Vermont Hiking Trails Near Woodstock & Killington

“Thousands of tired, nerve-shaken, over-civilized people are beginning to find out going to the mountains is going home; that wilderness is a necessity….” –John Muir

Vermont is unique in the Northeast for easy access to an expanse of wilderness. The Green Mountains are laced with hiking trails. Some of these local hiking options are listed below. Hikes are either loops, where you start and end at the same point; out-and-back, where you walk to a point and then backtrack; or point-to-point, where you leave your vehicle at the end point and get shuttled to the beginning point. Chuck and Edie are avid hikers familiar with the local trails, and happy to talk to you further as well as provide maps, and directions.


There is limited Appalacian Trail parking at a small dirt lot located on Route 12 about 4 miles north of Woodstock. From this trailhead, either out-and-back or point-to-point hiking is available. Point-to-point hike options include a 5.5 mile hike from the Lookout Farm Road trailhead, or a 6.6 mile hike from the Cloudland Road trailhead. Both options offer scenic views.


A large Appalacian trailhead parking lot is located on Route 4 just west of the Pico Mountain Ski Resort. A popular 6 mile Appalacian Trail point-to-point hike from this trailhead passes through Gifford Woods State Park, skirts Kent Pond, passes by Thundering Brook waterfall and ends at the River Road trailhead. This hikes distance can be shortened by 2 or 3 miles by starting at different points.


This 7 mile loop hike can be started from either the Appalacian trailhead mentioned above, or the Sherburn Pass trailhead located about one-half mile east on Route 4. In either case, the trail climbs about 1,600 ft with a short spur-trail option to the top of Pico Mountain. This hike can be combined with the above described 6 mile Appalacian Trail hike for a 13 mile point-to-point hike.


The trailhead is located on Wheelerville Road, off Route 4 in the town of Mendon. The Bucklin Trail is a 7 mile round trip, 2,500 foot climb, out-and-back trail crosses the Appalacian Trail on it way to the granite outcrop summit of Killington Peak where you will be rewarded with a three-state view. Because the trailhead is more out of the way, this hike is generally less crowded than the hikes from the Route 4 trailhead.


This 4 mile round trip, 1,500 foot climb, out-and-back hike begins at a little used gravel trailhead on the CCC Road about 3.5 miles west of Route 100 in the town of Plymouth. The trail is not well maintained but well marked. This hike can be extended to where it intersects with the Appalacian/Long Trail northbound for a bit and then off a short spur-trail leading to the summit of Killington Peak at 5.6 miles one way, and 2,600 feet of climbing.


There are three general access points to this several hundred acre National Park forest located outside of Woodstock. Ample parking at the Billings Farm and Museum allows access to the miles of hiking trails and carriage roads that criss-cross the Park grounds. A popular 3 mile round trip loop hike from Woodstock to Mount Tom is accessible from the town of Woodstock. A slightly more remote trailhead on Prosper Road allows access to the far side of the Park’s carriage roads and hiking trails.

To view availability enter your arrival date and stay duration below: