The 5 Most Amazing Peaks in Windham County

Stratton Mountain, at 3,940 feet, is the highest peak in Windham County, Vermont. It holds historical significance as the place where the idea for the Long Trail and Appalachian Trail originated. The summit features a renovated 70-foot fire tower, offering breathtaking 360-degree views of the Green Mountain range and Taconic Mountains. You can find more details about its historical fire lookout tower on its highlight page: Stratton Mountain and fire lookout tower.

Yes, several peaks in Windham County feature fire lookout towers that provide expansive views. Stratton Mountain has a 70-foot fire tower with 360-degree views. Similarly, Mount Olga, located within Molly Stark State Park, also has a fire watch tower at its summit, offering grand views over the surrounding landscape, including the southern Vermont Green Mountains, the Berkshires, and Mount Monadnock.

Haystack Mountain is renowned for its rugged beauty and wide, complete panoramic views from its summit. You can expect exceptional vistas, especially of the Harriman Reservoir, and from certain locations, views extending to Mount Ascutney and Mount Monadnock in New Hampshire. The trails to the summit are generally moderate to difficult with steep sections.

The best time to visit depends on your preferred activities. For hiking and scenic chairlift rides, summer and fall offer pleasant weather and vibrant foliage. Winter is ideal for skiing and snowboarding at resorts like Mount Snow and Stratton Mountain. Spring can be muddy on trails due to snowmelt, but late spring (mid-June to mid-July) is spectacular for viewing the mountain laurel in bloom around Snow Hill in Connecticut.

Yes, there are family-friendly options. While some peaks like Haystack Mountain have moderate to difficult sections, the Mount Olga Trail is a moderate 1.7-mile loop hike suitable for families, leading to the fire tower. Additionally, the Nipmuck State Forest near Snow Hill in Connecticut offers over 9,000 acres with various hiking trails that can be enjoyed by families. Ekonk Hill also offers family-friendly activities at its turkey farm.

Haystack Mountain in Wilmington, Vermont, is noted for being dog-friendly, especially during winter for snowshoeing. Many trails within the Green Mountain National Forest, which encompasses peaks like Stratton Mountain and Haystack Mountain, generally allow dogs, but it's always advisable to check specific trail regulations and leash requirements before you go.

Beyond hiking, Windham County offers a variety of outdoor activities. You can find easy hikes like the Haystack Mountain Trail or Pinnacle at Windmill Hill Loop. For cycling enthusiasts, there are numerous routes for gravel biking and road cycling. For example, you can explore gravel biking routes from Stratton Mountain or road cycling loops around Lyons Pond. You can find more details on these activities in the guides for easy hikes, gravel biking, and road cycling routes in Windham County.

Snow Hill, the highest point in Windham County, Connecticut, is located within the Nipmuck State Forest. Its main draw is the Connecticut Mountain Laurel Sanctuary along Snow Hill Road. This sanctuary is particularly spectacular from mid-June to mid-July when the state flower is in full bloom, offering a serene natural experience through its scenic drives and walks.

Yes, Windham County is home to prominent ski resorts. Stratton Mountain operates as a major ski and snowboard resort in winter, while Mount Snow is a significant four-season resort known for its diverse terrain across four mountain faces, offering skiing and snowboarding for all abilities. Both also provide hiking and other activities during warmer months.

Black Mountain is a summit where the trees part to reveal outcroppings of stone. These natural clearings offer great views of the surrounding forest and north Brattleboro, making it a rewarding spot for hikers seeking scenic vistas.

Stratton Mountain is famously where the idea for both the Long Trail and the Appalachian Trail originated in 1909, envisioned by James P. Taylor. The summit's fire lookout tower, originally built in 1934 by the Civilian Conservation Corps, is also on the National Register of Historic Places, adding to its historical importance.

Yes, Windham County features several areas with conserved land and extensive trail networks. The Putney Mountain area, for example, offers over 800 acres of conserved land with around 15 miles of hiking trails along the Windmill Hill Ridgeline. Much of Haystack Mountain is also within the Green Mountain National Forest, providing numerous hiking opportunities.