A soaring aerial view of Brattleboro can be found atop Wantastiquet Mountain, which is just across the Connecticut River in New Hampshire (figure on a round-trip of about 3 hr.). To reach the base of the "mountain" (a term that's a bit grandiose), cross the river on the two green steel bridges, then turn left on the first dirt road; go 1/5 mile to a parking area on your right. The trail begins here via a carriage road (stick to the main trail and avoid the side trails) winding about 2 miles through a forest and past open ledges to the summit, which is marked by a monument dating from 1908. From here, you'll be rewarded with sweeping views of the river, town, and landscapes beyond.
The Vermont Canoe Touring Center (tel. 802/257-5008), open seasonally, is at the intersection of Route 5 and the West River north of town. This is a fine spot to rent a canoe or kayak to poke around for a couple of hours, half a day, or a full day. Explore locally, or arrange for a shuttle upriver or down. The owners are helpful about providing information and maps to keep you on track. Among the best spots, especially for birders, are the marshy areas along the lower West River and a detour off the Connecticut River, locally called "the Everglades." Get a lunch to go at the Brattleboro Food Co-op and make a day of it.
Bike rentals and advice on day-trip destinations are available at the Brattleboro Bicycle Shop, 165 Main St. (tel. 800/272-8245 or 802/254-8644; www.bratbike.com). Hybrid bikes ideal for exploring area back roads can be rented by the day or week.