One of the nicest things about Brattleboro is the way that the town center hugs the Connecticut River, nestled at the foot of Mount Wantastiquet. Mount Wantastiquet, being across the river, is in New Hampshire, and is a great place to hike without a long drive to get there. The trail head is just a ten minute drive from the Chesterfield Inn.
I often meet a friend there for a quick hike in the summer or fall (the trail is generally too wet in the spring with the snow melt rushing down the mountain. ) We meet at the bottom of the mountain , just behind the Hinsdale Walmart, where there is a small parking area. From Main Street in Brattleboro, go over the bridge to Hinsdale and take the first left on Mountain Road, a dirt road that ends at the parking area. Depending on your pace, you can get up and down Wantastiquet in less than 2 hours.
The trail follows switchbacks that start to climb immediately. There is a stream that cascades down the side of the mountain, so you can hear rushing water all the way up. The trail, an old quarry road, is wide enough for mountain bikers and is about 2 miles long. Just when you think you’ve had enough, the trail levels out along the ridge of the mountain, and you’ll see a short detour that leads to a rock outcropping with a small monument and an expansive view of the Connecticut River Valley, the town of Brattleboro and the Green Mountains in the distance. You see the ski areas Mount Snow, Stratton , and Bromley, as well as the rolling hills of Massachusetts to the south. The trail continues on to Mine Ledge, to the Madame Sherri Forest and then to Pisgah Park, but we usually stop to look at the view and then head down, back the way we came.