Hiking Trails - Walk Woodstock

Hiking Trails In and around Woodstock

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Woodstock is a walker's paradise. Anywhere in the village you can literally step outside your door onto an interconnected, compact system of pathways, trails, and carriage roads. They take you from the historic center of Woodstock, across meadows and woodlands, through a national park and up to scenic vistas overlooking valleys, villages, and rural countryside.

Take a day hike or a short stroll. Enjoy the rich conifer forests of Mount Peg, the historic core of Woodstock Village and its pedestrian pathways, Faulkner Park, Billings Park, the Vermont Land Trust's King Farm, and the historic carriage roads and paths of the Marsh-Billings- Rockefeller National Historical Park.

If you are seeking a more backcountry experience, the Appalachian Trail passes just north of Woodstock, and the Long Trail is not far away. There are several Appalachian Trail access points in and around Woodstock and access points to the Long Trail are less than an hour drive away.

Woodstock Hikes
Hikes starting from the National Park Visitor Center
Appalachian Trail Hikes

Recommended Hikes


Trail Name and Type




Starting-Ending Point


Mount Peg

The trail starts at the kiosk, and the trail will be fairly steep for a short section, but leads to a more gentle series of trails. Follow signs for the Summit Trail and make your way up to a grassy overlook. The bench at the overlook offers a wonderful place from which to enjoy the view of the Ottauquechee River Valley, the Billings Farm and Museum, and Mount Tom.

2.5 miles

Golf Street at the Mount Peg trailhead kiosk

Stewardship Trail

A half mile trail on easy terrain starts 100 yards from the Forest Center and leads to the Artistree Studio on Route 12. To reach the Forest Center cross the street from the Billings Park parking area and turn right onto Mountain Road. Follow Mountain Road for a tenth of a mile to the Forest Center.

1 mile

Route 12, Marsh-Billings-Rockefeller National Historical Park, Woodstock at the Forest Center

Poet's Trail

Through fields and woods follow the Poet's Trail to an overlook of the Ottauquechee River Valley below. At the farm you can see flocks of Guinea hens, an alpaca, pigs and goats. King Farm can also be accessed by the trails that connect it to the Marsh-Billings-Rockefeller National Historical Park.

1.5 miles

King Farm, Woodstock - park at the barns next to the white farm house. Trail starts behind the barns.


Faulkner Trail

An easy walk that switchbacks up to the South Peak of Mount Tom where you can enjoy a panoramic view of the Woodstock village and surrounding mountains. Near the top of South Peak the switchbacks stop and there is a lovely overlook and some benches. The last 100 yards of trail is more challenging, with rock outcrops and uneven footing. At the top, take in the breathtaking view of Woodstock village and the surrounding mountains.

2.75 miles

Faulkner Park, Mountain Road, Woodstock; the Faulkner Trail starts at the rear of the Park

Mountain Road to the Pogue

The Pogue is a man-made 14-acre pond tucked into the hills of the Park's Mount Tom Forest. You can reach the Pogue by way of Mountain Road, one of the park's historic carriage roads. Near the start of the hike you will encounter two unique structures, the Woodshed and the Forest Center. The Woodshed loft opens directly onto the Mountain Road and houses an exhibition of old carriages. The Walk Woodstock map shows you some alternate trails for your return trip.

2.5 miles

Route 12, Marsh-Billings-Rockefeller National Historical Park at the Forest Center

Mountain Road to South Peak

Head up Mountain Road, and after 1.1 miles take a left on Mount Tom Road. Follow the carriage road past several open pastures and over a beautiful stonework bridge to the South Peak summit. At the top take in a panoramic view of Woodstock, and rest a bit. You can retrace your steps to return to the Visitor Center, or take the One Less Traveled Trail, or North Peak Trail back to Mountain Road in order to see more of the forest.

4 miles

Route 12, Marsh-Billings-Rockefeller National Historical Park

Prosper Road to the Pogue and South Peak

This route to the Pogue and South Peak offer a more gradual hike, and a chance to explore the west side of the National Park. From the parking area take Prosper Trail, at the beginning of which you will cross a long bridge. Stay on Prosper Trail until you reach McKenzie Road; turn left to McKenzie Road, then right on North Ridge Loop, then right again at the bottom of the hill to the Pogue. Take a left and walk about a third of the way around the Pogue and picking up Mountain Road on the left; take that downhill to a right on Mount Tom Road, and follow that all the way to South Peak. Retrace your steps to return to the parking area, or alternatively take McKenzie Road instead of Prosper Trail.

4 miles

Prosper Road, Woodstock at the Prosper trailhead parking lot


North Peak

This trail can be taken as an alternate route to or from South Peak or the Pogue. It is a narrower woods trail that is parallel with Mountain Road until it takes a sharp turn to the southeast and leads to North Peak. The grade is not steep, but the footing is difficult at times. Beautiful views into the old-growth hemlock-hardwood forest.

