Trace the route that Revolutionary War General John Stark took after he vowed to defeat the British at the Battle of Bennington, “or this night Molly Stark sleeps a widow, he's said to have declared.” —Peter Crabtree
Sam's Outdoor Outfitters, Brattleboro: Begin your journey with a visit to Sam's, an anchor store for Brattleboro's red-brick downtown since 1932. You'll find all you might require for a camping stay in the Green Mountain National Forest, such as Vermont-made Darn Tough socks. Help yourself to free popcorn, a Sam's tradition. 802-254-2933; samsoutfitters.com.
TJ Buckley's, Brattleboro: Set in a restored 1925 Worcester Dining Car, this restaurant wins rave reviews not only for its food—scallops and rabbit might appear on the menu—but also for its wine list, atmosphere, and service. Reservations are recommended. 802-257-4922; tjbuckleysuptowndining.com.
Marlboro Music Festival, Marlboro: Each year from mid-July to mid-August, a select group of classical musicians gathers to perform chamber works. World-renowned artists play alongside up-and-coming instrumentalists and singers in Marlboro College's intimate Persons Auditorium. 215-569-4690; marlboromusic.org.
Hogback Mountain Scenic Overlook, Wilmington: Is that Massachusetts and New Hampshire you see? Well, yes, because on a clear day there's a 100-mile view from the base of this former ski area. Stop in at the gift shop and pick up some Vermont maple syrup and cheddar. 800-427-5494; hogbackgifts.com.
Harriman Reservoir, Wilmington: While floating on your back in the cool, clear water of the reservoir, also known as Lake Whitingham, keep an eye open for bald eagles. Or rent a pontoon boat, personal watercraft, or stand-up paddleboard, and explore 28 miles of coastline. 802-464-2108; highcountrymarine.com.
Hemmings Motor News, Bennington: Hemmings bills itself as the collector car hobbyist's bible, and pilgrims drive for miles to attend the Thursday night cruise-ins the magazine hosts in summertime. Stop by Hemmings' Sunoco Filling Station (802-447-9580) and have an attendant check your oil as you visit the adjoining antique car museum and filling station. 802-447-9652; hemmings.com.
Bennington Museum, Bennington: The museum has long been known for having one of the world's largest public collections of Grandma Moses paintings. The Bennington Modernism gallery focuses on the work of abstract artists associated with Bennington College from the 1950s through the 1970s. 802-447-1571; benningtonmuseum.org.
Old First Church, Old Bennington: The soaring white clapboard bell tower of this New England classic overlooks the graveyard where poet Robert Frost is buried. Visitors pay tribute to the American master by leaving coins and tokens on his gravestone, which bears the inscription “I had a lover's quarrel with the world.” From there, it's just a short walk to the 306-foot-tall obelisk that commemorates the 1777 Battle of Bennington. 802-447-1223; oldfirstchurchbenn.org; benningtonbattlemonument.com.