Moderate and gently graded, this hike is filled with natural history wonders, stone walls, and ancient foundations to explore. The route passes through some beautiful open maple groves and emerges on the 1,683-foot summit with wide-open views to the west and a stone overnight shelter. The land is owned by the Windmill Hill Pinnacle Association, which has protected more than 1,800 acres of land stretched out over this 20-mile ridge in southeastern Vermont and is one of many small community-based land trusts in New England preserving land for wildlife, conservation, and recreation.

From the Holden Trailhead, head west past the artistically inspired iron gate. Proceed up Holden Trail for 0.5 mile past some fine examples of colonial farmhouse foundations, abandoned wells, and stone walls. You will also spot many large wolf trees along the way. Turn right at the first trail intersection and continue up Holden Trail. The trail begins to climb a bit here, but never too steeply. Near the summit, the path cuts through a fine mature maple grove with an open, grassy understory. This rare grove likely evolved this way as the result of a single wolf tree. Only sedges and grasses grow below the maples now, and the wide-open forest understory is a rare and beautiful sight.

After 0.9 mile, turn left on Pinnacle Trail; your destination is just ahead through the trees. The trail emerges onto the Pinnacle, a gorgeous open summit with a stone and timber overnight shelter. Kids will have a blast exploring the shelter and climbing up to the large sleeping loft. The shelter is free to stay in and open to the public, but reservations through the Windmill Hill Pinnacle Association are required. Soak in the views and the sunshine—you can see five different ski areas and many of Vermont’s highest peaks from here. See if you can spot them all.

Return the way you came for a 3.0-mile round-trip.

Green Mountain Orchards at 130 West Hill Road in Putney is a great place to pick up fresh apples, pick your own blueberries, eat some cider doughnuts, or go for a hayride. Also nearby are the rock slides and pools of Pikes Falls in nearby Jamaica (see Trip 51).
 

Putney has a great selection of restaurants and delis, and even a not-to-be missed barbecue joint. The historic and newly rebuilt Putney General Store, first built in 1769, offers excellent sandwiches and picnic fare. Stop by Curtis’ BBQ on US 5 to enjoy live music, a playground, and, of course, piles of barbecue served out of a blue school bus in a tranquil park-like setting.