The best family-friendly hikes and walks in Rutland County

This is a great family-friendly spot, and only one mile from the parking lot via trail. A knob of smooth Vermont bedrock rises over Route 4, granting panoramic views south to Mount Killington and the surrounding peaks. Great spot for a picnic!

Traverse Giorgetti to the park boundary near Rocky Pond on a singletrack, to avoid the eroded old pond road. You will be inspired to explore the great views, especially at Stegosaurus entrance overlooking the pond.

Spanning 325 acres, this haven boasts 17 miles (ca. 27 km) of top-notch single-track trails. Ideal for mountain biking, and other outdoor sports in central Vermont. Explore old logging roads amid stunning forests and scenic vistas.

Stratton Mountain is one of the most iconic peaks on the Long Trail, but not for its height, but rather for its historical significance. It was here in 1909 that James P. Taylor first imagined a “footpath in the wilderness,” which eventually became the Long Trail. The summit is forested, but a restored fire tower (that you can climb!) offers expansive 360-degree views of southern Vermont and the surrounding peaks. Today, Stratton is also home to a major ski resort, but the Long Trail bypasses the commercial slopes, staying on a quieter, wooded path. A nearby shelter, Stratton Pond Shelter, provides a peaceful overnight spot, just a short hike from the summit. This is a pretty built-up shelter (especially in comparison to the more common, simple three-sided lean-tos) so it's worth checking out even if you're not spending the night.

The Long Trail, the oldest long-distance hiking trail in the United States, begins at the Massachusetts–Vermont border near Williamstown, MA. This southern terminus is marked by a large wooden sign and lies at the junction where the Appalachian Trail (AT) continues and the Long Trail (LT) begins. The first 105 miles of the LT coincide with the AT before the two trails split at Maine Junction near Killington, VT. There are two primary approaches to reach the southern terminus: Via the Appalachian Trail from North Adams, MA: This route is approximately 3.8 miles and begins at Route 2 in North Adams, or via the Pine Cobble Trail from Williamstown, MA: This 3.3-mile trail starts at Pine Cobble Road in Williamstown and offers a scenic ascent to the LT's starting point. Both approaches take hikers to the VT/MA border, where the Long Trail officially begins its 272-mile journey northward through Vermont's Green Mountains to the Canadian border.

The Kent Brook Trail is a straightforward loop trail that takes you through a beautiful part of Gifford Woods State Park. The Appalachian Trail cuts through the middle of the loop.

Gifford Woods State Park is a popular destination for outdoor enthusiasts and Appalachian Trail through-hikers. The park has a wooded picnic area, two camping loops with water and restrooms, and one of Vermont's few remaining old-growth hardwood tree stands. The stand is home to grand-sized trees like sugar maple, beech, yellow birch, white ash, and hemlock, and the park's understory is rich with beautiful native wildflowers.

Gifford Woods State Park is a popular destination for outdoor enthusiasts and Appalachian Trail through-hikers. The park has a wooded picnic area, two camping loops with water and restrooms, and one of Vermont's few remaining old-growth hardwood tree stands. The stand is home to grand-sized trees like sugar maple, beech, yellow birch, white ash, and hemlock, and the park's understory is rich with beautiful native wildflowers.