1. The Valley Trail
Park in any Public Parking lot in the center of Wilmington Village. Start at Reardon’s Crossing footbridge. Cross to the North side of the street and travel briefly along the road (west). The trailhead will be on your right. This trail travels all the way to Dover. Distance: 9.0 mile. See the complete bi-town valley trail map for parking options and multiple trail heads for access.
2. Hoot, Toot & Whistle Trail
So named because it roughly follows the old Hoot, Toot & Whistle railway bed. Start at Reardon’s Crossing- the footbridge. Follow this trail to the right (west and south) of the Village. It follows the North Branch of the Deerfield River and then heads south along the shore of Lake Whitingham until it reaches the Boat Launch and Swimming area. Distance: 2.0 miles (4.0 mi. r/t)
3. Downtown Loop
Start at Reardon’s Crossing foot bridge on the west side of the village. Cross over the bridge and stay left, turning onto Mill Street, to Shafter Street. Turn left again onto South Main Street. Finally, turn left to walk along the river and behind Crafts Inn, back to your starting point at Reardon’s Crossing. Or weave your way in and out of the quaint shops and delicious restaurants in the village as you complete this short tour of the village. Distance: 0.5 miles
Part of the HT&W trail to just past the Moover building. Starts opposite Dot’s restaurant, goes behind Craft’s Inn, using the West Main Street parking lot, to Reardon’s Crossing foot bridge. Cross bridge, follow trail to the right, between the Mover building and the river, turn left up the hill to connect to the HT&W trail. Distance: 0.5 miles
5. Lisle Hill to White’s Road
From Wilmington Center, head North on Route 100; turn almost immediately right onto Lisle Hill. Park 0.5 miles up the hill near the old town common. Trailhead is just uphill from there on the left. The trail goes over Lisle Hill with some rugged steep sections. There are two connections onto White’s Road, which allow for a 1.1 mile total “lollypop loop”. Returning to Lisle Hill via Route 9 results in a 2.4 mile loop. Or continue across White’s Road and connect onto the Primitive Trail.
6. Primitive Trail (White’s Road to West Lake Road)
This trail begins on the east side of White’s Road, just after crossing the bridge over Beaver Brook. The Trail briefly follows Beaver Brook, descending steeply to cross a tributary, then rising steeply onto the ridge. From there, it is more gentle, crossing through old forest, old cross country ski trails, high ridges and low beaver ponds, eventually arriving at the southwestern shores of Lake Raponda. Distance: 2.75 miles
7. Lake Raponda Trails
These are on the east side of Lake Raponda. Access the trailhead by parking in the designated lot for the Green Mountain Beach, on Lake Raponda Road.
From here, you can access a short (0.3mile) loop, through the woods of Wilmington Town Forest. Start from the northeast corner of the parking area, and head left.
Alternatively, head right from the northeast corner of the parking lot, and you will pick up a longer loop. This trail passes through woods, then connects with Stearns Avenue (uphill) for a short distance. It then veers off Stearns Avenue to the right, eventually connecting with Ware Road (take a left), and continues as a trail to Old Stage Road. At the end of Old Stage, turn left and walk along Lake Raponda Road to return to the parking area.
8. Raponda Ridge Trails
Follow Ware Road for 0.7 miles to Raponda Ridge gate and trail head on your right. Follow the blue trail markers. This trail loops back to the trailhead for a 1.3 mile hike. This trail also connects to the Hogback Mountain Conservation Area Trails (see “Other Publicly Accessible Trails”)
9. Ware Homestead & Hogback Connector
You can park at the Green Mountain Beach Parking lot or the Raponda Ridge Parking Area. This is a 1.1 mile trail (one way) from its junction with Lake Raponda Trail. It connects to the Hogback Mountain Conservation Area trails, through to Molly Stark Park in a southerly direction, connecting to the Shearer Hill Trail.
10. Shearer Hill Trail (to Mt. Olga)
Park at the Intersection of Shearer Hill and Parsons Road, on the right, just past the quarry. The trailhead is reached by walking along Shearer Hill Road for approximately 0.5 miles. You will find it on the left hand side of the road. From the parking spot, this trail is 1.5 miles one way, and includes a very steep section at the beginning. After 1.5 miles, it connects with Molly Stark State Park’s trails and the Hogback Mountain Conservation Area trails (see “Other Publicly Accessed Trails”)