Windmill Hill Ridgeline Trail System

Vermont trail highlights: Seven trails to visit on Windmill Ridge and surrounding land

The forested trail system, part of which extends off the ridgeline, spans the towns of Grafton, Athens, Rockingham, Westminster, Brookline, Putney, and Dummerston from north to south.

Visitors will be rewarded with magical fern-filled trails, old stone walls tucked into woodland, as well as stunning views. But, it’s not just people who enjoy the land; it offers great habitat for  animals that need to roam, including bobcats, moose, and bear.

There are so many trails, it’s hard to know where to start. Here we highlight some trail routes, each of varying length and difficulty. They are organized from north to south.

We hope you get inspired to discover these and the many other Vermont trails along the ridgeline.

1. Creature Rock Trail at Athens Dome

Who doesn’t want to take a trail called Creature Rock? What will you find?

From the parking area at the upper end of the drivable part of Ledge Road in Grafton (northwest of the ridgeline), you’ll first find a map at a kiosk.

From there, the moderate-level trail, called Creature Rock Trail, follows white markers up a curvy set of log steps up the hill into the woods. The trail then climbs west at a steady grade up through mature hardwood forest.

At about 0.2 miles you’ll come across Creature Rock, a pile of large boulders surrounded by scraggly trees.

Take a moment to wonder at a house-sized pile of rock

Creature Rock’s name comes from a previous owner’s children who heard animal sounds from within the rock crevices, so have a listen too!

If you continue on, the trail bears right and continues west up to a junction.

Here, a short 0.1-mile yellow-blazed spur trail leads north uphill where there is a camping shelter and a limited, east-facing vista overlooking Cambridgeport and Atcherson Hollow below.

Back at the junction, Creature Rock Trail continues west across and down the slope to another trail junction (this one might be labeled junction #16 on some maps). From here, it’s possible to either continue several miles west to Bear Hill, or to make a loop by turning left and rejoining Ledge Road (see map). Of course, you can also return the way you came.

2. Dunn Nature Trail, an easy-to-moderate family friendly hike

The Stephen Martin Memorial Wildlife Sanctuary is a lovely place to find peace and quiet, and explore nature.

It’s located in the northwest corner of Westminster, Vermont.

Visitors arriving at the parking area on Bemis Hill Road will find a 1.1-mile lollipop-loop called the Dunn Nature Trail.

Informational brochures are available at the trailhead kiosk (pictured). The trail, marked with blue discs, has 14 numbered signposts as part of an interpretive trail. Signposts identify natural features, including rich woodlands and a historic lime kiln.

Here you’ll find ferns, frogs, and peaceful old woods

There is a majestic stretch of forest that has remained undisturbed for a long time. Look close and you might find uncommon fern species and two springtime pools, which are important to amphibians for breeding.

From the parking lot, the occasionally rugged trail crosses the hilly, forested landscape. However, there are several short, steep sections and rocky outcrops to navigate and the trail crosses a small stream on stones.

Please note that dogs, bicycles, and hunting are not allowed in the sanctuary and that the trailhead is not plowed in winter.

The land was originally received as a bequest to The Nature Conservancy from Sarah Ann Martin in memory of her brother Stephen Martin who was killed in WWI. Later it was conveyed to the Windmill Hill Pinnacle Association, which manages it today.

3. The Pinnacle: Two options to reach stunning views

A very popular Vermont trail heads to The Pinnacle summit (1,683 feet). Here, the ridgeline runs along the Brookline–Westminster line. From the top you can look out onto Hedgehog Gulf, Mount Snow, and Stratton Mountain.

There are multiple trails to the summit, so we are highlighting two options: a moderate approach and a difficult one.

Option one: A moderate-level, 4-mile lollipop route to the summit of The Pinnacle

This route follows wide and narrow trails up and over the summit. It combines sections of three primary trails and provides an excellent sampling of all the ridge has to offer. The trails are very well marked and easy to follow.

At the Pinnacle Trailhead (1026 Windmill Hill Road North, Westminster) pass through the old, ornate metal gate. Follow the red-disc-blazed Holden Trail, which heads west and southwest into the woods.

It climbs at a gentle grade, occasionally passing over exposed bedrock outcrops.

At a junction near the crest of a sub-ridge, about a half-mile in, take the blue-disc-blazed Headwaters Trail.

The trail is narrower and winds around the slope, passing a stone wall and descending to cross the headwaters of Sacketts Brook. It then climbs at a moderate grade for about half a mile up to the crest of Windmill Ridge.

At the end of this trail, turn right and follow the white-blazed, main Ridgeline Trail (pictured) 1.3 miles north to the top of The Pinnacle (note that this stretch of Ridgeline Trail is called Pinnacle Trail on some maps). The trail rolls along the spine of the ridge, gradually rising as it goes. Just below the summit, sedges cover the ground surrounding the trail beneath a woodland canopy of oaks and hop hornbeam trees.

At the open summit of The Pinnacle, there is a hiker’s cabin and a west-facing vista with rock benches.

