The best walks and hikes around Brattleboro

The Anne Stokes Loop Trail offers a delightful blend of forest scenery and intriguing history within the Madame Sherri Forest. As you hike, you'll traverse diverse terrain, from gentle woodland paths to some steeper, rocky sections, passing a small pond and winding through a hemlock forest. The route provides picturesque views of the surrounding area and Wantastiquet Mountain from higher elevations, making it a great option for those seeking natural beauty without an overly strenuous climb.

Planning your visit is straightforward, as the trail is well-worn and clearly marked with white blazes. While generally considered an easy hike, some rocky areas can be slick, especially in wet weather, so sturdy footwear is a good idea. Dogs are permitted on the trail, provided they are leashed, and you should always pack out their waste. This circular route is particularly popular in autumn for its vibrant fall colors.

What truly sets this trail apart are the historical ruins of Madame Sherri's "castle," a unique landmark from the early 1900s. The impressive stone foundation and grand staircase are all that remain of her French-inspired summer home, offering a fascinating glimpse into the past. Beyond the ruins, you'll also enjoy views of Indian Pond, framed by the open ledges of Mine Ledge, adding to the trail's distinctive charm.

The Ann Stokes Trail to Indian Pond offers a delightful moderate hike, covering 1.5 miles (2.4 km) with 287 feet (87 metres) of elevation gain in about 45 minutes. You'll wander through peaceful hemlock and deciduous forests, passing the scenic Indian Pond, which is beautifully framed by the open ledges of Mine Ledge. The terrain varies from well-worn paths to rocky sections, so watch your footing, especially if it's wet.

This popular route starts near the Wantastiquet Trailhead, where you can also explore the intriguing ruins of Madame Sherri's "castle." Parking is available, but it's wise to arrive early, especially during the vibrant fall foliage season when the area draws many visitors. The trail is well-marked and easy to follow, making it a straightforward outing.

Beyond its natural beauty, the trail is steeped in local history, winding through the Madame Sherri Forest, a land donated by Ann Stokes. This connection to a larger network of trails and the unique historical sites near the trailhead make it a standout option in the region, offering more than just a walk in the woods.

The West River Trail - Lower Section offers a delightful, easygoing escape along the West River in Southern Vermont. Following the historic bed of the former West River Railroad, this 1.8-mile (2.9 km) route is mostly flat, gaining only 59 feet (18 metres) in elevation, and takes about 45 minutes to hike. You'll enjoy continuous riverside scenery, winding through quiet forests of mixed hardwoods and wetlands, with a surface of packed earth and crushed stone that's gentle on your feet.

Accessing the trail is straightforward, with convenient trailheads located in Brattleboro near the Marina restaurant and in Dummerston on Rice Farm Road. This multi-use pathway is perfect for a leisurely stroll, a quick run, or a family outing, and dogs are permitted on leash. It's a great option for anyone seeking a peaceful outdoor experience without a strenuous climb.

Beyond its scenic beauty, the trail carries a rich history, tracing the path of the West River Railroad, once known as "36 miles of trouble." About a mile from the Marina Trailhead, you'll encounter the Riverstone Preserve, a unique area protecting a floodplain forest and a rare ice-scoured riverine cobblestone ecosystem. This section highlights the trail's natural and historical significance, offering more than just a walk in the woods.

If you're seeking a rewarding hike with stunning panoramas, the Mine Ledge Trail delivers. This moderate 1.8-mile (2.9 km) route climbs 703 feet (214 metres) over approximately 1 hour and 9 minutes, leading you through varied forest terrain. You'll navigate singletrack paths and old cart roads, with the highlight being the dramatic Mine Ledge viewpoint, offering sweeping vistas of Brattleboro, Vermont, and the Connecticut River.

Plan your visit by heading to the Wantastiquet Trailhead, often found near the historic Madame Sherri House ruins, where parking is typically available. The trail is dog-friendly, though you should be ready to leash your companion as needed. It's a great option for a relatively quick outing, but be prepared for some steep sections on the ascent.

This trail is part of the larger Wantastiquet-to-Monadnock Greenway, connecting you to a broader network of trails and natural features. The area is known for its diverse wildlife and offers a blend of natural beauty and historical intrigue, making it a notable destination in Cheshire County, New Hampshire.