4.2 miles to South Peak

2.5 miles to Pogue

Marsh-Billings-Rockefeller National Historical Park, off of The Mountain Road

Precipice Trail

For those seeking a more adventurous outing the Precipice trail is a rugged hike on the rocky southwestern side of Mount Tom. Much of the trail is only a small ledge on the side of a steep rock face. Do not attempt this hike in the rain or without sturdy footwear. To take another route back use your Walk Woodstock map.

1.2 miles

Marsh-Billings-Rockefeller National Historical Park, off of The Mountain Road



Trail Name and Type


Round -Trip Distances

Starting- Ending Point


Rt 12 to Mount Ascutney View (AT North)

Cross the bridge then climb south through a cow pasture and field. After entering the woods continue on a moderate incline to a view of Mount Ascutney to the south. You may choose to hike further; however there is no road access for several miles. Note: For hikers who seek a short experience on the AT with a nice view: Walk just the first .25 mile up the cow pasture to a beautiful view looking north.

2 miles

Route 12. Parking area 0.5 miles past North Bridgewater Road on the left

Stage Road to Pomfret Road (AT North)

Cross the small bridge to the right of the parking space. Note: Watch out for a very muddy section on this trail. You will cross two dirt roads before reaching Pomfret Road. (one of the smaller roads does not appear on the map). Be careful when crossing Pomfret Brook at the end of this section since there is no bridge.

4.4 miles

Stage Road. Parking area 0.5 miles after Suicide Six Ski Resort on the right

Stage Road to Routh 12

(AT South)

Cross Stage Road and walk up to Dana Hill. Beautiful view! It is a moderate climb for about 1 mile to the top of Dana Hill, a longer but more gradual climb than from Route 12.

3 miles

Stage Road. Parking area 0.5 miles after Suicide Six Ski Resort on the right

Pomfret Rd. to Cloudland Rd. (AT North)

Beautiful view and multiple stonewalls.

4 miles

Pomfret Road. Parking area 0.25 miles after Bartlett Brook Road on the left

Pomfret Rd. to Stage Rd. (AT South)

Brooks and stonewalls present. Less elevation gain than Pomfret Road to Cloudland Road.

4.4 miles

Pomfret Road. Parking area 0.25 miles after Bartlett Brook Road on the left


Route 12 to Stage Road (AT North)

Facing the display side of the kiosk, take the trail to the right from the parking lot. Cross Route 12 and climb up Dana Hill. There is about ½ mile of strenuous climbing to the top of Dana Hill. There's a beautiful view! You may choose to come back to the Route 12 trailhead or to continue to Stage Road.

3 miles

Route 12. Parking area 0.5 miles past North Bridgewater Road on the left

Appalachian Trailhead map

View of Woodstock from Mount Tom

View of Woodstock from Mt Tom

J Waite

Scenic views

Mount Tom's South Peak
South Peak offers the best view around! From the overlook you can enjoy panoramic views of Woodstock and the surrounding hills. There are several ways to get to South Peak, all exploring different parts of the Woodstock trails system.

View from Mount Tom Summit:
From west to east, in the foreground is the King Farm with Killington above it on the horizon. To the left is Route 4 and the high school as viewed up the Ottauquechee Valley. To the south, Mt. Ascutney is on the horizon. Below and still proceeding eastward, is the north end of Kendron Valley with the golf course, Vail Field and then the Woodstock Inn. To the left of the Inn is the Windsor County Court House and covered bridge, above which is visible the bald knob of Mt. Peg. Toward the east, the Congregational Church is in the foreground with Billings Farm situated north of the river and then the mountains of New Hampshire are on the horizon above it. The structure on the summit of Mount Tom displays a lighted star and cross with shines over Woodstock during the Christmas and Easter holidays respectively. (Woodstock Inn and Resort Hiking Map 1980)

Hike Details:

Mountain Road to South Peak (moderate)

Prosper Road to South Peak (moderate)

Faulkner Trail to South Peak (moderate)

North Peak Trail to South Peak (difficult)

Precipice Trail to South Peak (difficult)

Mt Peg Overlook

Mt Peg Overlook

Mount Peg Overlook

Mount Peg trails start right in town. A short hike leads to a beautiful clearing where you can view the Ottauquechee River Valley, the Billings Farm and Museum, and Mount Tom.

Hike Details:

Mount Peg Summit hike (easy)

King Farm Overlook

King Farm Overlook

King Farm Overlook

Poet's trail was inaugurated in 2012 and was part of a project of the Woodstock Union High School's AP English Class. Along the short trail you will encounter not only poetry, but also eclectic sculptures.

Hike Details:

King Farm Poet's Trail Hike

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