Fall is one of the most magical times of the year to visit Bennington, Vermont. There is just something about the crisp, cool days, the crunchy leaves underfoot, and the smell of wood smoke wafting through the town. We want you to love autumn in Bennington as much as we do, so we’re sharing our favorite fall activities around town.
Celebrate the Harvest Season in Bennington
The bounty of harvest season provides lots of opportunities to enjoy the local flavors of fall. Here are some ideas for enjoying farm-fresh food and celebrating the harvest.
Pick Apples at a Local Orchard
Apple picking is a quintessential fall activity and a fun family outing for all ages. Terry’s Orchard is a family-owned and operated orchard in Bennington, Vermont that is open for pick-your-own apples during the late summer and fall. Varieties include McIntosh, Cortland, Empire, Liberty, Northern Spy, Red Max, Spencer, and more. Be sure to stop in the orchard store from some fresh cider and maple syrup.
Visit the Bennington Farmers’ Market
The Bennington Farmers’ Market is a year-round showcase of local farm products, including fresh meats, veggies, cheeses, baked goods, maple syrup, honey, and crafts. Visit the market every Saturday through the end of October from 10-1 in Riverwalk Park at 150 Depot Street in Bennington. The market features live music every Saturday and special events throughout the season. It’s a great place to connect with locals, enjoy some goodies, and find one-of-a-kind Vermont gifts.
Come to Bennington for Oktoberfest
The 2019 Norshaft Lions Oktoberfest will take place on October 5 from 11 am – 5 pm at Colgate Park in Bennington. In addition to great beer, visitors will enjoy a wide variety of ethnic foods, live music by the Rymanowski Brothers, wagon rides, and lots of family-friendly activities. Not only is Colgate Park a beautiful spot for a fall festival, but all of the proceeds raised from the event support local causes and charities.
Check out Fallapalooza in Downtown Bennington
Every year at the end of October, downtown Bennington closes down Main Street for a last celebration of fall. Bring the kids for downtown trick-or-treating, pumpkin carving and decorating, medieval combat demonstrations, live entertainment, and craft and food vendors. Fallapalooza 2019 will take place on October 26, from 11 am – 3 pm.
Get Outside in Bennington, Vermont
Fall is one of the best times to enjoy the outdoors in and around Bennington, Vermont. Our parks, back roads, and waterways are alive with color and just begging to be explored. Here are some ideas for getting outside in Bennington.
Go for a Hike
Lace-up your hiking boots and enjoy those colorful leaves first-hand. We’ve got some great ideas for easy fall hiking, or you can check out our recreation page for even more ideas. Wherever your boots take you, be sure to pack your camera.
Discover Bennington’s Covered Bridges
Bennington County is home to five beautiful covered bridges, and you’ll find three of them right here in the towns of Bennington and North Bennington. All of the Bennington covered bridges cross the Walloomsac River, and they are all within a mile of each other, so you can visit them all in a very short period of time.
Local tip: The Walloomsac River is a fabulous trout stream, and according to the Vermont Fish & Wildlife Department, much of it can be fished year-round.
Here’s a brief overview of the three covered bridges in Bennington and North Bennington, Vermont:
- Silk Covered Bridge – The Silk Covered Bridge crosses the Walloomsac on Silk Road, not far from its intersection with Route 67A in Bennington. This is a Town lattice truss bridge, built in 1840 and added to the National Register of Historic Places in 1973.
- Paper Mill Village Bridge – The Paper Mill Village Bridge is another Town lattice truss bridge that carries Murphy Road across the Walloomsac River near its junction with Route 67A in Bennington. It was constructed in 1889 and added to the National Register of Historic Places in 1973.
- Burt Henry Covered Bridge – The Henry Covered Bridge is located on River Road in North Bennington. Another Town lattice truss bridge, it was originally built in 1840 and rebuilt in 1989. The Henry Covered Bridge was added to the National Register of Historic Places in 1973. There is a small parking and picnic area near the Henry Bridge. Be sure to visit North Bennington’s edible forest garden in McWaters Park, which is adjacent to the parking area.
Go to a Play at Oldcastle Theatre
Bennington’s downtown theatre company has been producing professional productions since 1972. Located on Main Street in the heart of downtown, Oldcastle’s line-up features comedies, musicals, and dramas in an intimate setting.
This October, Oldcastle will be performing an original play written and directed by Oldcastle’s Producing Artistic Director, Eric Peterson, entitled Water, Water Everywhere… The play is set in the fictional town of Walloomsac, Vermont, and focuses on the complications that arise when the town realizes that a local factory has been spewing Perfluorootaonic acid (PFOA) and contaminating groundwater and soil.
Water, Water, Everywhere… will run from October 4 – October 20, 2019. Find out more and purchase your tickets at Oldcastle Theatre.
Psst… Looking for ideas for dinner before heading to the theatre? The following restaurants offer discounts to patrons who present their theatre tickets to their servers.
- Kevin’s Sports Pub and Restaurant: Free Dessert with ticket and the purchase of a menu item
- Mount Anthony Country Club: 10% off your bill with ticket
- Madison Brewing Company: 10% off your bill with ticket
Tour a Historic Home
Get a taste of Bennington history during your visit. The beautiful Victorian-era Park McCullough House was built in 1864 – 1865 by attorney and entrepreneur Trenor Park, and is considered on the finest and best-preserved Victorian mansions in New England. You can visit this beauty, the working farm behind it, and the lovely, Mile-Around-the-Woods hiking trail all in one afternoon. Park McCullough House is located in the village of North Bennington and is open for tours on weekends until the end of the fall foliage season. Admission is $15 per person.
For history on a smaller scale, check out the Robert Frost Stone House Museum on Route 7A in Shaftsbury, Vermont. This literary landmark was home to poet Robert Frost from 1920 – 1929, which was a prolific time period of his writing career. He composed many of his most famous works here, including “Stopping by Woods on a Snowy Evening,” which was written on a hot June morning at his dining room table. The Robert Frost House is open from Wednesday – Sunday, 10 am – 4 pm, until the end of October.
Fall is one of the most beautiful seasons to visit the historic town of Bennington, Vermont. Whether you visit for an afternoon or a whole week, you’ll find plenty to do beyond leaf-peeping.
- Activities & Adventures
- Art, History, Theatre
- Events & Festivals
- Fall Foliage
- Outdoor Recreation
- Tour Guides & Itineraries