If you’re looking for an easy walk that ends at Vermont’s largest lake, the Hoot, Toot & Whistle Trail in Wilmington delivers exactly that. This flat, roughly 2-mile rail trail follows an old railroad bed through the forest, parallels the North Branch of the Deerfield River, and drops you at the shore of Harriman Reservoir. The whole thing takes about an hour out and back, and it’s one of the most family-friendly trails in the area.
We send guests at Valley View Villa here all the time – especially families with younger kids who want a real trail experience without the elevation.
The Railroad That Gave It Its Name
The trail follows the abandoned bed of the Hoosac Tunnel and Wilmington Railroad, a narrow-gauge line built in the 1880s to serve the Deerfield Valley. Locals looked at the initials – HT&W – and started calling it the “Hoot, Toot & Whistle.” The railroad hauled materials for the construction of both Somerset Dam and Harriman Dam before a 1936 flood destroyed a bridge and shut down service to Wilmington for good.
Today, interpretive panels along the trail mark the spots where industrial buildings once stood. It’s a nice layer of history on what would already be a pleasant walk.
What the Trail Is Like
🥾 About 2 miles one way (4 miles out and back)
🌳 Flat packed-earth and gravel surface – follows the old railroad grade, so minimal elevation change
🐕 Dogs welcome on leash
🚲 Bikes allowed, though some sections are better suited for walking
The trail starts at Reardon’s Crossing footbridge, just off West Main Street in downtown Wilmington. From there you head north through mixed hardwood forest, with the river occasionally visible through the trees. The path is shaded most of the way – a real benefit on hot summer days.
The trail recently underwent a major renovation that widened the path, added new bridges and boardwalks, and improved drainage. There’s also a new parking area at the Harriman Reservoir end on Fairview Road.
The Payoff at the End
The trail terminates at Harriman Reservoir – a 2,000-acre lake surrounded entirely by forest. At the Fairview Avenue end, you’ll find a boat launch, a picnic area, and access to the water. In summer, it’s a perfect spot to cool off after the walk. Bring a lunch, spread out on the grass, and enjoy the view before heading back.
If you want a longer lake day, Wards Cove on the east shore has a beach and swimming area.
Getting There
From West Dover, take Route 100 south to Wilmington (~12 minutes). Park in the public lots on West Main Street or South Main Street, near the Reardon’s Crossing footbridge. You can also access the reservoir end via Fairview Road if you’d rather start at the lake and walk back toward town.
Good to Know
🕐 Plan about 1–1.5 hours for the full out-and-back at a casual pace
🗺️ The trail connects to the Riverwalk (0.4 miles along the Deerfield River in downtown Wilmington) and the Beaver Brook Trail – so you can extend the walk if you want more
☀️ Best from May through October. Fall foliage in late September makes this one of the prettiest walks in the valley.
🚌 The free Moover shuttle runs between Dover and Wilmington in ski season – handy if you want a one-way hike with a ride back
This is the kind of trail that works for everyone – morning dog walk, afternoon family stroll, or a quick escape into the woods before dinner. And ending at the largest lake in Vermont doesn’t hurt.
Find more outdoor adventures at Valley View Villa’s blog.
More to Explore
- Cycling the Valley Trail: Dover to Wilmington
- Swimming at Wards Cove on Harriman Reservoir
- Fishing at Harriman Reservoir
- Waterfall Hikes Near Mount Snow – 7 Cascades Worth the Trek
Frequently Asked Questions
How long is the Hoot, Toot & Whistle Trail?
The trail runs about 2.5 miles one way from downtown Wilmington to Harriman Reservoir. Plan roughly 1-1.5 hours for the full out-and-back at a casual walking pace.
Is the Hoot, Toot & Whistle Trail kid-friendly?
Very much so. The trail is flat, wide, and well-maintained — perfect for strollers, young kids, and dogs on leash. Families staying at Valley View Villa often use it for a morning outing.
Can I bike the Hoot, Toot & Whistle Trail?
Yes. The flat, packed surface works well for bikes. It connects to the Valley Trail system and the Riverwalk in downtown Wilmington, so you can extend your ride if you want more distance.
Where do I park for the Hoot, Toot & Whistle Trail?
Park in the public lots on West Main Street or South Main Street in Wilmington, near the Reardon’s Crossing footbridge. You can also access the trail from the reservoir end via Fairview Road.
