Best attractions and places to see in Windham County include a diverse array of natural features, historical sites, and cultural points of interest. This Vermont region is characterized by its mountainous terrain, including summits like Mount Olga and Black Mountain, and significant river systems such as the Connecticut and West Rivers. Visitors can explore numerous covered bridges, historic districts, and state parks, offering opportunities for outdoor activities and cultural immersion. The area provides a blend of scenic landscapes and historical…
Last updated: April 24, 2026
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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.
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Mount Olga stands just 2,415 feet (737 m) tall, but still offers grand views over the surrounding landscape — especially if you climb the fire lookout tower at the summit.
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You park near the marina at the southern end of Spring Tree Road in a large gravel lot by the river. From here you follow the river north on the road to where it quickly becomes a bike path.
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The trees part to make way for outcroppings of stone at the summit which offer great views of the forest and north Brattleboro.
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You can park up off of Rice Farm Road. Parking is limited, but the trail is beautiful and includes many water features.
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The top of Stratton Mountain supports a fire lookout tower that is on the National Register of Historic Places. As you might imagine, the views from up here are great.
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From the top of this mountain you are close to the ski resort "L'Ermitage". You also have exceptional views, especially on the Harriman Reservoir.
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A lot of activities are possible in this little state park near Londonderry. It includes hiking, non-motorized boating, fishing, picnicking, wildlife watching, as well as winter sports.
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Windham County is rich in natural beauty. You can visit Lowell Lake for hiking and wildlife watching, or experience the picturesque Hamilton Falls, which offers a refreshing pool in summer. For panoramic views, consider climbing Mount Olga or Haystack Mountain, which overlooks the Harriman Reservoir. The summit of Stratton Mountain and fire lookout tower also provides expansive 360-degree views of southern Vermont.
Yes, Windham County offers a deep dive into history. The Stratton Mountain and fire lookout tower holds historical significance related to the Long Trail. You can also explore numerous well-preserved covered bridges throughout the county, such as the Bartonsville, Green River, and West Dummerston Covered Bridges. The Rockingham Meeting House is a notable 18th-century landmark, and the Historical Society of Windham County in Newfane features the County History Museum and the West River Railroad Museum. For more historical context, visit the Historical Society of Windham County.
The region is perfect for outdoor enthusiasts. You can hike, boat, fish, and watch wildlife at Lowell Lake. The Green Mountain National Forest and Molly Stark State Park offer numerous hiking trails. Cycling is popular along the West River Trail — Spring Tree Road Trailhead and quiet country roads. The Connecticut and West River systems are ideal for paddling, swimming, and fishing. In winter, skiing and snowshoeing are popular at places like Stratton Mountain Resort.
Absolutely! Lowell Lake State Park is excellent for families, offering hiking, non-motorized boating, fishing, and picnicking. Livewater Farm is another family-friendly spot. Many of the natural areas and covered bridges are also suitable for family outings and gentle walks.
Windham County offers a variety of hiking trails, from leisurely strolls to challenging treks. You can find easy paths like the Haystack Mountain Trail, moderate options such as Stratton Mountain via Long Trail, and more difficult routes like the Stratton Mountain and Stratton Pond Loop. For more details on hiking routes, explore the Hiking in Windham County guide.
Yes, cycling is a popular activity. The West River Trail — Spring Tree Road Trailhead provides access to a scenic path along the river suitable for cycling. For road cycling, you can find routes like the Lyons Pond – The Mill Pond loop. Gravel biking is also an option, with routes such as the Halifax Village Center – Green River Covered Bridge loop. Discover more routes in the Road Cycling Routes in Windham County and Gravel biking in Windham County guides.
Windham County offers attractions year-round. Summer is ideal for water activities at Hamilton Falls and hiking. Fall brings spectacular foliage, making it a popular time for scenic drives and walks. Winter transforms the region into a snowy paradise, perfect for skiing and snowshoeing at places like Stratton Mountain Resort. Spring offers a quieter experience with budding nature.
For grand vistas, head to the summits. Stratton Mountain and fire lookout tower offers 360-degree views, and you can climb its restored fire tower. Mount Olga also provides expansive views from its fire lookout tower. From the top of Haystack Mountain, you can see the Harriman Reservoir. Additionally, reaching the top of Ball Mountain Dam provides amazing views, including the Stratton Ski Resort.
Beyond the natural beauty, Windham County features several unique man-made landmarks. The Ball Mountain Dam is a significant structure offering impressive views from its summit. The historic Stratton Mountain and fire lookout tower is another notable landmark. The region is also known for its numerous picturesque covered bridges, which are prominent historical structures.
While many visitors flock to the major peaks, exploring the historic districts like the Bellows Falls Downtown Historic District or the Brattleboro Downtown Historic District offers a glimpse into the region's architectural heritage. The Newfane Village Center, recognized as a historic district, is known as one of Vermont's most photographed villages. You can also visit the West River Railroad Museum in Newfane for a unique historical perspective.
Yes, Hamilton Falls is a picturesque spot where you can enjoy a pool under the waterfall, ideal for cooling off in summer. The Connecticut River and West River systems also offer many hidden coves suitable for swimming.


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