Windsor County, a region in Vermont, features a diverse landscape ideal for outdoor activities. Its western parts rise into the Green Mountains, providing challenging terrain, while the eastern border follows the Connecticut River valley, offering gentler routes. This varied geography, including several rivers like the White and Ottauauquechee, supports a range of outdoor pursuits such as hiking, jogging, road cycling, touring cycling, and more. State parks and forests further enhance opportunities for exploration in Windsor County.
143
Routes
4.6
(130)
Average rating
1540
People visited

1
hikers
4.46km
01:11
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

3
hikers
1.67km
00:36
150m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

3
hikers
7.30km
02:05
180m
180m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

3
hikers
5.04km
01:23
70m
100m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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9
riders
66.3km
02:55
620m
620m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

3.0
(1)
53
riders
101km
04:29
1,010m
1,010m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(1)
32
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

26
riders
27.9km
01:15
300m
300m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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9
runners
7.14km
01:15
530m
530m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

6
runners
9.42km
01:16
270m
270m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.05km
00:33
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

42
runners
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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68
riders
19.1km
02:03
570m
570m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

44
riders
11.2km
01:03
220m
220m
Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

21
riders
23.3km
02:21
600m
600m
Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.

13
riders
29.0km
02:42
560m
560m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
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5.0
(3)
17
riders
30.0km
02:03
180m
180m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

21
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
13
riders
42.2km
02:49
510m
510m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

10
riders
76.4km
05:04
1,120m
1,120m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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5.0
(1)
7
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
6
riders
79.5km
05:49
1,700m
1,700m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

7
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
6
riders
31.2km
02:14
640m
650m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Windsor County offers a variety of outdoor activities, including Hiking, Jogging, Road cycling, Touring cycling, Mountain biking, and Gravel biking. The region features diverse terrain from the Green Mountains to the Connecticut River valley. More than 370 routes are available for exploration.
Windsor County provides numerous hiking opportunities, ranging from gentle paths to challenging mountain ascents. Notable areas include Mount Ascutney State Park and sections of the Appalachian National Scenic Trail. A comprehensive overview of trails is available in the Hiking in Windsor County guide.
Easy hiking trails in Windsor County are available in various locations, suitable for beginners or those seeking less strenuous options. Areas like The Pogue in Woodstock offer accessible paths. For specific routes, refer to the Easy hikes in Windsor County guide.
Windsor County offers a range of cycling routes for both road and touring cyclists. The Connecticut River valley provides flatter terrain, while the Green Mountains offer more challenging climbs. Detailed routes can be found in the Road Cycling Routes in Windsor County and Cycling in Windsor County guides.
Yes, Windsor County features trails suitable for mountain biking and gravel biking. Mount Ascutney State Park alone offers over 35 miles of mountain biking trails. Information on these routes is available in the MTB Trails in Windsor County and Gravel biking in Windsor County guides.
Windsor County is home to several natural landmarks. These include Quechee Gorge, where the Ottauquechee River flows 168 feet (51 meters) below, and Mount Ascutney, which rises to 3,144 feet (958 meters). The region also features parts of the Green Mountains and the Connecticut River.
Windsor County hosts several state parks that offer outdoor recreation. These include Calvin Coolidge State Park, Ascutney State Park, Quechee Gorge State Park, and Camp Plymouth State Park. These parks provide access to hiking, biking, and other activities.
Windsor County offers opportunities for waterfall hikes, allowing visitors to explore scenic cascades. The region's rivers and varied terrain create several spots where waterfalls can be found. A dedicated guide for Waterfall hikes in Windsor County is available.
Windsor County offers various family-friendly outdoor activities, including easy hiking trails and scenic areas like Quechee Gorge. Many state parks provide facilities and accessible routes suitable for families. Options for less strenuous activities are available across the region.
Windsor County is a popular destination for outdoor activities on komoot, with more than 6,000 visitors having shared their experiences. The region's routes have an average rating of 4.65 out of 5 stars, indicating high user satisfaction.
For administrative inquiries related to Windsor County, the Windsor County Clerk's office can be reached at (802) 457-5211. The Town of Windsor also maintains an official website at windsorvt.org.
Yes, Windsor County offers various running trails suitable for jogging. These trails can be found in different settings, from river valleys to more wooded areas. The Running Trails in Windsor County guide provides detailed information on available routes.

