Events in Bennington, VT

Enjoy a relaxed craft meetup where local and visiting makers can work on creative projects alongside friendly, like-minded, and sometimes delightfully silly community members. Bring a portable activity you love, whether it is knitting, crocheting, embroidery, painting, drawing, writing, hand spinning, chain maille, coloring, diamond painting, or even building with Legos, and settle in for some low-pressure creative time. This gathering is LGBTQ+ friendly and open to all. No registration is needed, and a Common Folk membership is not required.

Browse locally grown produce, bakery favorites, desserts, and handcrafted wares at a weekly market. It happens every Saturday and goes on regardless of the weather, so you can shop rain or shine.

Makers on Main is a marketplace with a mission, creating a lively hub that connects what happens in studios with the people who want to see it. It offers a professional setting where up-and-coming artists and established makers can share work, pilot fresh ideas, grow passion projects, and strengthen their place in the local economy. Vendor opportunities are available.

This 50-kilometer mountain bike ride makes a full loop around Mount Greylock on a mix of singletrack and doublewide trails, gravel roads, and a short stretch of pavement. The Thunderbolt Ski Runners are organizing the ride.

Tilly's Harvest Fest brings music, dancing, and activities to the parking lot at Tilly's Tap & Tavern at Valley Park Bowl. The lineup features a DJ, the Berkshire County Line Dancers, a bounce house, and Bowey the Magic Clown, with food available for purchase. Hosted by Tilly's Tap & Tavern. Vendors can apply online for space, with single 10x10 and double 20x20 options. The fee is $50 per 10x10 space.

This benefit barrel race awards points toward the Cambridge Saddle Club year-end awards. It is part of a nine-event series that includes five benefit barrel races and four weeknight jackpots, with results from this race counting toward the overall standings. Awards will recognize top riders in three age groups: Youth up to age 18, Middle ages 19 to 39, and Adult ages 40 and older. This is not a divisional format. In each group, the fastest time earns 10 points, the second fastest earns 9, and so on. There is no buy-in fee for awards eligibility, and riders must be Cambridge Saddle Club members to qualify.

Build practical mending skills in a friendly repair club led by repair specialist @thesensiblesheep. This drop-in gathering offers a welcoming space to learn techniques that help clothes last longer. A sewing machine will be set up, and attendees can bring their own projects to repair alongside others or seek guidance on how to fix them. This program is funded in part by the Local Cultural Council of the Northern Berkshires, with support from Mass Cultural Council.

At Bennington Museum, curator Jamie Franklin offers a guided tour of the exhibition Vermont Vice, on display through November 1, 2026. Expect highlights from the show and insight into how and why each piece was selected to illuminate the darker side of Vermont. The talk is included with regular admission and no registration is required.

Outpost 40 hosts a live solo acoustic performance by Jason Irwin, paired with dinner and drinks. The setting is family friendly.

This experience blends gentle movement with intuitive exploration. The evening opens with a calming, seated yoga practice to settle body and mind, then continues with a group tarot session led by psychic intuitive Wendy Bordwell of B.Well Insights. The atmosphere encourages rest and reflection, complemented by light refreshments that support a friendly sense of community. Suitable for all experience levels, each attendee receives a short introductory reading with the option to schedule a more in-depth one-on-one session with Wendy at a later time.

A stand-up show featuring Jason Salmon, a Texas born, New York City based comic whose style has been compared to getting the best guidance from the most lovable fool. He has performed around the world, including shows for troops in Europe, South America, and Afghanistan, and his hour special BISCUITS and GRAVITY can be watched on YouTube. Credits include Red Dead Redemption 2, Orange is the New Black, HBO, Comedy Central, At Home with Amy Sedaris, Hulu’s Wu Tang Clan Series, and 30 Rock.

Costumes are encouraged for this all-ages gathering. Lead-line and peewee classes are included, welcoming the youngest participants alongside adults.

Preschoolers get creative with simple printmaking, experimenting with materials like cotton swabs, styrofoam, and plants to make their own prints. Expect a delightfully messy experience with lots of ink and paint, so wear clothes that can get dirty. Part of Museum ABCs, a collaboration between Bennington Museum and the Bennington Free Library, this program is designed for children ages 3 to 5 with their adult companions, and siblings are welcome. The series includes artwork, stories, and more. Admission is free thanks to funding from The Bank of Bennington. Sponsored by The Bank of Bennington.

