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Day Tripping in Southern Vermont

A self-guided tour, suggested by Pownal resident Katie Schmidt, with photographs by Leslie Morganthal.

Just north of Williamstown, Route 7 crosses the Vermont border into a corner of the Green Mountains that has fostered its own artistic community for more than a century.

Pownal and views

  • Heading north on Route 7, you will cross into Pownal, Vermont.
  • (For a side trip, follow Route 346 into New York and Route 22 north to Cambridge, N.Y., a small town with arts and music, the Hubbard Hall theater and locally made doughnuts on Saturdays.)
  • In Pownal, on Route 7 north of 346, a detour to the right onto Burrington Road (old Route 7) gives a spectacular view of the Taconic range. Pownal has a ‘Popper’ to rival the Hopper, the high valley on Mount Greylock.

  • Burrington Road rejoins Route 7 heading north past hops fields and the Apple Barn, open spring to fall with pick-your-own berries and in season, apples in the fall, aged cheddar cheese and a bakery known for its cider donuts.

Downtown Bennington

  • Route 7 and Route 9 meet at the center of town, with small shops and galleries, Oldcastle Theatre‘s plays, music and film, and live music and fresh coffee at the South Street Cafe.

  • On Route 9 a couple of blocks west, Hemmings, the world’s largest collector car marketplace, has its headquarters in an old-fashioned Sunoco Station, with a cafe and museum. Hemmings also holds Cruise-Ins, informal car shows, twice a month, May through August.

  • On Route 7 at the north end of town, the Blue Benn draws locals in an old-fashioned diner with a jukebox and specials on the walls – chicken croquettes, pancakes, omelettes …
  • Just off Route 7, Bennington Potters have been making stoneware for more than 70 years. Visit the shop or take a tour to see the potters at work.

  • On Route 9 east, the Bennington Bookshop is a quiet spot to check out local writers.
  • Heading east past the shops and uphill, you’ll find the warm red building of Bakkerij Krijnen, a Dutch Bakery that offers bread, pastries, cookies, waffles with caramel, and light lunch: soups and quiche, coffee and hot chocolate.

Route 9 West and Old Bennington

  • From the center of town, head west on Route 9, and the stone facade of the Bennington Museum will appear on the left. The museum focuses on regional artists from Rockwell Kent to New Yorker cartoonist Ed Koren and local history and the largest collection of Grandma Moses paintings in the world.

  • Just past the museum, a right onto Monument Ave. will take you to the tower on the horizon – the Bennington Battle Monument, a 306-foot-tall salute to the Revolutionary War, open from mid-April to Oct. 31, with historic events in spring and summer.
  • At the corner of Monument Ave. and Route 9 stands the Old First Church built in 1806, where the poet Robert Frost is buried. He lived and wrote some of his best-known work on a farm nearby.
  • You are now in the National Historic District of Old Bennington, the original center of town, founded in 1761. It is now an incorporated village of historic clapboard houses, historic markers and buildings like the Walloomsac Inn (1764), the Jedediah Dewey House (1764) and the Burying Ground.

  • Continuing west on Route 9, you will come to Camelot Village, a collection of shops and dealers of antiques and collectibles, and the site of community events including the Southern Vermont Arts and Crafts Festival as part of Bennington Arts Weekend in August and the annual Garlic and Herb Festival in September.
  • Cross into New York State, where Vermont Route 9 becomes New York Route 7, and dip into Hoosick, N.Y., to stop at the Big Moose Deli, a local curiosity with an eclectic selection of foods and gifts and ton of hot sauces too, run by a group of combat veterans who have come home.

North Bennington …

  • From downtown Bennington on Route 7, take the first exit and follow 67 north to Bennington College. Founded in the 1930s, this liberal arts college with a campus of classic New England buildings hosts concerts, performances and talks, and exhibits with visiting artists, and its well-known MFA program holds a week of readings by nationally known visiting writers in January and June.

  • Keep on Route 67 north to the village of North Bennington, where the historic Park McCullough House opens its grounds and gardens as a public park and hosts concerts and performances.
  • The North Bennington Outdoor Sculpture Show curates an annual exhibit near the 1880s railway station. Powers Market, the general store, offers hot and cold drinks, hot and cold sandwiches and desserts. And Lake Paran lies northeast of town.
  • Heading west out of town on Mercantile Street and Overlea Road will bring you to Route 7A, and (heading briefly north) to the Robert Frost Stone House in Shaftsbury. Frost lived here when he won the first of four Pulitzer Prizes and wrote Stopping by Woods on a Snowy Evening. The museum is now run by Bennington College and hosts readings and concerts.
  • While you’re in Shaftsbury, head north up Route 7A to crown the trip with a stop at the Chocolate Barn, known for their homemade ice cream – wild honey vanilla, coffee fudge swirl, pecan caramel praline, and cranberry. They make their own chocolates and keep a collection of antique chocolate molds.
  • Across the street, Clear Brook Farm runs a plant nursery and farm store for their own plants and produce and local cheese, honey, yogurt, meats, baked goods and more.

… and points north

  • Continuing up Route 7A through Sunderland will bring you to the Skyline Drive up Mount Equinox, the longest privately-owned toll road in the U.S. (and the toll still exists). It’s a 5-mile climb up 3,248 feet. On clear days you can see Canada. You can also see a film on the lives of Cartusian monks and visit the meditation / prayer chapel. Hiking trails lead to the sculpture park at the Southern Vermont Arts Center, where regional contemporary artists display work in solo, juried and group shows.

  • Just off Route 7A on the way into Manchester lies Hildene, the historic home of Robert Todd Lincoln, son of Abraham Lincoln. Along with the house and gardens known for their tree peonies, the museum looks closely into the president’s life and death and into his son’s. It also maintains 412 acres with trails, a working goat farm and dairy and a pollinator sanctuary.
  • Continue on into Manchester to visit the outlet stores or the artisan galleries or take in a visiting writer at Northshire Bookstore. And a quick jog to Dorset will bring in the Dorset Theatre Festival and performances by artists in residence at the Marble House.

East of Bennington and home

  • Route 9, also known as the Molly Stark Trail, runs east from Bennington into Woodford, Vt., where you’ll find a scenic overlook and Woodford State Park, a good place for snowshoeing and beaver dams.

  • Just off Route 9, Prospect Mountain offers cross country and Nordic skiing in the winter with back-country trails and a comfortable lodge with homemade food.
  • You can loop back to North Adams on Route 8 through Stamford, Vt., or continue east on Route 9 to Wilmington, a classic Vermont town alive with arts, antiques, galleries and local restaurants like Dot’s of Vermont and Jezebel’s Eatery in the 1836 Lyman House.
  • Bennington to Wilmington makes a beautiful drive during the fall foliage season, and you can make an even bigger loop back to North Adams from here; take Route 100 through Whitingham and Readsboro, past the Readsboro Glassworks, to pick up Route 8 south and come home.
Bennington and surrounding areas