From a Rail Trail to a Fire Tower: Hiking Trails in Wilmington
July 11, 2026
From easy walks to more challenging climbs, Wilmington has a trail for every hiker.
Over the years, Wilmington has impressively stitched together a web of trails that connect downtown to mountain views, rivers, streams, and deep woods.
Rail trails, mountain climbs, and forest paths can be found throughout town, thanks to decades of volunteer work. Maintaining and improving these trails is about making sure everyone in the community has access to the outdoors.
“We tried to remove as many barriers as possible so that anyone who wants to experience the outdoors here can do so, regardless of their age or physical ability,” says Joanne Yankura of the Wilmington Trails Committee.
-Main Street in Wilmington on Route 9.
Hiking is consistently ranked as popular activity for visitors to Vermont.
“Every summer our Visitor Center welcomes countless people looking for trail recommendations,” says Tim Dolan, director of marketing for the Southern Vermont Deerfield Valley Chamber of Commerce. The chamber recently compiled a new hiking guide to showcase the many trails around town.
“Whether someone is looking for a family-friendly walk, a scenic summit, or a more challenging adventure, this guide helps visitors spend less time planning and more time enjoying everything the Deerfield Valley has to offer,” Dolan says.
Four Wilmington Hiking Trails to Explore
If you’re looking for a good hike, Wilmington has plenty of options. Take a gentle stroll on the Hoot, Toot & Whistle Trail, climb to the Mount Olga Fire Tower, wander around Lake Raponda, or take a longer trek on the Primitive Trail.
-The Hoot, Toot & Whistle Trail follows the old Hoosac Tunnel & Wilmington Railroad bed.
Hoot, Toot & Whistle Trail
The Hoot, Toot & Whistle Trail is a two-mile path follows the old Hoosac Tunnel & Wilmington Railroad bed toward Harriman Reservoir/Lake Whitingham and ends at the Mountain Mills East picnic area and boat launch.
The rail bed was engineered for narrow-gauge trains, giving hikers a wide, level path through the woods and near the water. You can access the trail from a foot bridge off West Main Street in Wilmington. Other access points include the end of Mill Street and midway on Fairview Avenue.
-The view from the Mount Olga Fire Tower at Molly Stark State Park. Photo by Tim Dolan.
Mount Olga Fire Tower
If you want a classic Wilmington hike, head for the Mount Olga Fire Tower. You can take the quickest route from the Hogback Mountain overlook on Route 9 in Marlboro by setting out on the the Tower Trail. For a more challenging hike, opt for the 1.7-mile Mount Olga Trail Loop at Molly Stark State Park.
Either way, you’ll end up at the fire tower, where the views stretch across Vermont, Massachusetts, and New Hampshire. The fire tower, which was moved to Molly Stark State Park from Bald Mountain in Townshend in 1955, rises about 50 feet above the summit of Mount Olga.
Historical remnants of the former Hogback Ski Area, a lost ski area that operated between 1946 and 1986, can be found on the east side of Mount Olga.
-Trails around Lake Raponda in Wilmington offer both shorter loops and longer treks.
Lake Raponda and Raponda Ridge Trails
The Lake Raponda trails on the eastern side of the lake are accessible on Lake Raponda Road. Start near Green Mountain Beach and take the Town Forest Loop. There’s also a self-guided tree walk.
You can opt for longer routes on the Raponda Ridge Trails from Ware Road that connect to the Hogback Mountain Conservation Area. Hogback is a nearly 600-acre preserve in Marlboro where you can hike through forests and former ski trails, see wildlife, and enjoy stunning views.
-Find old forest growth, beaver ponds, and ridge crossings on the Primitive Trail.
Primitive Trail
Locals recommend the Primitive Trail, a 5.8-mile out-and-back trail connecting White’s Road to Lake Raponda. This moderate hike features an elevation gain of 889 feet, old forest growth, beaver ponds, and ridge crossings. Since it’s not a loop, most people park a car at each end and walk it one way.
The trail covers several cross-country and snowshoe trails previously maintained by The White House Inn on Route 9, east of downtown. Volunteers from the Wilmington Trails Committee have been looking after the trail since the early 2000s.
-A trail head at Lake Raponda.
Making the Connection
The abundance of trails in and around downtown Wilmington came together by locals figuring out what already existed.
“The existing variety of trails came together rather serendipitously,” Yankura says. “The network was largely born out of making use of what was already available in various forms and tying things together.”
In the late 1990s and early 2000s, the trails committee believed that downtown should be more than just a place to park. So, they set out to turn Wilmington into a hub for trails with a variety of terrain.
Volunteers started linking up old rail beds, logging roads, snowmobile tracks, ski trails, and forgotten town roads.
A view of Vermont’s Deerfield Valley in Marlboro.
Enhancing the Local Outdoor Economy
Depending on where you hike in Wilmington, you’ll cross public, conserved, and private land.
“In Vermont, around 70 percent of public trails, cross private land,” Yankura says. “So we’re grateful to the private landowners who give permission for these trails to exist and continue to exist.”
The Hoot, Toot & Whistle Trail runs through conservation land owned by Great River Hydro, while other trails wind through town forests, state parks, national forest, or private property.
The committee is also working on accessibility, better links to the future Velomont Trail, easier walks between trails and downtown, and teaming up with neighbors across the valley.
“This initiative has also aimed to create a more pedestrian-friendly downtown,” Yankura says.
She says the committee also wants to make the entire trail system easier to use, keep walkers safe between the trails and downtown, and develop a plan to keep bridges and boardwalks in good shape for the long haul.
“We’re trying to continue making connections between the trail network and the local outdoor economy,” Yankura says. “And the goal is to make the trails sustainable and accessible for years to come.”
Find more trails in the Southern Vermont Deerfield Valley Chamber’s new hiking guide.