Cookbook Club offers a welcoming space to share food and recipes.

TIW comes back for a night of wrestling, highlighted by its yearly rumble featuring 40 participants.

At Greylock Glen Center in Adams, MA, this one day showcase highlights the skill and creativity of the region’s woodworkers. Explore handcrafted wood pieces from artisans across the area at a market style event, and connect with organizations focused on strengthening the local wood economy. Whether you are searching for a distinctive gift or looking to support local makers, there is something for everyone.

This lively improv workshop offers a playful way for adults to get creative, connect, and share some laughs. Guided by Stephanie Phelan, an experienced performer, director, and teacher, it starts with the basics and moves through games and exercises that progress at the group’s pace. No experience is required, there is no pressure to perform, and the focus stays on encouragement, fun, and the possibility of new friendships. Drinks and snacks are available at the bar. Admission is $10.

Set out on Vermont’s Long Trail for a group backpacking loop covering 21.1 miles. The route winds through deep forest, visits scenic overlooks, passes quiet ponds, and climbs to the tops of two peaks. Expect short instructional segments to build backcountry skills while the main focus remains an exciting, shared adventure. This outing welcomes all experience levels. It suits a fit beginner, an intermediate backpacker looking to refine skills and update gear, or an experienced hiker seeking a refresher or a new challenge. Participants should be ready to hike up to 11 miles in a day on varied terrain with occasional increases in intensity, spend a full day on trail carrying a pack weighing more than 20 pounds, and go off trail at times to practice navigation. Group size is limited to five and an RSVP is required. The trip runs rain or shine. A waiver and assumption of risk must be completed before taking part and can be signed electronically or in person on the day of the trip. For questions, contact Mat at matjobin@reachyoursummit.net. Included are backpacking guiding and instruction, required National Forest or campsite permits and reservations, breakfast and dinner, two one liter bottles of water and two snacks, and a free product. Individual gear rentals are available for items such as a tent, sleeping pad, sleeping bag, pillow, headlamps, cook kit, stove, fuel, water filter, water treatment, bear bag kit, trekking poles, compass, and maps. Transportation is not included. A park entry fee may be required and is not covered. Personal gear like a backpack, clothing, and footwear, as well as personal supplies such as hygiene items, electronics, and reading material or other entertainment are not included, and additional snacks or food are up to you.

VNA & Hospice of the Southwest Region presents Death, Dying, & Danishes, a welcoming discussion group guided by hospice volunteers. Conversations focus on end-of-life topics and grief, building comfort with talking about death and encouraging living fully. Coffee, tea, and treats help create a relaxed setting where community members of all ages can bring questions, experiences, and reflections for open, supportive dialogue. The gathering is free and open to the public, and purchases that support host sites are appreciated. For more information, contact Ed Keating at 802-445-5520 or ed.keating@vnahsr.org.

Celebrate the season at a fall festival in downtown Bennington, Vermont, featuring live bands, great food, and family friendly entertainment. Enjoy the music and autumn atmosphere in the heart of town.

Swap your completed puzzles for different ones, or stop in even if you do not have any to trade and pick out a few to enjoy. This casual exchange is all about sharing puzzles and finding something new to take home.

Create art with pressed botanicals in a hands-on workshop connected to Art from the Garden and Ellie Roden’s Creating with Pressed Flowers. Materials are provided, and the fee is $35.

A relaxed gathering centered on music with a bright and upbeat atmosphere.

Explore Bennington’s past on a guided walk through the Bennington Centre Cemetery led by Bennington Museum curator Jamie Franklin. The experience begins in the Museum’s Early Vermont gallery, where you will see the headstone of Jedidiah Dewey, Bennington’s first pastor, carved by Frederick Manning, and learn about some of the earliest gravestones created in the area. The group then continues into the burial ground behind Old First Church to hear stories of those interred there and to look at examples of work by the region’s early headstone carvers. Wear sturdy shoes and be ready for uphill sections and uneven ground. Bringing water and using sunscreen and bug spray is recommended. Tickets are $20 for Bennington Museum members and $27 for Not-Yet-Members, available on the Museum website, with tickets also offered at the door if space allows.

