"Just to warn you: It's as steep as a cow's nose!" said the hiker we encountered at the trailhead for Harmon Hill. We soon found out what that meant, on a 1.8-mile trail that went straight up for the first quarter-mile (rather a big cow, we'd say), and then traversed a ridge with lofty views of Bennington. That, and the scenic drive along the Molly Stark Trail from Brattleboro, is a great introduction to Bennington, Vt. Whether you visit as part of a college tour (there are five schools here) or on a fall color drive, take some time to discover this historic town of 16,000. It's especially lovely in autumn, when a late-season trip to the top of 306-foot-tall Bennington Battle Monument offers an overview of heathery orange valleys. This time of year, the cider at the Apple Barn and Country Bake Shop tastes especially sweet. Plus, you can get a jump on holiday shopping, if you're so motivated, at Bennington Potters or one of the local galleries. Pack hiking boots, because you're likely to be tempted by one of the many trailheads here, including Vermont's Long Trail and a section of the Appalachian Trail. Just beware if someone uses the term "cow's nose" to describe a trail.
There's a motel just outside of town with a sign that boasts "color TV," but you might be more tempted by the circa 1857 Eddington House Inn (21 Main St., 800-941-1857, www.eddingtonhouseinn.com, from $139; midweek college visit rate $109, November to mid-May) in North Bennington Village, named "best small B&B in Vermont" by Yankee magazine this year. Located within walking distance to town, restaurants, and short hikes, this beautiful home takes the "breakfast" part seriously, with stuffed French toast and fresh fruit in the morning. Cozy Vermont charm awaits guests at the Georgian Revival-style Four Chimneys Inn & Restaurant (21 West Road, 802-447-3500, www.fourchimneys.com, from $149) where 11 guest rooms are set in the main house, the original ice house (with a loft) and a carriage house. All rooms are unique; some have gas- or wood-burning fireplaces and four-poster beds. If an indoor pool is a must after a day touring colleges or sightseeing, consider the 80-room Hampton Inn Bennington (51 Hannaford Square, 855-271-3622, www.hamptoninn.com, from $159). There's a small fitness center on the property, and rates include breakfast.
The landmark Blue Benn Diner (318 North St., 802-442-5140, most prices $5.95 and up, cash only) is an old Silk City dining car made in New Jersey in the 1940s. True to form, it's made of stainless steel with a barreled ceiling, vinyl booths, and a dining counter, and breakfast is served all day. You'll get a decent meal if you don't stray too far from tried-and-true diner fare, like a stack of fluffy pancakes. Another non-fancy option — good for those who've spent the morning on a hiking trail — is Lil' Britain (116 North St., 802-442-2447, www.lilbritainfishandchips.com, from $7), a real Brit-owned chippy place. It's kind of basic inside, with a few tables, plus a replica phone booth and a display of British treats (like Malteasers) available for purchase. But the food is spot on: fresh haddock cooked in batter, crispy and light, plus bangers and mash, steak and kidney pie, and tasty fish tacos with Baja slaw, a bargain at 2 for $7. Bennington's best fine dining option, if awards are an indication, is Pangaea (1 Prospect St., North Bennington, 802-442-7171, www.vermontfinedining.com, from $24) where Chef Bill Scully creates culinary magic worthy of Midtown Manhattan, with a seasonal, three-course tasting menu and more casual lounge dining. A recent starter: Vermont boar and brie Wellington. An in-town bakery and sandwich shop called Crazy Russian Girls (415 Main St., 802-442-4688, from $4), has won a strong following for its freshly baked Irish whiskey cake, maple sugar bagels, and other indulgences. Given the season, a stop at the Apple Barn and Country Bake Shop (604 US Route 7, 802-447-7780, www.theapplebarn.com) seems mandatory. Touristy, yes, but who can resist a warm cider doughnut, fresh cider, and a nice slab of Vermont cheddar to take home — or maybe some venison sausage? If it's gorgeous outside, grab made-in-Vermont supplies for an impromptu picnic at Powers Market (9 Main St., 802-442-6821, www.powersmarket.com ).
