Day Trips: Journeys and Jaunts in the Bennington Region

If you’ve seen our slideshow, checked out our events calendar, or visited campus, you know that Bennington College has a thriving on-campus culture: concerts, exhibitions, plays, parties, outdoor activities, and more.

But the region around Bennington also offers plenty of diversion—with a lot of good eats, stunning views, and serious bargains along the way. To help you explore the nexus of the Berkshires, Taconics, and Green Mountains, we’ve put together four itineraries. The first two appear this week, and the rest will appear next week in Part 2 of this series. (To be honest, attempting even one of these itineraries in a single day might be crazy—there’s enough here for several months’ worth of weekend day trips—but we’ll cheer you on in the attempt!)

This sampling of what the area has to offer is meant to inspire you as much as to guide you. If you take a detour and come upon a hidden treasure, tell us about it.

Itineraries:

• Retro Jaunt to Manchester, Vermont
• Autumnal Meander through the Mists of Old Bennington

Retro Jaunt to Manchester, Vermont

This trip is nostalgic—think 1950s touristy—with a few twists. You start at a traditional-looking diner that serves vegetarian food and wind up at a mom-and-pop bookstore that weds knotty pine walls with a killer book selection and coffee shop. Every night thereafter, you’ll eye that Norman Rockwell snow globe on your dresser, think of this marvelous day, and wish you hadn’t finished off all the maple candy.

Breakfast at the Blue Benn Diner in Bennington. This is an original “Silk City” diner from 1949, and although they offer a vast vegetarian selection, they are unpretentious and open to every substitution imaginable. Yes, it’s a greasy spoon! And it’s popular, so come early. Bring cash; they don’t take any plastic.

Drive north on Vermont Route 7A. On this road, which runs parallel to the highway we call “Super 7” and will take you to Manchester, VT, there are lots of mid-century-type tourist motels, cottage rentals, and souvenir shops.

Munchies, Memories, and Mountains. Along Route 7A, check out the sundry roadside crafters, the apple orchards, Clear Brook Farm Stand (open through mid-October), the Chocolate Barn, the Cheese House, and the Norman Rockwell Exhibit at the Arlington Gallery. If this isn’t enough to make you feel like you’re cruising in the “way back” of a station wagon full of extended family, take a drive up Mount Equinox ($7 per car and driver, $2 per passenger) for the vista.

Park in downtown Manchester. It’s good to choose a spot near the junction of Route 7A and Route 11 so you can tour the shops on both of these roads as well as take a gander at the Battenkill River (benches provided!). We recommend the free parking between Hand Motors and the Northshire Bookstore. From here you can walk to everything that follows.

Lunch at Zoey’s Deli, where you can order a sandwich with homemade bread and a side of their signature potato chips; or at Spiral Press Café at the Northshire Bookstore, where you order a specialty coffee and a delicious pastry for dessert.

Afternoon activities:

• Shop. If you're the outdoorsy type, chances are you’ll want to check out the outdoor clothing and gear shop The Mountain Goat. And if you’re an outlet junkie, yes, you will find a Banana Republic and J. Crew. But regardless of what you’re looking for, you shouldn’t pass Lindt without at least buying your roommate a dark chocolate truffle.
• Read and browse books, CDs, and novelties at the Northshire Bookstore. Named Bookseller of the Year by Publishers Weekly, the Northshire is a sprawling converted house with a knotty-pine interior, a terrific selection of classics, bestsellers, new age-y stuff, and magazines (including some foreign ones). If they don’t have it, they’ll order it. There’s wi-fi in the café, but you can only get the password for it by buying a bite to eat.
• Eat dinner at The Bean. This is an affordable Mexican eatery located between the historic district of Manchester and the commercial “hub.” It offers vegetarian options. Candeleros is another fantastic option for Mexican food in Manchester, with slightly higher prices but a great atmosphere and fabulous fare they call "VT-Mex."

Autumnal Meander through the Mists of Old Bennington

This itinerary is perfect for a brisk, fall day. You’ll be surprised at how atmospheric the town of Bennington is, and how rich with history. Okay, so the Battle of Bennington actually took place in New York, but the Green Mountain Boys really earned their gigantic monument (which was built before the one on Bunker Hill, FYI!). Wear your hooded cloak.

Breakfast at Alldays & Onions. Located on Main Street in Bennington, this restaurant uses locally grown produce and serves a tasty brunch that includes a free basket of warm scones.

History to Explore, Curios to Browse:

Visit the Bennington Museum. Drive from Alldays on Route 9 west toward New York, and you’ll see the stately, pillared Bennington Museum on the left. It boasts the largest collection of Grandma Moses art available to the public as well as antique toys, maps, and military artifacts.

Tour the Old First Church. Just up from the museum lies Vermont’s first Protestant church. The founder of Bennington College, Vincent Ravi Booth, was the pastor of this church, and in its graveyard lie the remains of Robert Frost.

Go up the Bennington Battle Monument. For $2, you can take an elevator up the tallest building in Vermont, created to commemorate the Revolutionary War Battle of Bennington. At the top, look north and you’ll see the Bennington campus. The gift shop sells great tchotchkes and beautiful vintage postcards.

Shop at Camelot Village. On the western edge of Old Bennington is a collection of red barns housing shops that sell antiques (victrolas, anyone?), flowers, fudge, and handmade pottery, jewelry, and glass.

Tour the Southern Vermont College mansion. At one of the two other colleges in Bennington is a beautiful mansion, complete with a wishing well. The building is open to the public, so you can just drive on up. Behind the mansion, you’ll find a trail punctuated by beautiful statues. On Halloween night, a community fete is held on the premises that includes a haunted house.

Lunch at Izabella’s Eatery in downtown Bennington. In this clean, sunny café you can order a goat cheese and chutney sandwich or a mini quiche…in other words, have a scrumptious repast. Another great option is the South Street Café around the corner, where you can lounge on the velvet couch to nibble your bagel.

Afternoon whimsy:

• Get your thrift fix at the Salvation Army, located on Route 7 as you drive south toward Massachusetts. Consider trading in that tee-shirt from summer camp. Or buying someone else’s.

• Wander through the pumpkin patch at the Apple Barn. The Apple Barn will answer your every autumn yen: for cider donuts, jack-o-lanterns, scented candles, gourds, pies, and even—yes—a pumpkin patch.

"Autumnal Meander" Detour:

If you prefer to view the dazzling foliage from the trail instead of the road, skip the historic sites and the shopping and hike the Appalachian Trail, which crosses Route 9 (a.k.a Main Street) just a few miles east of Bennington. You can park at the trailhead and follow the AT southwest to the Harmon Hill summit, which offers picturesque view of Bennington, Mt. Anthony, and the Bennington Monument. You should allow 3-4 hours to reach the summit and back, but the hike is a fairly moderate one, save for a stretch of steep rock and log steps at the start.

More:

• Housing at Bennington: A Four-Part Series
• Bennington's Music Scene
• Bodies in Motion: Athletics, Fitness, and the Great Outdoors at Bennington

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