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Hiking in the Green Mountains

Hiking in the Green Mountains of Vermont

Hiking Trails To Discover

Deer Leap at Sherburne Pass, Killington (moderate) – From Killington Chamber, take a left onto Rt. 4 West up to Pico Pass. Park at the Inn at Long Trail.  Trailhead is on the right side of the building.  Deer Leap is a rock outcrop with panoramic views of Coolidge Range, Sherburne Pass and Pico Mountain. When completing your adventure, reward yourself with a cold drink at The Inn at Long Trail. The inn, which was built in 1938 around the outcroppings of Sherburne Pass, provides interesting décor and hospitality second to none. 3.1 miles. Elevation Change: 600 feet, 1 ½ - 2 hrs. 

Sherburne Pass Trail to Pico Peak, Killington (difficult) - From Killington Chamber, take a left onto Rt. 4 West up to Pico Pass. Park on left across from the Inn at Long Trail.  This challenging and often steep trail climbs nearly 1,900 vertical feet. 

Gifford Woods State Park, Killington (easy, family friendly) – From Killington Chamber, take a right onto Rt. 4 East, and take a left onto Rt. 100 North.  Parking lot will be on your left.  Follow the Kent Brook Trail for an easy one-mile hike in the woods. The trail passes through a beautiful mixed age northern hardwood forest. The trail is marked with yellow blazes and begins at the “STOP” sign near the contact station, circles the campground, crosses the Appalachian Trail and ends in the lower campground loop between Cherry and Aspen lean-tos. 1.1 miles.  Public restroom and maps.  At Gifford Woods, you can also hike south on the Appalachian Trail up to Deer Leap.

Kent Pond, Killington (easy-moderate, family friendly) - From Killington Chamber, take a right onto Rt. 4 East, and take a left onto Rt. 100 North.  Parking area will be on your right. The trailhead is on the right side of the parking lot near the road.  Follow the white trail blazes through Kent Pond Access, over Kent Brook’s cascading pools, past the grassy opening at Mountain Meadows Lodge. From here you can turn left onto Thundering Brook road and walk along the road over the dam, and then turn back the way you came (45 min round trip).  Alternatively, for a longer hike you can follow the white blazes across the road, which will bring you to Thundering Brook Waterfall.  Veer off the main trail and follow yellow blazes to see the brook, and a series of stunning pools and waterfalls. (About 2 hours round trip)

Buklin Trail, Mendon/Killington (difficult) – From Killington Chamber, take a left onto Rt. 4 West and follow for about 5.3 miles.  Take a left onto Wheelerville Road and follow for 2 miles to the Buklin Trailhead.  A nice, secluded and difficult hike up to Cooper’s Cabin and the peak of Killington.  7.8 miles round trip.

Bald Mountain, Mendon (moderate-difficult) – From Killington Chamber, Take a left onto Rt. 4 West and follow to the blinking light (at Best Western) and take a left onto Town Line Road.  Follow Town Line Road to Notch Road to Tamarack Notch Camp, Part of Aitken State Forrest.  High peaks and great look outs.   4.1 mile, 3 hours round-trip.

Blue Ridge Mountain via the Canty Trail, Mendon (moderate) – From Killington Chamber, take a left onto Rt. 4 West.  Take a right onto Old Turnpike Road, just past the Cortina Inn.  Small parking area is on your left at about .6 miles (you will see a gate, do not block the lane). Walk around the gate and down the lane.  The trail (blue blazes) bears right from the lane just before passing buildings of a former camping area.  The trail crosses several brooks and climbs more steeply alongside a larger brook.  Leaving the brook, the trail becomes less steep and arrives at the summit.  3.5 hours and 5 mile roundtrip. 1,700 feet elevation gain.

New Boston Trail, Chittenden (moderate) – (11 miles from Killington) From Killington Chamber, take a left onto Rt. 4 west and follow to Mendon for 7 miles.  Take a right onto Meadowlake Drive (following signs for the Mountain Top Inn).  Take a right turn onto Chittenden Road (2.7 miles) and then take a slight left onto Mountain Top Road.  Circular trail starts at the end of Mountain Top Road and climbs to overlook Chittenden and completes a tour around the reservoir.  Stop by the Mountain Top Inn for information or a refreshing beverage on their outdoor patio!

The Faulkner Trail, Woodstock - The walk is about 30 minutes for the average hiker and provides a magical view of Woodstock. Note that reaching the summit requires sure-footed-ness at the top as the trail gets steep, narrow and rocky for the last hundred yards or so. From the Town Green, walk over the Covered Middle Bridge in the Center of Woodstock to River Street, go straight on to Mountain Avenue that will bear left, as a dirt road. Enjoy the stately architecture of the homes as you head to Faulkner Park, just beyond the lovely white Faulkner Mansion (a private home .

River Street Cemetery Trail, Woodstock- A less traveled trail with fewer markings. From the Green walk over the Covered Middle Bridge in the center of Woodstock to River Street, go right onto River Street and walk until you see the River Street Cemetery on your left. Walk to the very end of the stone wall and turn left onto the trail through a stand of elegant pines. This trail will take you past the Swift Water Girl Scout overnight cabin and up to the Link Trail. Or bear right to walk to the trails at the Marsh Billings Rockefeller Historic National Park. 

Prosper Road Trail Head, Woodstock- Ample parking for longer hikes with an easy grade and wide carriage roads. Drive from the center of Woodstock heading north on Route 12 about 1.5 miles to the small green sign "To West Woodstock". Turn Left on Proper Road and head up this dirt road about 1.3 miles to an obvious parking area in a stand of pine trees on your left. You can leave your car there during the day, just not overnight. The trailhead is well marked and maps are often available.

Killington Resort Gondola & Hiking

Enjoy K-1 Gondola-serviced hiking on 15 miles of signed hiking trails. Explore the beauty and nature of Killington’s six peaks up close, including the 4,241-foot summit of Killington Peak. The K-1 Gondola is open (weather permitting) from 10 a.m. to 5 p.m from late June - mid October.

For more information, see the Gondola Rides page.

Download a Visitor Guide

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