DURING THE DAY
You know you're in Vermont when . . . signs along Route 9, the 40-mile-long Molly Stark Trail, read "Cheese and maple syrup ahead." And there's the obligatory view of the mountains; here, the primary peak is Mount Anthony, visible from nearly everyplace. There's even a covered bridge — actually, three of them reachable off Northside Drive. Bennington County is known as the Valley of Vermont, framed by the Green Mountains to the East and the Taconic range to the West, but there's a high point in town worth checking out, the 306-foot-4½-inch Bennington Battle Monument (www.historicsites.vermont.gov, $5 per person, open through October), the tallest structure in Vermont, located at the top of Monument Avenue. Made of blue-gray magnesium limestone, the obelisk was built to commemorate the Battle of Bennington (August 1777), a victory for American independence. The stairs are only open on special occasions so you'll probably take the elevator up to take in the views. To get a sense of Bennington's history, pop into the Bennington Museum (75 Main St., 802-447-1571, www.benningtonmuseum.org, $10), to check out battle memorabilia and weaponry, a circa 1924 Wasp Touring Car, and Vermont's largest public collection of paintings by Grandma Moses. Speaking of art, they've been making American stoneware pottery at Bennington Potters (324 County St., 800-205-8033, www.benningtonpotters.com) for 65 years and counting, and their sprawling complex includes galleries with pottery pieces galore, plus pillows and other decor. In a back building, there's a self-guided tour where you might see potters molding, glazing, or otherwise working with clay. (There's a big pile of red clay that you'll want to get your hands into, but . . . don't.) Still grooving on art? Take a look at the fun, funky finds at Fiddlehead at Four Corners (338 Main St., 802-447-1000, www.getartbehappy.com), set in an old bank building. You can add your doodle to the wall in the graffiti room, formerly the bank vault. Among the most eye-popping pieces here are mosaics made by local high school students, both individually and collectively, and they're for sale. All proceeds go back to their school. Come see what's new at Cake Artisan Gallery (103 South St., 323-363-3321, www.cakegallery.us), and that would be everything, since Bennington native Meike Williams just opened the place in September. Specialties include Williams's handmade precious and semi-precious jewelry, ceramics, and upcycled artwork.
Some consider the automobile a work of art. If that's you, don't miss the Hemmings Auto Museum (216 Main St., 802-447-2496, www.hemmings.com, open May-October, free), a small auto museum featuring vintage vehicles on display. And hiking deserves a second mention, as there are so many great trails to choose from. Favorites include Haystack Mountain Trail and Mount Olga Trail, and the gentle Mill-Around Woods at the McCullough Mansion in North Bennington.
Given that Bennington is a college town, you know there's a microbrewery. At Madison Brewing Co. (428 Main St., 802-442-7397, www.madisonbrewingco.com), they offer eight brews on tap (including the new Galaxy single hop IPA), good food, and the option of sitting outdoors if the weather's fine. Bennington's version of Cheers is Kevin's Sports Pub & Restaurant (27 Main St., North Bennington, 802-442-0122, www.kevinssportspubandrestaurant.com), a burgers-and-beer joint with live music on Friday nights and open mike night on Saturdays — perhaps a local performer or emcee-led karaoke. Oldcastle Theatre is closed for the season, alas, but fall (through April) brings performances from the VAE Basement Music Series (29 Sage Street Mill, North Bennington, 802-442-5549, www.vtartxchange.org, ticket prices vary) sponsored by the Vermont Art Exchange. The basement of this mill building is transformed into a cabaret club, hosting acts by jazz pianist Omar Sosa, musical storyteller Howard Fishman, and other diverse talents.
Bennington is 144 miles northwest of Boston. www.bennington.com.
Diane Bair and Pamela Wright can be reached at bairwright@