Hiking & Walking

In addition to all the walks & hikes below, find trail maps for the entire state here.

A Walk with History:

For a pleasant walk and a glimpse of Okemo Valley history, the Branch Brook Trail is a good choice. The trail head is located off Rt 131. From the junction of RT 106 proceed East on Route 131 taking the first Right onto Branch Brook Road. The small parking area is located one mile down the Branch Brook Road. The trail was opened in 2004 and is marked by White blazes as it follows parts of the old Branch Brook Road, Crown Point Military Road. (this portion marked with yellow paint.) One of the original Crown Point Road markers is on the trail. You will reach the shoreline of Stoughton Pond and follow the trail to the Recreation area. Stoughton Pond covers 65 acres and is part of a flood control area. Total round trip 2.5 miles, Time 1.5 hours but take time to linger and enjoy the views as there are several overlooks at Stoughton Pond and BranchBrook. Enjoy the walk.

Inn to Inn Walking Tour:

As seen in May issue of Yankee Magazine

Vermont Inn to Inn Walking Tours offers the most independent and relaxing way to observe Vermont’s natural beauty while staying in Vermont bed and breakfasts. Each day’s tour is unique and offers varying terrain ranging from “nearly flat” to “gentle slopes” and “steady uphill/downhill grades.” Set your own pace and walk as much or as little as you wish.The routes are determined to provide you with the most fruitful experience. However if you choose to do smaller segments, we can make arrangements to pick you up along the way and transport you to the next inn along this Vermont tour. Here is how it works: You will arrive at one of the Southern Vermont inns the evening before the walk. The next morning after breakfast, you will be given a route map and snacks for the day. Your route will average approximately 10 miles. The Innkeeper will transport your bags to the next bed and breakfast, so that your bags are ready for you when you arrive later in the day. At the next B&B, you will have the opportunity to clean up, relax and enjoy a great evening meal (specialty dish) prepared by the Innkeepers. The next three days each offer another great country/gourmet breakfast, a different route leading to the next B&B, another great evening meal, and an experience of a lifetime! For more information visit To make reservations in the Okemo Valley, contact The Combes Family Inn at 802-228-8799 or Inn Victoria at 802-875-4288.

Take a hike!

Chester boasts much in the way of artisans, antiques and a famous “Chester Craft Fair” but did you know there’s a few prized walks and hikes you can explore too?  Check out the Lost Mine or GMUHS hikes to see the natural wonders of our area.

There are many day hikes around the Okemo Valley. For more details and trail conditions contact the Chamber Office, or purchase a copy of “50 Hikes in Vermont” which is available in local book stores.

To easily download the  walks/hikes listed below simply click this link:  Hiking Okemo Valley

Remember: Please carry out all trash. Leave nothing but your foot prints. Take nothing but memories.

Easy Walks

Lowell Lake Trail 3.5 miles R/T

Lowell Lake is located off Route 11 on Lowell Lake Road which is adjacent to the Magic Mountain access road. Proceed on Lowell Lake Rd until you reach a House on the left and a Barn directly across on the right. Turn right and follow to the parking lot. The 3.5 mile trial begins on the Dam and circumnavigates this small lake with its large selection of wildlife and great views across the water. Time: Two and a half hours Spring & Summer. Add one hour Winter. Good snowshoe and cross country ski terrain.

Slack Hill Trail: (2.5 miles) Blue blazes. Coolidge State Park.

The Slack Hill Trail begins at the park office, climbing moderately for the first ½ mile through hardwoods; then a short steep section continues to a trail intersection. The trail on the right descends back to the park road just above the office. The main trail continues left climbing moderately for one mile before descending a short distance to a vista located near the 2,174 ft summit of Slack Hill. On clear days Mount Ascutney can be seen in the distance. The trail continues alternately climbing and descending for another mile to the day use area parking lot. Day fee charged during operating season. Finding the Trailhead: Head north on VT-103 and turn right onto VT-100N in 1.5 miles.  Continue on VT-100N 8.7 miles.  Turn right onto VT-100A and drive 2.7 miles.  Turn right onto Coolidge State Park Rd.  The trailhead is on the left (behind the Ranger station.)

