9 Reasons To Head To Bennington

In May, some Vermonters head south, but you don’t have to go too far south to get away. Nestled in the southwestern corner of the state, Bennington is bustling this month with a point-to-point marathon on May 21. On May 27, it’s also the site of a block party/crafts fair and on May 20 serves as a base camp for the largest pro/am bike race/tour in the country, the Tour of the Battenkill, just across the New York border.

After a run or ride, grab a member-brewed beer at the state’s first beer co-op, paddle Vermont’s wildest lake, stay at B&B that serves guests free martinis, visit one of the area’s many museums. Pack the bikes, running shoes, fly-rods and hiking boots. Sunscreen is optional.


With its old stone buildings, country farmhouses and three historic districts (Old Bennington, Bennington Downtown, and North Bennington), Bennington lives up to its slogan “Vermont Begins Here.” Chartered in 1749, Bennington constantly reminds you of its history with its restored brick storefronts and classic colonials. The 306-foot tall Bennington Monument commemorates the Battle of Bennington and, on Sept. 9, plays host to the American Lung Association’s Fight for Air Climb, a race up the monument’s spiral steps. When you’ve taken in the view from the top, stroll down to the Bennington Museum to see the largest collection of paintings by Grandma Moses. Then stop by the First Church cemetery to pay homage to poet Robert Frost whose headstone there reads “I had a lover’s quarrel with the world.”

If you care to pick up the pace, run through five of Bennington County’s villages in one shot. After a one-year hiatus, the Shires of Vermont marathon is back and slated for May 21. The USATF-sanctioned race starts at Bennington College and sends runners on back roads through the villages of North Bennington, Shaftsbury, Arlington, and Sunderland to Manchester. There’s a net elevation gain of 1,500 feet, so don’t expect a PR, but it is a Boston Marathon qualifier and the scenery can’t be beat. Buses shuttle from the finish in Manchester’s Hunter Park to the start. www.bkvr.net/shires-of-vermont-marathon. For a shorter race, sign up for the Annual Steve Zemianek Bennington Road Race – a 3.8 mile and 10K race on May 7. If you’re in town and want to join in a group run, the Batten Kill Valley Runners (www.bkvr.net) hosts weekly runs around the county.

The Tour de Battenkill, photo by David Kraus
The Tour de Battenkill, photo by David Kraus

On May 19-20, some 3,000 cyclists are expected to take part in what’s billed as the largest pro/am race/ride in America: the Tour of the Battenkill. The Tour starts May 20 in Greenwich, NY, 20 miles northwest of Bennington. It sends 250 pro racers (and seeded amateurs) out on a mass start on a 75-mile loop on back roads, through covered bridges and across hilly farmland. There are sections on dirt roads and 39/25 gearing is recommended. Once the pros head out, a mass start sends everyone else on a gran fondo tour, with aid stations along the way and an option for a 26-mile loop. The weekend also features a giant bike Expo at the Washington Valley Fairgrounds. On June 3, pros return for the UCI America’s Pro Invitational on a similar, 100K course. www.tourofthebattenkill.com


For a more leisurely ride on your own timeline or pace, there are plenty of great routes on the Vermont side of the border. “We are in a corner so a lot of your rides end up being in three states and can be rolling, or challenging with hill climbs,” says Peter Hall of Highlander Bicycle, located in the historic Holden-Leonard Mill complex. From the shop, an easy 14-mile “Covered Bridge Ride” goes past the Old First Church and Cemetery, the Walloomsac Inn, the Catamount Tavern statue, and the Bennington Battle Monument. The ride crosses the Walloomsac on three covered bridges: the Silk Road Bridge, the Paper Mill Bridge, and the Burt Henry Bridge, all within two miles of each other. The Spirits of Old Bennington Distillery is visible from the Paper Mill Bridge, so stop in for a tasting. The shop also lists a number of challenging rides at www.Hbike.com/local-rides/. Or, visit Battenkill Bicycles in Manchester for more local knowledge and group rides. www.battenkillbicycles.com


On May 6, The Bennington Area Trail System (BATS), one of the newer chapters of the Vermont Mountain Bike Association, hosts its second annual Trail Mix event. It kicks off at noon at the Everett Mansion at Southern Vermont College with group rides on about 10 miles of singletrack and other multiuse trails. Catch a talk by local Olympic Nordic ski racer Andy Newell, demo Salomon footwear and sample from food trucks and Spirits of Old Bennington. For trail beta and event updates, visit BATSvt.org or the BATSvt Facebook page.


With the rolling Green Mountains to the east and the short, steep Taconic Peaks to the west there is no shortage of good hikes in the Bennington area. There’s even one that lets you access a National Forest from a sidewalk downtown. Bald Mountain’s North Branch Street trailhead will have a new parking lot and Forest Service kiosk marking the downtown trailhead by late spring. The Bald Mountain Trail, known by locals as “The White Rocks,” is 2.6 miles to the White Rocks, and another mile to the krummholz and scrub of the summit. There, you have views to the Taconics and the Hudson Valley. To the north is Glastenbury Wilderness—a gem in its own right.

