Windsor VermontHIKING TRAILS & PLACES TO HIKE


Listed below are the best hiking trails and places to hike near Windsor, Vermont.



1. Paradise Park

SCENIC FOREST AND LAKE


Paradise Park offers a lovely series of trails through mature forest, along streams, and around Lake Runnemede. Hikers can choose from multiple trail options ranging from an easy half-mile path to more challenging 5-mile loops with varied terrain. The park features numerous benches, picnic areas, and opportunities to spot wildlife including deer, fox, otter, beaver, and a wide variety of birds.


2. Mount Ascutney Futures Trail

SUMMIT CHALLENGE HIKE


The Futures Trail on Mount Ascutney offers a challenging 4.6-mile one-way hike to the summit. This trail provides hikers with a demanding but rewarding journey through the diverse ecosystems of one of Vermont's most prominent mountains. From the summit, hikers are rewarded with panoramic views of the surrounding countryside and Connecticut River Valley.


3. Windsor Trail

DIRECT SUMMIT ROUTE


The Windsor Trail provides a more direct 2.7-mile one-way route to the summit of Mount Ascutney. This moderate to difficult trail is popular with hikers looking for a shorter but still challenging ascent to the mountain's peak. Hikers on the Windsor Trail are treated to beautiful forest scenery and impressive views of the surrounding landscape once they reach the summit.


4. Brownsville Trail

HISTORIC MOUNTAIN PATH


The Brownsville Trail extends 3.2 miles one-way to the summit of Mount Ascutney. This moderately difficult trail winds through diverse forest environments and offers several scenic overlooks along the way. Hikers often appreciate the trail's historical significance as one of the original paths up this iconic Vermont mountain.


5. Weathersfield Trail

CASCADES AND VISTAS


The Weathersfield Trail offers a 2.9-mile one-way journey to Mount Ascutney's summit from the neighboring town. This moderate to difficult trail features beautiful Cascade Falls and passes through varied terrain including hardwood forests and rocky outcroppings. The trail rewards hikers with spectacular views and a sense of accomplishment upon reaching the mountain's peak.



6. Mount Tom and The Pogue Loop

HISTORIC PARK TREK


The Mount Tom and The Pogue loop is located in the Marsh-Billings-Rockefeller National Historical Park near Windsor County. This moderate trail combines woodland hiking with historical significance as hikers pass through one of Vermont's most celebrated national park properties. The loop features a picturesque pond (The Pogue) and offers excellent views of the surrounding Woodstock area from Mount Tom's summit.


7. Cross Vermont Trail

LONG-DISTANCE MULTI-USE PATH


The Cross Vermont Trail passes through Windsor as part of its ambitious route across the entire state. This multi-use trail offers hikers easy to moderate terrain suitable for various skill levels and connects numerous communities and natural areas. Hikers enjoy scenic river views, forested sections, and glimpses of historic New England landscapes along this well-maintained pathway.


8. South Barre Bike Path

ACCESSIBLE HIKING OPTION


The South Barre Bike Path, located near Windsor County, offers an easy hiking option on a well-maintained surface. This gentle trail is perfect for beginners, families with young children, or those seeking a more accessible outdoor experience. Hikers can enjoy the pastoral Vermont countryside and river views along this converted rail trail.


9. Ascutney Outdoors Center Trails

VARIED SKILL LEVEL PATHS


The Ascutney Outdoors Center hosts a network of trails suitable for hiking with difficulty levels ranging from beginner to expert. These multi-use trails wind through the former ski area property and surrounding forest, offering a mix of open views and woodland experiences. Hikers can customize their experience based on skill level and desired distance, making this an excellent option for various abilities.


10. Town Forest Trails

CHALLENGING FOREST EXPLORATION


The Town Forest Trails in Brownsville offer hikers a more challenging outdoor experience with intermediate to expert terrain. These trails wind through a protected municipal forest with diverse habitats and ecological features to explore. Experienced hikers appreciate the technical challenges and relative solitude these less-trafficked paths provide in the shadow of Mount Ascutney.