Woodstock Vermont Hiking Trails

Woodstock Vermont hiking trails offer easy access to an expanse of wilderness. Hiking trails lace the Green Mountains. Below is a sampling of these local hiking options. A loop hike starts and ends at the same point. In an out-and-back hike, you walk for some distance and retrace your steps to where you started. In a point-to-point hike, leave your vehicle at the end point, and shuttle to the beginning point.  Chuck and Edie are avid hikers familiar with the local trails.  We will happy to talk to you further. We also provide maps, and directions.

“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

Edie hugs a tree at Thundering Brook falls.APPALACIAN TRAIL NEAR WOODSTOCK:

Limited Appalacian Trail parking is available at a small lot beside 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. Starting at different points shorten this hike’s distance by 2 or 3 miles.

Viewpoint on the Slack Hill trail in Calvin Coolidge State Park.SHERBURNE PASS TRAIL:

This 7 mile loop hike is 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. It’s extended to a 13 mile point-to-point hike when combined with the above described 6 mile Appalacian Trail 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 crossing the Appalacian Trail.  It terminates at the granite outcrop summit of Killington Peak.   From here, on a clear day, you are rewarded with a three-state view.

A section of the Appalachian Trail.SHREWSBURY PEAK TRAIL:

This is a 4 mile round trip.  The trail is a 1,500 foot climb, out-and-back hike. It 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 is extended by following the trail to where it intersects with the Appalacian/Long Trail.  At this point, go northbound for a bit, and then take a short spur-trail leading to the summit of Killington Peak.  This route is  5.6 miles one way, and involves 2,600 feet of climbing.


There are three general access points to this several hundred acre National Park forest located outside of Woodstock. There is ample parking at the Billings Farm and Museum.  From here,  multiple points allow 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.

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