendors, family-friendly fun, and activities for kids. The Circle City Sidewalk Stompers, a returning crowd favorite, bring their playful clown band energy alongside more New Orleans sounds filling downtown. This celebration on Main leads into the Kentucky Heritage Jazz Festival at Old Fort Harrod State Park.

Mac-a-Tude will be serving at the Millstone Festival in downtown Richmond with a comfort-filled menu that includes loaded mac and cheese bowls, handcrafted flavored lemonades, bubble teas, energy drinks, dirty sodas, and loaded cheesecakes. The festival is Richmond’s annual autumn celebration in the historic Mill District and around the courthouse square, showcasing Madison County with live entertainment, food and spirits, and activities for all ages. Visitors can browse rows of local vendors, discover handmade goods, and enjoy performances throughout the day in a lively, community-focused setting.

The Millstone Festival takes place in downtown Richmond. Vendor applications are closed and submissions received before the deadline are being reviewed, and those applicants will be contacted once that process is complete. A waitlist option is available, and paperwork may still be submitted to be considered; notification will be sent by email if accepted. Please wait to pay until acceptance is confirmed. Accepted participants will receive an invoice for a $50 event fee plus a $25 late fee. For questions, call (859) 623-8753 or email parksandrec@richmondky.gov.

Experience two days of live jazz, food, and fun at historic Old Fort Harrod State Park as the Kentucky Heritage Jazz Festival showcases 15 regional and national ensembles. Admission is free for all performances, and festival attendees may also tour the historic fort at no charge on both days. Saturday highlights feature regional and national jazz combos, while Sunday spotlights collegiate big bands, with additional performances throughout the weekend. This outdoor event takes place rain or shine, so check the forecast and plan accordingly. Small pop-up tents and umbrellas are permitted in designated areas at the park, and personal lawn chairs are welcome for seating. A Taste of New Orleans kickoff on Main Street in historic Harrodsburg brings NOLA jazz, NOLA food, and family fun to set the tone for the festivities. The Kentucky Heritage Jazz Festival is presented through the support of sponsors and donors under the Mercer Chamber Foundation, Inc., 501c3.

Family Weekend features a day centered on football and time together. The occasion also highlights a 1979 to 1982 team reunion, recognizing players from the 1979, 1980, 1981, and 1982 teams who made four consecutive national championship appearances and captured two national titles. It brings families and past team members together to honor on-field achievements and the spirit of the game.

five below band performs at Bluegrass Barrel House.

Explore the mission and work of Kiwanis Club of Richmond, KY Inc., including its focus on children, commitment to service, and efforts to strengthen the community. Whether your goal is to give back, connect with others, or simply learn more about the club, guests are welcome.

Experience a bustling craft marketplace in Lunenburg, Nova Scotia, featuring more than 150 vendors across multiple buildings, including a newly added building for 2026, plus outdoor tents and live music. Browse handmade pottery, woodworking, glass art, textiles, home decor, jewelry, and other creations from Nova Scotian artisans and makers. Enjoy local flavors from food trucks on both days along with baked goods, fudge, nuts, specialty foods, beverages, and local wines. Admission includes a weekend pass bracelet. Only service dogs are permitted inside buildings. Having cash on hand is recommended. For inquiries, email Sabcreationkey50@gmail.com.

The event recognizes the 2026 EKU Athletics Hall of Fame induction class and celebrates their achievements.

The season’s final Chenault Farmers Market takes place at Chenault Vineyards, with vendors setting up in the parking area by the Welcome Center. Browse an assortment of farm-fresh goods and handcrafted items from growers and makers connected to Madison County’s Farmers Market Association, along with participants from Berea, Richmond, and Garrard County. After shopping, enjoy lunch at the Welcome Center, relax on the patio in the sunshine, and spend a laid-back afternoon amid the vineyard setting. Interested in having a booth? Text "FARMERSMARKET" to 859-328-7773 for details.

A patio performance brings live tunes to Chenault Vineyards.

Experience dynamic community conversations that encourage open dialogue and the exchange of ideas. The emphasis is on thoughtful discussion and active listening to foster connection.

Zach Williams appears at EKU Center For The Arts in Richmond, Kentucky.

At Boone's Trace Grill, enjoy a Halloween-themed trivia night filled with laughs, friendly competition, and family bonding. Gather a team of family and friends to test knowledge, teamwork, and wit by guessing the most popular answers to survey questions. New and seasoned players are welcome. Look forward to team sign-ups, prizes for the winning team, and food and drink specials available all night. The lively atmosphere is perfect for creating memories. RSVPs are encouraged.

Hosted at Chenault Vineyards, Together RKY will present a spotlight on local nonprofits and the urgent challenges facing Richmond, Kentucky, such as hunger, addiction, human trafficking, homelessness, and incarceration. Additional details will be shared soon.

Held at Madison County Public Library, this meeting introduces the Kiwanis Club of Richmond, KY Inc. and its work supporting children, promoting service, and strengthening the community. It is open to people interested in giving back, connecting with others, or learning more about the club’s mission. Guests are welcome.

This event is free to attend and will be hosted by Nic Cassetta in the Welcome Center. Attendee sign-ups are available inside the Welcome Center.

A community-focused expo celebrating small businesses and the big dreams behind them. Centered on growing together, this gathering highlights entrepreneurship and encourages meaningful support for local enterprises and the people who power them.

Homecoming at Roy Kidd Stadium features EKU Football taking on West Florida and celebrates Colonel pride with traditions, reunions, and EKU Athletics highlights. Students, alumni, families, and fans can reconnect, make memories, and cheer for the Colonels. During halftime, the Homecoming King and Queen will be crowned, marking a centerpiece of one of EKU’s most spirited weekends.

Wear a Halloween costume for a parade, then take part in trick or treating in the orchard. This family friendly celebration offers a festive atmosphere with a focus on safety.

Book Club at Woodford County Library features a discussion of The Island of Missing Trees by Elif Shafak. This fiction novel, published in 2021 and 368 pages long, explores the repercussions when two Cypriot teenagers, one Greek and one Turkish, fall in love on the eve of war between their communities.

The Woodford County Board of Education holds its monthly meeting at the Woodford County Public Schools Central Office. The session is open to the public with in person attendance and a live video stream on the district’s YouTube page, and it will not be streamed on Facebook. Woodford County Middle School will be highlighted during the agenda. Individuals who wish to speak during public comment must attend in person and sign in at the entrance before the meeting begins, providing their name and the agenda item they plan to address. Comments must relate to items on the agenda.

Boone's Trace Grill hosts a Halloween-themed evening with Music Bingo followed by karaoke. Players receive a bingo card with song titles while the host plays 30 to 45 seconds of each track and then announces the title so participants can mark matches. Music Bingo is free to play and features two rounds with $25 and $50 jackpots. A kids costume contest is also part of the festivities.

This regular meeting at Olive Garden (Richmond Centre) highlights the mission of the Kiwanis Club of Richmond, KY Inc., including its commitment to children, a heart for service, and ongoing efforts to strengthen the community. Attendees can learn more about the club, explore ways to give back, and connect with others who value service. Guests may attend.

The evening at Boone’s Trace Grill features a survey-based Family Feud game at no cost to play, with teams guessing the most popular answers and prizes awaiting the top finishers. After the game concludes, karaoke follows, giving performers a chance to take the mic and sing favorite tunes. Food and drinks are available, setting the tone for laughs and friendly competition.

Coffee with the Chamber at Woodford County Library centers on a lively community conversation, offering an open space for dialogue and connection.

This gathering at Anderson Dean Community Park honors those who sacrificed their lives for our freedom with a commemorative ceremony, followed by a 6.6 mile ruck march. After the march, there will be exhibits and demonstrations, with coffee and food trucks on site. Open to all.

The Branch: A Dance Experience offers more than a typical convention. It centers the person behind the dancer by weaving movement, mindset work, and open conversation into an atmosphere that nurtures confidence, growth, and genuine self expression. This judgment free environment helps rekindle the original joy of dance. Season 5, titled EMBER, focuses on tending the inner flame. Even a small ember holds heat and the power to spark something greater, and this theme invites standing in personal strength, moving through fear, committing to growth, and showing up boldly in class and in life. Expect to move, take time to reflect, and leave with a renewed spark from within.

EKU Football faces Central Arkansas at Roy Kidd Stadium in a game that also celebrates Senior Day and a Salute to Service. The day honors the EKU Football senior class and recognizes veterans, active duty military, first responders, health care workers, and their families.

An evening with Sheldon Road at Neon Nights Bar in Nicholasville, Kentucky promises a great time.

The Woodford County Board of Education will hold its monthly meeting at the Woodford County Public Schools Central Office. Community members can attend in person or watch a live video stream on the district’s YouTube page. The meeting will not be streamed on Facebook. Woodford County High School will be highlighted during the session. If you wish to offer public comment, you must attend in person. Please sign up at the entrance by providing your name, address, and the specific agenda item your remarks address. Registration must be completed before the meeting begins. Comments are limited to three minutes and must relate to an item on the agenda.

Pre-registration is required for this hands-on Winter Crushed Glass Suncatcher class in Perkins Building, Room 219. Participants create a 12-inch suncatcher with colorful crushed glass while learning techniques for layering, blending textures, and finishing with resin for a luminous look. Four design options are available: Snowman Trio, Winter Cardinal, Quilt Square, or Vineyard Reflection. No prior experience is needed, and each project is one of a kind. Everyone leaves with a finished piece to display at home or give as a handmade gift. The cost includes a $25 registration fee, plus a $45 supply fee paid to the instructor at the beginning of class. Adults ages 65 and older are eligible for free classes and can register by calling 859-622-1228.

Learn about the Kiwanis Club of Richmond, KY Inc. and how it is helping in the community through its focus on children, service, and strengthening community ties. This is a welcoming opportunity for anyone who wants to give back, make connections, or simply find out more about the club’s efforts. Visitors are welcome.

An interactive night of Music Bingo at Boone's Trace Grill features bingo cards filled with song titles. The host plays short clips and says each song name, and players mark their cards when they have a match. There is no charge to participate, and two rounds award $25 and $50 jackpots. After the bingo fun, karaoke keeps the music going. Food and drinks are available, creating a relaxed setting for friends and anyone who enjoys lighthearted competition.

EKU Center for the Arts hosts a candlelit rock spectacle where a 14-piece ensemble of classical musicians reimagines legendary rock and metal anthems. Across a 90-minute program, expect sweeping strings, soaring vocals, and surges of distortion that merge classical finesse with hard-hitting power. The rotating collective performs music from artists such as Metallica, AC/DC, the Rolling Stones, Rage Against the Machine, My Chemical Romance, Linkin Park, System of a Down, Guns N Roses, Evanescence, Papa Roach, and the Cranberries. Audience feedback highlights a unique blend of classical bravado and hard rock, with an average rating of 4.7 out of 5. The Rock Orchestra and its events are not affiliated with the original artists or composers, and all trademarks are the property of their respective owners.