We have been assembling this resource to help our guests and other visitors to Brattleboro VT plan their trips. We hope that it is valuable to you.
Canoeing and Kayaking
Vermont Canoe Touring Center
Located just up the road (to the left exiting the driveway) you can take guided tours or rent on your own. (802) 257-5008.
On the local rivers (Connecticut and West) you can catch bass (small and large mouth), pike, pickerel, perch, walleye, yellow perch, white perch, shad, trout (in the spring), bluegill and rock bass. At the Retreat Meadows on Route 30, there is a pull out where you can fish the bank for bass, bluegill, pike, pickerel and perch. For trout, the Whetstone Brook in town and following Route 9 has been known to yield some surprising brookies. The West River along Route 30 provides a picturesque place to wade and fly fish for trout. There are also trout in South Pond off Ames Hill Road (you’ll need to get a license for all fishing).
Brattleboro Country Club
A challenging 18 Hole, 6500 Yd, Par 71 Course with driving range. Head right out of the driveway and stay in the right lane, heading down the hill onto Route 30. From Rt. 30 bear left on Upper Dummerston Road. The course is on the left side. Fees $40 – 70. Club rental available. (802) 254-9864
Sweet Pond State Park
Time: 1 hour
This scenic walk around quiet Sweet Pond offers scenery and wildlife. Turn right out of our driveway. Head through downtown to the intersection at the bottom of the hill and turn right up the hill on Rt.5. Take Rt. 5 south to the Guilford Country Store, turn right on Guilford Center Rd. The road is curvy, be sure you stay on Guilford Center Road! In about 5 miles, bear left after you pass through Guilford Village onto Sweet Pond Rd. Continue 2.5 miles, park is on the left.
Time: 1.5 Hours
This switchback Jeep trail to summit offers beautiful views of Brattleboro and surrounding area. Turn right out of our driveway and head through downtown toward Hinsdale NH. At the bottom of the hill you will reach a crazy intersection, turn left and cross the bridge. Immediately after the second bridge over the Connecticut River turn left to parking area on your right.
Molly Stark State Park
Time: 1.5 hours
Climb to the fire tower on Mt. Olga for a striking 100-mile view. Go right out of our driveway and make a right at the first traffic light onto Route 9. Take Rt. 9 west to Marlboro (about 12 miles). Park entrance is on the left 1 mile from Hogback Gift Shop. Stop at ranger station for specific hikes and directions. Day fee: $3 adults
The closest trail access is about 30 minutes away. Go right out of our driveway and stay right at the 2 lane split intersection“ before the stop sign head right (down the hill) onto Route 30. Take Rt. 30 to East Jamaica and make a left on Rt. 100. From here it’s about 7 miles to Stratton Rd. on your right. Continue 4 miles to trailhead.
Time: 3 – 4 Hours
Spectacular above the tree line hiking. Turn left out of our driveway and drive to the roundabout. Head right, over the bridge on Route 9. Take Rt. 9 through Keene, N.H. and continue on Rt. 101 to Marlborough, N.H., then right on Rt. 124 to Jaffrey. Monadnock State Park is on the left. Fee: $4
Distance: 10 miles
Head right out of the driveway and make a right at the first traffic light onto Route 9. At the West Brattleboro fire station continue west and turn left on Greenleaf St. Bear right onto Abbott Road and continue to the intersection of Ames Hill. Continue up hill and turn left to a beautiful distant view from Moore’s Apple Orchard. Turn left at the next road and bear left again just before the house. The road turns into a trail that will connect to Melchen Road then bear left on the pavement back to West Brattleboro.
Head right out of the driveway and turn right at the first traffic light onto Route 9. From Rt. 9 turn left onto Greenleaf St. Follow the paved road 5.5 miles until the pavement ends. Turn left to the Green River covered bridge and waterfall. Explore the dirt roads of the region or make a 14-mile loop by exiting the bridge to the left. Bear left at the first junction following the Green River and left again across the bridge at the three-mile point. A stiff climb will bring you into the Deer Park wilderness area of Halifax. Another left turn will bring you into quaint Halifax village. Turn left on stage road and left again back to Green River.
Head right out of the driveway and stay in the right lane, heading down the hill onto Route 30. From Rt. 30 take the first left on Cedar St. Park along the road at the base of the ski jump. This dirt road extends to the right of the jump and accesses a variety of trails to explore along the ridge above Brattleboro.
Scenic Rt. 30
Distance: 20 miles
Leave our driveway and bike right past the small park and head to your right down Route 30. Just stay on Route 30 and ride along the West River, it offers valley scenery and level terrain. Turn at Depot Rd. & return.
Scenic Rt. 5
Distance: 20-25 miles
Leave our driveway and make a left. Take Rt. 5 north along moderate hills to Putney to view beautiful farms and mountains. Return the same way. For a more challenging ride, turn right onto School Rd. in Dummerston. This steep climb will bring you back through the longest single span covered bridge in Vermont and onto Rt. 30 which you can take all the way back to Brattleboro. When you reach the Brattleboro Retreat, bear left onto Route 5 North. We will be on your left.
Scenic Rt. 119
Distance: 25 miles
Leave our driveway and head right, through downtown. At the bottom of the hill, head left over the bridge to New Hampshire (Route 119). Take Rt. 119 to Hinsdale, N.H., turn left onto Rt. 63 in Hinsdale village for a sturdy climb and spectacular views. Continue on Rt. 63, bear left at Rt. 9 and left on Rt. 5 to bring you back!
Distance: 35 miles
A scenic, rolling ride through 3 states in the lovely Connecticut River Valley. Head right out of our driveway through Downtown Brattleboro. At the bottom of the hill, head left / straight (on the VT side of the river) onto Route 142. Go south on Rt. 142 until the intersection with Rt. 10 in Bernardston, Mass. Turn left and follow Rt. 10/63 North to Hinsdale NH. In Hinsdale, turn left onto Route 119 and head north. Follow Route 119 across the bridge back into VT (Brattleboro) and turn Right on Main Street. Take Main Street straight up to Inn on Putney Road!
On Harriman Reservoir there are 2 established beach swimming places, but also a place called “The Ledges”. This is a well-known, traditional clothing-optional place which has a large sandy beach and big, flat rocks at the water’s edge. There are some rocks to jump from. Go right from the driveway take RT 9 W. Before you get to Wilmington, go S on RT 100 to the Harriman Reservoir. Go ~0.2 miles, pass Dix Rd on your left and then turn right on to Boyd Hill Rd. Go down this dirt road for about a mile to the parking area for the Jacksonville Picnic Area (there is swimming at the picnic area also). Follow the trail to the right of the picnic area into the woods.
Timber Crib Dam
National Historic Site
A National Historic Site. You can swim above and below the Green River Timber Crib Dam near a beautiful covered bridge (and our friend Joanie’s B&B). Take Route 5 South from Brattleboro to Guilford. When you reach the Guilford Country store, take a right onto Guilford Center Road. Stay on this for 4.7 miles until the pavement ends. Bear right onto Stage Road (some maps refer to this as Jacksonville Stage Road, however, the signpost here reads Stage Road). A sign at this intersection reads “2.5 mi to Green River”. At 2.5 miles, you will see the covered bridge on your left. Bear left down the hill, cross the bridge and take an immediate left onto Green River Road. Park anywhere along this road.
Brattleboro High School
The school just installed 6 new courts, free and open to the public. Turn right out of the driveway and go through downtown, head South on 5. Make a Left on Fairground Road.