Raponda Ridge loop:
June is a good time to walk the Raponda Ridge Trail because the lupins are in bloom. From the trail head on Ware Road, walk past the gate and follow the blue diamonds for .3 miles, then turn right onto the Raponda Ridge lower trail. Bear right and follow the babbling brook down and then up for .4 miles to a tee. A right turn here would take you to the Hogback Mountain trails, but instead turn left to follow the Raponda Ridge upper trail back. Follow the blue diamonds through the woods for .7 miles then back to the trailhead.
Old Stage Road loop:
From the Lake Raponda Trail head above the Green Mountain Beach parking lot, walk uphill a few yards to a marked intersection and turn right toward Stearns Avenue. You can find another geocache as you walk through woods. At Stearns Avenue, walk uphill for a short distance, then veer off Stearns Avenue to the right. A stone tower once stood in the field to your left, but birch trees now grow out of those stones. This trail connects with Ware Road (turn left), and continues as a trail. You’ll pass the trailhead of the Ware Road-Hogback Connector Trail and continue on to Old Stage Road–so called because it was once the main road to points east. Continue downhill on Old Stage Road to the intersection with Lake Raponda Road. Turn left, stroll past the boat launch and return to your starting point at Green Mountain Beach.
Ware Road loop:
From the Lake Raponda Trail head above the Green Mountain Beach parking lot, walk uphill a few yards to a marked intersection and turn right toward Stearns Avenue. You can find a geocache as you walk through woods. At Stearns Avenue, walk uphill for a short distance, then veer off Stearns Avenue to the right. A stone tower once stood in the field to your left, but birch trees now grow out of those stones. This trail connects with Ware Road (turn right). You’ll pass the Raponda Ridge trail head and continue downhill to the intersection with Lake Raponda Road. Turn right to return to your starting point. As you pass Stearns Avenue, stop by the Little Free Library and pick up a book. It’s about 2.5 miles in all.
Town Forest loop:
From the Lake Raponda Trail head above the Green Mountain Beach parking lot, walk uphill a few yards to a marked intersection and turn left or go straight for a .3 mile loop through the woods of the Wilmington Town Forest. You can find a geocache and a spring house along the way.
From the Raponda Ridge trail head, hike north on Ware Road. The road becomes a trail, and shortly thereafter turn right onto the Ware Homestead & Hogback Connector Trail. Follow it for about a mile, entering the Hogback Mountain Conservation Area. Turn right at the tee, then after the bridge turn left onto the snowmobile trail. Follow it for about a mile to Old Hogback Road and turn left. At the cell tower turn right and you’ll pop out at the Hogback overlook for a fantastic view. Here you’ll also find the Beer Naked Brewery, Metcalfe Vermont Distillers, the Southern Vermont Natural History Museum, and the Hogback Mountain Gift Shop. To return, go back to Old Hogback Road and turn left at the cell tower. Follow it to Route 9 and walk a few yards onto Sun & Ski Road. Turn right onto the snowmobile trail and continue to the Raponda Ridge trail. Follow it and bear left after the bridge to return to the Raponda Ridge trail head. It’s about 4 miles in all.
Sun and Ski loop:
From the Raponda Ridge trail head, hike south on Ware Road. Continue straight onto Not-A-Rd and straight onto the trail. Turn left at the dirt road, left onto Sun & Ski Rd, right onto Theresa Ln, and continue for a half mile. Turn left onto the trail at pole 15987 with a blue diamond. Follow the blue diamonds to the Raponda Ridge trail sign and turn left. Follow the blue diamonds across the bridge and through the woods to the next trail sign, then take the Raponda Ridge upper trail back to the trail head. It’s about 3 miles in all.
Hoot, Toot & Whistle loop:
So named because it roughly follows the Hoosac Tunnel and Wilmington (also known as Hoot, Toot and Whistle) railway bed. Start at Reardon’s Crossing footbridge. Follow this trail to the right (west and south) of the Village. It follows the North Branch of the Deerfield River and then south along the shore of Lake Whitingham until it reaches the boat launch and swimming area. Distance: 2.0 miles. To create a 4.0 mile loop, return via Fairview Avenue. Turn left onto Castle Hill Road and then left onto West Main Street to return to Wilmington center.
Historic Downtown Wilmington loop:
Cross Reardon’s Bridge and begin at the kiosk. Follow the gravel path with interpretive displays. At the fork, stay left for a steeper route or stay right for a more moderate route uphill. At the trail junctions, turn left and follow the Hoot Toot and Whistle trail to the end. Exit and turn right onto Mill Street. Just beyond the MOOver driveway, turn left and follow the grassy path. Turn right onto the gravel path and return to Reardon’s Bridge.
Interpretive signs describe business ventures here dating back to 1914 that contributed significantly to Wilmington’s economy. The loop walk covers land once traversed with train tracks and rail yards for a logging railroad, the Deerfield River Railroad, and a logging/passenger/freight train, the Hoosic Tunnel & Wilmington Railroad Company. The DRR provided a direct connection and rich supply of timber from surrounding logging operations to local factory businesses. The HT&W opened Wilmington to the world by transporting area residents, locally produced goods, logs, and tourists.