1. The Valley Trail
Park in any public parking lot in the center of Wilmington. At Reardon’s Bridge, use the crosswalk to the north side of Route 9, then walk a few yards west to the trail head. Proceed up a short steep incline to the top of the ridge heading west behind businesses and inns on your left and orchards and fields on your right. You will see the wind turbines in Searsburg and a brook on your right before crossing two wooden bridges. When you see a large Vintage Motel sign on your right, cross the field directly ahead and enter the woods on the far side. Follow the trail and cross Chimney Hill Road. Follow the blue diamonds past the Chimney Hill tennis courts and parking area on your left. Continue across the field and enter the woods. Continue on the Chimney Hill trails, crossing several roads until you reach Forbush Road. Turn left and follow the road until you see a trail on your left and a house on the right. Take this trail to a clearing with power lines and fields. From here you can continue north to West Dover. The map of the whole Valley Trail is here.
2. Hoot, Toot & Whistle Trail
So named because it roughly follows the old Hoosac Tunnel and Wilmington (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. A brief history of the railroad is here. 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 West Main Street 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
4. Beaver Brook Trail
The Beaver Brook Trail is fairly short (.7 mile) and level, great for those who want a more leisurely walk and don’t necessarily need to be deep in the woods. It follows Beaver Brook from Buzzy Towne Park on South Main street, a good place to park and for kids to play. It then goes past the town tennis courts, through the “Old School Community Center” ball field and continues on to a point where it intersects with Rte. 9, east of town. At that juncture, hikers can opt to turn left and go into town or right to follow Rte 9 to The Primitive Trail. Going left or right will bring hikers past stores and places to get a bite to eat.
5. Lisle Hill to White’s Road
From Wilmington Center, head North on Route 100 and turn almost immediately onto Lisle Hill Road. The trailhead is located on the left, about 0.5 miles after passing Old Town Common, the site of Wilmington’s original town center built back in 1780. Roadside parking at the trailhead is permissible year round. Use caution when parking in the nearby field; it is quite rugged and often muddy in wet seasons. Open, mixed forest scenery surrounds the serene trail throughout with some steep areas and rugged terrain. Soon after the initial descent, the trail turns right, merging with a wider snow mobile trail. Further on, the trail splits to form “the lollipop” offering two directional choices: straight, the hiking-only trail continues and ends at upper White’s Road; turning right, the trail follows the snow mobile trail and ends at lower White’s Road. Both trails may be combined into a 1.1 mile “lollipop loop” back to Lisle Hill trailhead.
6. Primitive Trail (White’s Road to West Lake Road)
This trail begins on the east side of White’s Road, just north of Route 9. It follows Beaver Brook, then rises steeply onto a ridge. From there it is more gentle, traversing old forest, ski trails, ridges, and beaver ponds, eventually arriving at the trailhead on the west side of Lake Raponda. Distance: 2.75 miles
7. Lake Raponda Trails
These trails are on the east side of Lake Raponda. The trail head is on the east side of the parking area above Green Mountain Beach on Lake Raponda Road. From the trail head, walk uphill a few yards to a marked intersection. If you turn left, you can stroll the short Wilmington Town Forest Loop. If you turn right toward Stearns Avenue, you can enjoy the longer Ware Road loop or Old Stage Road loop.
9. Raponda Ridge Trails
Follow Ware Road for 0.7 miles and park at the Raponda Ridge trail head on your right. The trails are well marked and have a comfortable walking loop with a babbling brook. These trails also connect to the Hogback Mountain Conservation Area‘s trails which continue to Hogback Mountain and Mount Olga.
8. Ware Homestead & Hogback Connector
This beautiful and bucolic trail can be accessed via the Green Mountain Beach Parking lot or from the Raponda Ridge Parking area. It often follows ancient roads, and passes through what was once known as “East Wilmington,” a high elevation little hamlet nestled below Hogback Mountain and occupied predominantly by the Ware family. In this area you will pass by old cellar holes, 200-year-old maple trees, farmland, and seemingly endless stone walls which were once the Ware farm. This trail also features thick coniferous spruce forest landscape as you head from Raponda Ridge toward the Hogback Mountain Conservation area. This trail can also be used to connect to the Hogback Mountain Conservation area where plentiful trail choices and connections exist. One can continue through to Molly Stark State Park in a southerly direction, which connects to the Shearer Hill Trail for those seeking a longer hike.
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 trail head 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.
11. Monument Trail
A mostly gravel footpath from the parking area behind St. Mary’s in the Mountains Episcopal Church down to the Beaver Brook Trail.