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 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

4. Riverwalk

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, descends steeply to cross a tributary via wooden footbridge, and then veers acutely left to ascend a very steep and more challenging section of stepped terrain, leading to the ridge above.

From there it is more gentle, crossing through old forest, old cross country ski trails, high ridges and low beaver ponds, eventually arriving at a trail head on West Lake Road on the west side of Lake Raponda. This trail offers a beautiful hike through evergreen and mixed hardwood forest. Park one car at the West Lake trail head, hike the trail to White’s Road, and enjoy lunch and a ice cream cone at Wahoo’s! 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.

8. 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.

9. 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. 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. The third option is a family friendly loop back to Buzzy Towne Park.