October in Bennington Vermont, Vermont: Fall Colors, Harvest Fest and Halloween

October brings fall color, seasonal flavors, and plenty of reasons to spend time in Bennington, Vermont. While foliage is still developing across the state, the early fall season continues to draw visitors looking to enjoy the colors before peak foliage crowds arrive.

From Downtown Bennington’s annual Harvest Fest to Halloween celebrations, a new film festival, and seasonal dining, October offers plenty of ways to explore the region.

Fall Foliage: Enjoy the Colors Before Peak Season

Fall color continues to develop across Vermont as October begins. After welcoming visitors throughout September who came to enjoy early foliage and avoid the busiest weeks, Bennington remains a great destination for an autumn getaway.

Early October is another opportunity to explore scenic drives, mountain views, local trails, and the changing landscape before peak foliage arrives. Take your time discovering the region, then head downtown for local shopping, dining, and a taste of Southern Vermont’s fall season.

Planning a visit? Explore our outdoor recreation guide for trails, parks, and scenic destinations around Bennington.

Harvest Fest: A Fall Celebration in Downtown Bennington

Saturday, October 17 | 10 a.m.–5 p.m. | Downtown Bennington

The 5th annual Harvest Fest is shaping up to be a special day in Downtown Bennington, with a lineup of vendors, entertainers, and activities for all ages.

This year’s highlight is the Kids Zone, where children can make their own scarecrows and take home a seasonal creation. Visitors can also browse local vendors, enjoy the festive atmosphere, and explore downtown businesses throughout the day.

Whether you’re visiting with family, meeting friends, or spending a fall weekend in the Shires, Harvest Fest is a chance to experience the community spirit of Bennington.

Make a day of it: Discover more downtown shopping, dining, and destinations at VermontBeginsHere.com.

Halloween in Bennington: Parades, Costumes and Community Fun

October brings Halloween celebrations throughout the Bennington area, with opportunities for families and visitors to enjoy the season together. Or simply by driving around and admiring the beautiful homes and Bennington’s rich architecture, complemented by spooky decorations.

North Bennington Halloween Parade

Led by Vermont Arts Exchange, the North Bennington Halloween Parade brings the community together for a celebration of colorful costumes, live music, and a gathering afterward at Lion’s Park.

The 34th annual parade will take place on Saturday, Oct 31st at 3PM. Check Vermont Arts Exchange for updates as Halloween approaches.

Banner & Coggins Trunk or Treat

What happens when a local newspaper and a local car dealership team up for Halloween? Two decorated showrooms, more than 30 community trunks handing out candy, and an entertainment area for families to enjoy.

The Bennington Banner and Coggins Honda/Toyota bring this community event together for a safe, welcoming place to dress up, collect candy, explore the decorated showrooms, and enjoy a little Halloween fun.

See the full community calendar here.

Film and Folklore: A New Chapter for Bennington’s Arts Scene

November 5–8, 2026 | Downtown Bennington (multiple locations)

Vermont Begins Here recently sat down with Bennington Theater Executive Director Kaiya Kirk to discuss the upcoming Vermont Film & Folklore Festival, which will make its home in Downtown Bennington this year.

The four-day festival celebrates storytelling through film, bringing together featured films, independent submissions, and filmmakers from around the country, including a group of Vermont-based filmmakers.

The festival’s anchor films include:

The Trial of Alec Baldwin, directed by Rory Kennedy

Knife: The Attempted Murder of Salman Rushdie, directed by Alex Gibney

I Shot Andy Warhol, directed by Mary Harron

Alongside these featured films, the festival will showcase more than 30 filmmakers and a selection of short films. Each day features an anchor film and additional screenings, with the festival concluding with an awards ceremony.

Co-founded by Tim Rhys and Karol Martesko-Fenster, the festival explores the role of storytelling in shaping shared values while supporting exceptional voices in film and beyond.

Kirk said the festival is a natural addition to Bennington Theater’s programming and the community’s creative life, bringing outstanding films from around the world to Southern Vermont while highlighting filmmakers working closer to home.

Plan your visit: All-access passes and day passes are available now. Individual screening tickets, the full lineup, and the complete schedule will be announced in the coming weeks at BenningtonTheater.org.

Seasonal Flavors and Views: Where to Eat and Drink in Bennington

Fall is a great time to explore Bennington’s local dining and drinking destinations, from seasonal beverages to restaurants with views of the surrounding landscape.

In Downtown Bennington, Madison Brewing Company and The Coffee Bar offer seasonal drinks to enjoy as you explore the shops and streets.

For a meal with a view, consider Pangaea Lounge, the Publyk House, or the Mount Anthony Country Club. Each offers a different setting for taking in the region while enjoying a meal.

And these are just a few of the options. Bennington’s dining scene includes a range of restaurants, cafés, breweries, and gathering places worth discovering throughout the season.

Explore more: Browse VermontBeginsHere.com for dining and drinking destinations throughout Bennington and Southern Vermont.

Plan Your October Getaway

Whether you’re chasing early foliage, exploring Downtown Bennington during Harvest Fest, celebrating Halloween, or planning ahead for the Vermont Film & Folklore Festival, October offers plenty of reasons to visit.

Explore more places to stay, eat, shop, and experience Southern Vermont at VermontBeginsHere.com.