By far the largest Vermont town south of Burlington, Bennington (pop. 15,764) 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 Anna Mary Robertson “Grandma” Moses.
The largest public collection of Grandma Moses’s beguiling work is on display in the Bennington Museum (75 Main St., daily summer, Thurs.-Tues. Sept.-Dec. and Feb.-Apr., $10 adults), found up the hill on Route 9 in the graceful old part of town. Along with 25 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, completed in 1891 to commemorate the Revolutionary War victory, which actually occurred west of town, over the New York state border. An elevator (mid-Apr.-Oct., $5) takes 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, in the burial ground alongside the Old First Church, at Church Lane and Monument Avenue. His tombstone reads, “I had a lover’s quarrel with the world.”
Whether or not you need gas, those interested in old cars and automobilia will want to stop by the full-service recreated Sunoco filling station and antique car collection at Hemmings Motor News (222 Main St., 802/447-9580).
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 (314 North St., 802/442-5140, Mon.-Sat. from 6am, Sun. from 7am), on a bend in US-7 north of town. 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 loyalty of its patrons is the top-notch short-order cooking: From baked meat loaf and roast beef to broccoli stir-fry and multigrain pancakes, the food is 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 Best Western inn found on Route 7A, and the Hampton Inn on Hannaford Square. If you are in the market for a distinctive B&B, check out the central, historic, and highly regarded Four Chimneys Inn (21 West Rd., 802/447-3500, $129 and up), which offers 11 rooms and 11 acres of grounds and gardens, and a full breakfast for overnight guests, along Route 9.