Vista Trail 1.5 miles R/T

Located at Camp Plymouth State Park Distance .75 miles, Elevation Change 200 feet. Trail head is located at the State Park and leads to an overlook of the lakes area. Located off Route 100 North, turn onto Plymouth Tyson Road at the Echo Lake Inn, follow 1 mile to Boy Scout Camp Road turn left to Camp Plymouth State Park. Time one hour Spring & Summer. Add .5 hour Winter. An unmarked old logging road provides access to the Buffalo Brook basin for a distance of more than 5 miles. Good Snowshoe terrain. Upper portion is used by Snowmobiles. Entry Fee charged Memorial Day to Labor Day.

Ludlow Walk 2.5 miles

From Veterans Memorial Park across Rt 103 from the Library.
Proceed South along Route 103, passing Black River High School continue to the Timber Inn,
Turn Right crossing the Black River onto Pleasant St Extension, follow as the street turns Right and become Pleasant St.
Continue to follow to the Route 100 – Andover St intersection.
Turn Right return to Route 103 and Turn Left. Follow passing the Fire Station, turn Right crossing the Black River onto Dug Road.
Follow up the hill (one way oncoming traffic) stay straight passing Black River Academy Museum.
Veterans Memorial Park is just ahead at the foot of the hill.

Chester Walk 2.5 miles

  • From the Village Green on Route 11 head West,
  • the first street on the Right is Church St.
  • Turn Right and follow. After crossing the small bridge the is no sidewalk, so please keep to the left.
  • Cross the railroad and bridge over the Williams River,
  • At the fork turn Right to join Route 11.
  • Continue on Route 11 through the Stone Village crossing the Williams River toward Chester Depot.
  • Cross the railroad tracks and head up a small hill. As you start down hill stay to the right at the “Y” intersection.
  • Continue straight to the next intersection (Route 11) turn right and follow. The Village Green is 1/4 mile ahead on your left.


Moderate Hikes

Healdville Trail 5.8 miles R/T
The blue-blazed Healdville Trail climbs from the Parking area to Okemo Mountain’s 3,340 foot summit. The trail is 5.9 miles round trip offering a hefty half-day hike. Features along the trail include a fire tower and several lookouts which offer sweeping views of the local ski area. Crews from the Vermont Youth Conservation Corps constructed the Healdville Trail during the summers of 1991-1993.

Finding the Trail Head: From Ludlow Vermont, take VT Route #103 west towards Rutland. Approximately five miles from Ludlow on Route #103 turn left on Station Road (this turn is beside the Wright Construction Company building). Follow Station Road until you cross the railroad tracks. Turn left and there is a large parking area immediately at the end of a short drive.

The trail, blazed with blue paint, leaves the parking area and crosses two small brooks before ascending gradually along the second brook through a scenic hardwood forest. It runs gradually uphill and passes a vista point at 2.5 miles where a fine view of Mt Holly and the main Green Mountain chain can be seen on good viewing days. At 2.8 miles, the trail ascends steeply to a small clearing which was the site of the fire tower watchman’s cabin. The only remaining structure on the site is the chimney. Just after the cabin site the trail merges with a work road which runs from the end of the Okemo Mountain Road to the fire tower. The fire tower has been reconditioned by the State of Vermont and is open to hikers. The tower affords excellent views of the White Mountains to the northeast including Mt Washington, the Green Mountains North and South. To the east is Ascutney, and beyond is Manadnock in New Hampshire.

Weathersfield Trail 5.8 miles R/T

  • Hiking Time: 4.5 Hours
  • Vertical Rise: 2250 ft.
  • Rating: Strenuous

From the east: exit 8 off I-91: drive 3.3 miles to a right turn (North) onto Cascade Falls Road.

From the west (Ludlow): Take Route 131. Two miles east of the intersection of RT 106 you will climb a steep hill. As soon as the road begins to descend, watch for the black “Weathersfield Trail” sign. Turn left onto Cascade Falls Road.

Once on Cascade Falls Road, Bear left at the fork to a right turn at 3.6 miles. Follow up a short steep hill to the Ascutney State Park parking area.

From the information board, take the blue-blazed Weathersfield Trail which ascends log stairs as it enters the woods.

The trail winds, rises, and falls over varied terrain to the 1.3 mile mark where it levels slightly to cross the valley and meets an old roadway.

