By far the largest Vermont town south of Burlington, Bennington (pop. 16,451) is a bustling little manufacturing and commercial center. It was the site of a significant victory against the British-paid Hessians in 1777 during the American Revolution, a sweet morale-booster that contributed to the defeat of General “Gentleman Johnny” Burgoyne’s army of Redcoats at Saratoga. In the subsequent centuries, Bennington’s name became synonymous with art: the decorative arts of the antebellum United States Pottery Company; the liberal arts of Bennington College, one of the nation’s most expensive and exclusive private colleges; and the folk art of Mary Robertson “Grandma” Moses.
The largest public collection of Grandma Moses’s beguiling work is on display in the Bennington Museum (closed Wed.; $8), whose white-columned, ivy-covered edifice is found up the hill on West Main Street (Route 9) in the graceful old part of town. Along with 30 Grandma Moses paintings and the rural schoolhouse she attended two centuries ago, the museum also has a wide variety of historical artifacts, examples of early Bennington pottery, and the sole survivor of the fabulous motor cars once made here in Bennington: a 1925 Wasp.
From the Bennington Museum, walk north toward the 306-foot obelisk that towers over the town: the Bennington Battle Monument, erected in 1891 to commemorate the Revolutionary War victory, which actually occurred west of town, over the New York border. For $2, mid-April–November 1, an elevator will take you to an observation room near the top of the tower for a great view up and down the valley.
Bennington is also the final resting place of poet Robert Frost, whose tombstone in the burial ground alongside the Old First Church, at Church and Monument Streets, says: “I had a lover’s quarrel with the world.”
If anyone starts erecting monuments to good dining instead of old wars or dead poets, this town would have another tower of stone beside the Blue Benn Diner (802/442-5140), north of town at 314 North Street. The fact that it’s a vintage 1940s Silk City certainly gives this cozy, nonsmoking joint character. But what earns the seven-days-a-week (from 6 am) loyalty of its patrons is the top-notch short-order cooking: From baked meat loaf and roast pork to broccoli stir-fry and multigrain pancakes, the food’s good, cheap, and served up so fast you’ll barely have time to choose your song on the wall-hung jukebox at your table.
Most of Bennington’s accommodations are strung along Route 7A to the north and US-7 to the south of downtown, all local names but for the Ramada and Best Western inns found on 7A. If you are in the market for a distinctive B&B, check out the central and historic Four Chimneys Inn ($135 and up; 802/447-3500), on Route 9 at 21 West Road.
