A Year-Round Celebration of Arts, Culture, and Community

Monument Vintage antiques and collectibles 435 Main St. Bennington. Photo by Phil Holland.

Relax, and allow us to tell your fortune. As the New Year turns, you will begin to imagine the possibilities of a get-away to Bennington, Vermont. We see many getaways, because good things are happening in town (and around) throughout the year. We see snow, at last, and winter recreation, especially Nordic skiing at Prospect Mountain. We see cultural events at multiple venues that present live music and theater all year round. We see a choice of the many fine eateries that have opened downtown in recent years. We see seasonal fests and festivals happening all year long, and music in the open air, and craft beer, and people enjoying all that Vermont has to offer right here where it begins. Look into our calendar. Now, plan a trip — many trips! — to Bennington.

Year-Round Cultural Oases

Bennington Theater: A Stage for Every Season

Peter Antoniou, Psychic Comedian, performing to a sold-out audience at the Bennington Theater. Photo provided.

Throughout the year, Bennington Theater in Downtown Bennington hosts a range of events, including regular Trivia Nights, Wine and Improv, Cabaret Nights, Comedy Series, and the Monthly Benningtones series and theater plays. Delve into a world of creativity and laughter as the theater brings the community together through the magic of the performing arts.

Bennington Museum: Preserving History, Inspiring the Future


The Bennington Museum hosts a variety of events and exhibits throughout the year (April-December) that showcase the rich history of the town. From historical society events, and concerts in the courtyard to kids’ series, the Museum is a treasure trove of historical and contemporary knowledge and one of Bennington’s most beloved institutions.

Left Bank in North Bennington: A Haven for Art Enthusiasts

art gallery space bennington vermont

Throughout the year, Left Bank in North Bennington presents captivating exhibits that celebrate the arts. Visitors can marvel at the talent on display from local and regional artists alike in exhibits that showcase the unmatched creativity of the greater Bennington community. 

Monument Arts & Cultural Center: Where Creativity Takes Form

Photo by Jim Rogalski. MACCenter website.

Speaking of the performing arts, no trip to Bennington is complete without a visit to the Monument Arts & Cultural Center. With galleries and theatrical performances throughout the year, the MACCenter embodies Bennington’s commitment to creativity and the celebration of our vibrant cultural heritage. 

Little City Cider Company: Where Music and Cider Converge

Photo by Mark Schiffner

If locally made hard cider and rockin’ live music sounds like a recipe for a good night, then the Little City Cider Company is the place for you. This unconventional music venue hosts weekly open mics, drawing talented musicians from across the region. Check out their upcoming lineup on Facebook.

Seasonal Extravaganzas

Winterfest in North Bennington: A Frosty Fiesta of Fun

A man jumps into freezing Lake Paran during the Penguin Plunge at Winterfest in North Bennington Vermont
Come on in, the water’s fine! Photo credit: Lake Paran

Even when temperatures drop to single digits, Vermonters never miss a chance to get together and celebrate. Come help us revel in the beauty of winter on the 27th of January with Winterfest in North Bennington. This collaborative event features live music, craft fairs, delicious food, and the annual Lake Paran Plunge – an exhilarating experience for all ages.

Basement Concert Series: Bennington’s Rhythmic Heartbeat

Boston-based Session Americana at Bennington’s Little City Cider Co. Photo provided by Mark Schiffner

The locally iconic Basement Concert Series, presented by the Vermont Arts Exchange, returns with an even greater lineup of new artists. Experience the pulse of Bennington’s music scene and witness the magic unfold. Follow the VAE to stay in the loop about their upcoming dates and 2024 lineups.

Robert Frost Stone House Museum: Seasons of Poetry

Robert Frost Stone House in North Bennington Vermont
File photo.

Journey through the seasons at the Robert Frost Stone House Museum, open from June through October and November through April by appointment. Explore the exhibit and events that pay homage to one of America’s literary icons.

Homebrews: Southern Vermont HomeBrew Festival – Spring & Fall!

Bennington Vermont -Southwestern Vermont Hombrew Festival
Photo provided.

As spring unfolds, mark your calendar for the Southern Vermont HomeBrew Festival – Spring Edition on Saturday, May 4, 2024, from 12 PM to 4 PM. Join regional homebrewers as they showcase their craft with themed tastings, surprise food components, and fresh, unique brews. Keep an eye out for their upcoming Fall event date.

Summer Spectacles

Mayfest in Downtown Bennington: A Feast for the Arts

mayfest crowd vermont event arts and crafts fair Downtown Bennington Vermont
Photo provided.

Join us on Saturday, May 25, 2024 for Mayfest, a celebration of art, crafts, and community. Peruse the dozens of local vendors that line Main Street for the day, catch some live music at one of several stages set up throughout the event, and don’t forget to grab some fresh-squeezed lemonade to toast the return of Spring!

6th Annual Downtown Bennington Food Truck Festival

Downtown Bennington Vermont Food Truck Festival
Photo provided by the Bennington Banner.

This event is a must-attend for those who appreciate good food and vibrant community vibes. As the town of Bennington opens its streets to a lineup of diverse food trucks, attendees can indulge in a variety of delicious offerings, live music and a beer tent. 

27th annual NBOSS: The North Bennington Outdoor Sculpture Show

On June 29th, 2024, witness the 27th annual NBOSS – the largest outdoor sculpture show in the area. Enjoy over 50 sculptures, live music, free hotdogs, and accessible art for all ages from June through November.

Garlic Town, USA!: A Flavorful Finale Every Labor Day Weekend

Photos by Lorianna Weathers.

Bennington’s renowned Garlic Festival, produced by the Southwestern Vermont Chamber of Commerce, boasts over 125 vendors, live music, beer and cocktail tents, and garlic-themed entertainment. This festival is a pungent celebration of community spirit and diverse flavors. Garlic Town, USA gets bigger every year with more excitement and updates. In 2023, the event attracted more than 7,400 people to Downtown Bennington.

Quilt Fest: Stitching Stories, Crafting Art

Bennington Quilt Fest 2024, takes place on September 14 and 15, 2024, at Mount Anthony Union Middle School. Find yourself in a world of lively colors and intricate patterns, and discover the rich tradition of quilting.

11th annual Stone Skipping at Lake Paran: Ripples of Joy

Participate in the annual Stone Skipping event at Lake Paran in North Bennington, a family-friendly affair featuring food trucks and more, creating ripples of joy across all age groups.

Harvest Fest: Downtown’s Seasonal Showcase

Photos by Bennington Banner.

Usher in the fall season with Harvest Fest in Downtown Bennington on Saturday, October 19th. Indulge in food, partake in games, and revel in the lively atmosphere of downtown amongst the fiery fall colors that Vermont is famous for.

There! You have now seen the future, and it includes a visit – many visits! – to Bennington. We’re so glad you’ll be joining us in the celebrations of art, history, recreation, food and fun that make our town exceptional all year long. We look forward to seeing you in 2024!