This is the white-blazed Old Weathersfield Trail, which you follow past Gus’s Lookout and a trail to the left that leads to the West Peak. Continue straight from this junction to the antennae-covered summit at 2.9 miles. Return to the junction and follow the same trail back to the parking area.

Aggressive Hikes

OVER the TOP 6.1 miles
Climb Ascutney Mountain (elevation 3,150), using the Weathersfield Trail located off RT 131, cross over the summit then descend via the Brownsville Trail to the parking area along RT 44.

  • Total distance: 6.1 miles; 4,500 Feet
  • Hike Time: 6 hours; Take time to plan carefully.
  • Vertical Rise: 4,500+ plus feet

NOTE: You will need 2 vehicles or arrange a drop off and pickup. Cell phone service is limited. A public phone is available at the general store in Brownsville: exit the RT 44 parking area and turn left; follow RT 44 to the Village, .5 miles.

START: From Rt 131 – 106 Junction, proceed east on Rt 131. Within two miles you will see Mount Ascutney in front of you. Rt 131 will then climb a hill. As soon at Rt 131 begins to descend watch for a black ” Weathersfield Trail” sign. Turn left onto Cascade Falls Road. Bear left at the fork to a right turn. Follow up a short steep hill to the parking area.

Take the blue-blazed Weathersfield Trail from the parking area. Reach Little Cascade Falls (.4 miles) Crystal cascade Falls (1.1 miles), then on to Gus’s Lookout and West Peak Vista before reaching the summit observation tower (2.9 miles).

From the observation tower pickup the trail to Brownsville Rock (.2 miles), then to North Peak Lookout (.8 miles); follow to Knee Lookout (1.4 miles). There the trail descends steadily through a forest reaching the top of the old green granite quarry (2.2 miles). A steep trail follows around the quarry to an old road bed, then on to the Parking lot (3.2 miles) The parking lot is located on RT 44 approx .5 mile east of Brownsville.

White Rocks 3.4 miles R/T

  • Total Distance: round trip 3.4 miles
  • Hiking Time: 2.5 hours
  • Vertical Rise: 1450 feet

This unique geological feature is on the Long Trail. The trail head is located on Route 140 of Route 7 of 103. Turn onto Sugarhill Rd. (dirt) and follow to “Green Mountain National Forest Picnic Area at White Rocks.”

The Keewaydin Trail (Blue blaze) begins in the far end of the parking area. At the fork go right. At the Junction of the Long Trail, turn right and follow the white blazes to 3 rock cairns in a small clearing with a sign for the White Rock Cliff Trail (Blue blazes). The trail descends .2 miles to a view from the top of White Rocks Cliff. The blue blazes are marked on rocks at your feet and are difficult to see. Retrace you steps back to the parking area.

A strenuous climb with amazing views.

*Directions to White Rocks: From visitor information parking lot. Take a right onto Route 103 towards Rutland, go ~10.7 miles. Take a left onto Route 140 (East Wallingford) and follow Route 140 for 4.4 miles (watch for sign “narrow bridge”). Take a sharp left before the bridge. Go .05 miles and take a right into White Rocks parking area.

Long Trail / Appalachian Trail
The trail crosses through our region with access points located off Routes 11, 140, and 103. Hikers can enjoy day trips or overnights at the many shelters along the way. A copy of the appropriate guide book can be obtained at area book stores and country stores near the trails.

More Summer Sports & Recreation > Hiking & Walking

Black River Action Team

Address: 101 Perley Gordon Rd
Springfield, Vermont 05156
Phone: (802) 885-1533

Green Mountain Hike and Dine, LLC.

Address: 72 Barker Road
Ludlow, Vermont 05149
Phone: (802) 558-2766

My Fitness Recovery

Address: PO Box 215
8 High St.
Ludlow, Vermont 05149
Phone: (802) 259-3617

The Good Farm

Address: 492 Rod and Gun Club Road
Ludlow, Vermont 05149
Phone: (802) 245-4746

Vermont Outdoor Guide Association (VOGA)

Address: P.O. Box 10
N. Ferrisburg, Vermont 05473
Phone: (802) 425-6211

Viking Nordic Center

Address: 615 Little Pond Road
Londonderry, Vermont 05148
Phone: (802) 824-3933