This family friendly craft fair brings the community together around shopping, delicious food, creativity, and local support. Organizers are welcoming food vendors, artisans, bakers, boutique sellers, and small business owners. Handcrafted creations, boutique finds, jewelry and skincare products, candles, personalized gifts, sweet treats, specialty foods, and dishes from a variety of culinary traditions are all a great match. Prospective vendors can email ccsteakscake1986@gmail.com and should include a business name and product photos.

Now in its fourth year, this holiday craft market takes place at MAUHS in Bennington, Vermont. Prospective vendors can contact Christina at Cgabrus@svsu.org to learn about participating.

TIW is back, delivering another night of wrestling action.

At Bennington Free Library, this follow-up workshop is tailored for people who have already started their Advance Directive and want help bringing it to the finish line. The focus is on completing and signing your document. There is no formal presentation, and facilitators will be on hand to work with you and answer questions. Please bring your partially completed form along with any questions you may have. If you complete your Advance Directive during the session, facilitators can serve as witnesses when you sign. Scanning capability is planned so a PDF of your completed, signed, and witnessed form can be emailed to you for sharing. These free community workshops are designed to help you complete the VT Ethics Network Short Form Advance Directive with clear guidance, reassurance, and practical support. Each workshop runs for two hours and is open to the public. Advance sign-up is requested to reserve a seat and ensure sufficient materials. For information or to register, contact Ed Keating at ed.keating@vnahsr.org or 802-445-5520.

An open, welcoming community conversation focused on death, dying, and end of life care takes place at the Whitingham Free Public Library. Participants can learn about free hospice resources, green burial options, advance directives, financial planning, and related topics. The format invites questions and personal stories in a caring setting. Hospice volunteers will share information about no cost services available locally, and Whitingham resident Katherine MacLean will facilitate a thoughtful, compassionate dialogue for anyone who wants to speak or simply listen. Light refreshments will be available.

At Bennington Museum, children can bring a toy they love to examine what it is made from, then take a playful look back at the kinds of toys kids enjoyed in earlier times. Together they will compare materials, consider whether older toys needed charging, and reflect on how fun they were to use. Museum ABCs is a collaboration between Bennington Museum and the Bennington Free Library created for children ages 3 to 5 with an adult companion, and siblings are welcome. The program features art activities, stories, and more. Admission is free thanks to funding from The Bank of Bennington. Sponsored by The Bank of Bennington.

VNA & Hospice of the Southwest Region offers a community conversation called Death, Dying, & Danishes at Bennington Community Market. Guided by hospice volunteers, this gathering creates a welcoming setting to speak openly about mortality, grief, and the ways we choose to live fully. Coffee, tea, and treats help set a relaxed tone for thoughtful dialogue. People of all ages are invited to bring questions, experiences, and reflections. The purpose is simple... provide a comfortable forum where neighbors can connect and discuss life, dying, and loss with honesty and care. There is no cost to attend and everyone is welcome, and supporting purchases at the host site are appreciated. For more information in advance, contact Ed Keating at 802-445-5520 or ed.keating@vnahsr.org.

TIW marks a decade with a special anniversary event to celebrate this milestone.

VNA & Hospice of the Southwest Region offers a community discussion on death and dying at Bennington Community Market. Led by Hospice volunteers, Death, Dying, & Danishes provides a welcoming setting with coffee, tea, and treats for candid conversation about life, loss, and grief. The focus is to build comfort with a difficult topic while encouraging people to make the most of their lives. People of all ages can bring questions, experiences, and thoughts to share. This gathering is free and open to the public, and purchases in support of the host site are appreciated. For more information beforehand, contact Ed Keating at 802-445-5520 or ed.keating@vnahsr.org.

Swap the usual paint-and-sip for a sweet spin where cake becomes the canvas. Hosted by Delectable Delights by Tarolyn at The Loft at Driskells, this hands-on class teaches buttercream painting as you transform a pre-iced 6-inch cake into an edible work of art. All decorating tools, food-safe brushes, and a palette of colored buttercream are provided, along with step-by-step guidance that welcomes both first-timers and seasoned bakers. Enjoy a tea and lemonade bar with flavored teas and handcrafted lemonades plus light refreshments while you create. Capture the moment with photo opportunities, then take your finished cake home in the included box. Crafted as a cheerful holiday experience, it suits a friends night out, a date, or a family activity.