From the summit, follow Holden Trail southeast down the ridge. Back at the junction with Headwaters Trail, turn left to descend back to the trailhead and parking lot.

Option two: A difficult, but rewarding, route to the summit of The Pinnacle

This challenging climb to The Pinnacle starts on the western side of the summit at a small parking area located at 1200 Grassy Brook Road in Brookline.

Starting from the map kiosk near the parking lot, take the Radford-Smith Trail, which immediately dips into dark hemlock woods and crosses Grassy Brook (pictured) on a sturdy wood-and-iron bridge.

From there, the trail climbs steeply through well-graded switchbacks for about half a mile to a stone wall and large old tree with spread limbs.

Then it goes north across the slope at a mostly level grade for another half mile or so and ends at a junction with the Cascade Trail.

Heading east (right) the Cascade Trail  meanders for 0.8 miles up the rest of the way to the crest of the ridge. It passes through a stand of large oak and ash trees along the way.

At a junction with the main Ridgeline Trail (on some maps this will be called Pinnacle Trail), it’s just another few hundred feet north through a breathtaking savannah-like woodland to the open summit ledge of The Pinnacle.

Round trip, this route is about 4 miles.

4. Putney Mountain summit: A popular family friendly hike

This hike takes visitors along a north-south running ridgeline (separating Putney and Brookline) to the summit of Putney Mountain (1,667 feet). Note that it’s a very popular destination, and can be crowded.

The summit, which is kept open through management that includes sheep grazing, offers fantastic views east and west from several rock outcrops.

The shortest route is an out-and-back option

The shortest route (1.2 miles) is to climb the summit by taking the Ridgeline Trail, pictured, out and back. This trail departs from the main parking area at 443 Putney Mountain Road near the Putney–Brookline town line.

This route follows the Ridgeline Trail north from the trailhead, rolling along the ridge but gradually gaining elevation as it goes.

The trail is well-graded, featuring several easy-to-navigate rock ledge scrambles.

In several places, this wide and well-used trail braids–or splits–onto two branches that eventually rejoin, but it is easy to follow.

A slightly longer route is called Nature Trail Loop

If you prefer to see new terrain throughout your hike, you can get to the summit from the main parking area (443 Putney Mountain Road) by doing a 1.4-mile loop.

Start by taking the Ridgeline Trail to the summit.

Instead of returning to the parking area by backtracking, take a short linking trail that descends from the summit to the west to a junction with the southern part of the West Cliff Trail, pictured. This loop is also known as the “Nature Trail”.

5. Libby's Way, an easy trail though ridgeline forest

The Libby’s Way trail beckons visitors to Hinton Woods, which connects Putney Mountain with the the Silvio O. Conte Wildlife Refuge and the Dine Trail to the south. (Note that on some older maps it may be called the Hinton Trail.)

This 0.7-mile easy trail starts from the Putney Mountain Trailhead parking lot at 443 Putney Mountain Road, near the Putney–Brookline town line. Unless you want to extend your hike to additional trails, this is an out-and-back hike.

The wide trail gently rolls along or near the crest of the ridge south of Putney Mountain. It passes through hardwood forest and crosses two small streams. Halfway along, the trail comes near an old stone wall in a scenic, fern-filled woodland glade.

Most of the trail follows an old woods road, though it narrows to a hiking trail for a short stretch at the southern end.

6. The Dine Trail: an easy woodland walk in south Putney

At the far southern end of Putney, near the Dummerston line, there are several trails that can be hiked as out-and-back or combined to make more challenging loops.

The 1.5-mile Dine Trail, marked with white discs, is a relatively easy trail that runs north-south along the ridge crest south of Putney Mountain. There is a small parking lot at 478 Holland Hill Road.

While there are no scenic views or vistas, the trail passes through pleasant woodland settings with occasional stone walls, rock outcrops, and wolf trees that suggest the land’s former open pastures. It traverses Putney Mountain Association land, conserved with VLT, and the Silvio O. Conte Wildlife Refuge.

7. The Hannum Trail: a moderately challenging forest hike that can be easily combined with other trails

The moderately difficult Hannum Trail runs roughly parallel to the Dine Trail. As with the Dine Trail, the northernmost part of the this route is on Silvio O. Conte National Wildlife Refuge land while the southern half is on Putney Mountain Association land.

Park at a small pull-off area at 442 Holland Hill Road, Putney. From there the this 1.4-mile trail passes through a variety of wooded habitats, including pine stands, hardwood forest, and regenerating areas. There are attractive fern glades, rugged rock outcrop ledges, and old stone walls along the way, and one stream crossing on a small wooden bridge.

The trail is marked with yellow discs.

Upping your mileage with the Dine, Hannum, and Beaver Pond Loop Trails

The Dine and Hannum trails can be combined to form a moderately difficult 3-mile loop hike starting from either of the trailheads along Holland Hill Road.

Near the junction of these two hiking trails you could also add the 1.6-mile Beaver Pond Loop trail, which traverses the Wildlife Refuge land, has relatively little elevation gain, and includes several scenic wetlands along the western half of the loop. Please note that the eastern half is an old woods road that is moderately eroded in places.