Not far from Bennington, the Appalachian National Scenic Trail and the Long Trail (AT/LT) coincide, letting you hike sections of both. The trailhead is on Route 9 which is exactly 5 miles east from the Four Corners in Bennington. The out-and-back hike to Harmon Hill on the AT/LT heads south, steeply ascending a series of rock steps before easing up for the remainder of the hike. It later opens up in a grassy meadow—Harmon Hill—with views of Bennington and the Taconics.


Vermont’s state parks open on Memorial Day and if you reserve ahead, you can rent a 3-bedroom cottage on the water at Lake Shaftsbury State Park for just $80 a night. The 84-acre park also has 15 lean-to sites, a nature trail, paddling and picnic areas. For a larger park, head to the hills: at an elevation of 2,400 ft., set on a mountain plateau on the shore of Adams Reservoir, Woodford State Park is the highest altitude state park in Vermont. The park has 107 sites for tents and RVs, four rental cabins ($48 a night), and a waterfront with kayak and rowboat rentals. Fish for trout in the reservoir and watch for loon and other wildlife. vtstateparks.com

For a paddle you won’t forget, head east on Route 9 East and take Somerset Road, an easy-to-miss turn at the bottom of a steep grade, to Somerset Reservoir. The largest wild lake in the state is nestled into 200,000 acres of the Green Mountain National Forest. There are no camps or dwellings on its 16 miles of shoreline and camping is prohibited. Loons call across the water and you can explore the lake’s dozen or so islands. Boats are not allowed to go faster than 10 mph. The drive to Somerset is about 25 miles from Bennington and much of Somerset Road (11 miles to Reservoir) is dirt, so plan for at least an hour in the car and get there early to avoid a windy paddle back to the parking put-in. More details, greenmountainconservancy.org

Downtown Bennington's historic streets, cafe and artsy vibe beg you to sit back and relax. Photo by Greg Nesbit
Downtown Bennington’s historic streets, cafe and artsy vibe beg you to sit back and relax. Photo by Greg Nesbit

Opened in 2016, Harvest Brewing is the first brewery co-op in Vermont and features a hand-picked selection of craft beer and limited edition member/owner brews. With a speak-easy atmosphere blended with local art, lava lamps and a constant rotation of vintage vinyl on the turntable—you should check it out (VMBA-member discount available). The brewery often hosts bands, open mics, and other event. It is a good place to stop and find out what else is going on in town that evening. Another great spot downtown is Madison’s Brewery, a fixture on Main Street that serves lunch and dinner as well as their own craft beer, now also available in cans.

For dinner without the kids, try Pangea Lounge in North Bennington or Allegro in downtown Bennington. The Publyk House provides a deck with a view and tasteful menus. Ramuntos Brick Oven Pizza is an all-around favorite for good, quick eats and craft beers. The Taphouse at Catamount Glass has a small menu, good beer, and you can purchase their wares.


If you want a classic Vermont inn right o the BATS trails on Mt. Anthony, The Four Chimneys Inn with its guests-only bar, and extensive gardens will make you feel like you really deserved this vacation. The historic The Henry House Inn, located adjacent to the Henry Bridge is just o the beaten path, yet close to what Bennington area has to o er.

In the village, the Paradise Inn is a convenient walk to downtown (VMBA discount available as is an anglers package with two days of meals, accommodations and trout shing with guide Chris Bates). For breakfast, simply walk across the parking lot to the Brown Cow Café (vegetarian, vegan, and GF options).

A unique twist on the “bed and breakfast” the Sa ord Mills Inn o ers “Accommodations and Aperitifs”—which means included in the price of a stay are complimentary Martinis, wine and beer, accompanied by appetizers and dessert.

A mere mile up 7A north is Harwood Hill, is a classic 1930s motel that’s been renovated by two editors and a filmmaker and features local art, an artist in residence and an Arts Package (discounts at local museums and galleries), all at reasonable prices. The best part is you can take your best friend too—dogs are allowed for an additional $10 per day.


Bennington is an arts town, and one of the best ways to discover its crafts is to head to Mayfest on May 27. More than 120 local artists and craftspeople set up shop downtown with ethnic food pop-ups on Spring Street. Another don’t-miss is Bennington Potters, in the historic Feed Mill off County Street, and if you arrange ahead you can get a tour of the potters in action.

The ever-popular Vermont Arts Exchange Basement Music Series hosts great talent, and Old Castle Theatre productions are go-to’s for a night out in Bennington. The Bennington Chamber website (bennington.com) has a calendar and events page to help you plan, and the Bennington Young Professionals Facebook page posts a list of events, weekly.