Windham County is a region characterized by diverse landscapes, including extensive forested lands, picturesque river valleys, and rolling hills. Its varied terrain, from the iconic Stratton Mountain to the Connecticut and West River systems, provides a setting for outdoor pursuits. The area supports several sports like hiking, jogging, road cycling, mountain biking, and more, with extensive trail networks and natural features. This commitment to natural preservation ensures accessible outdoor recreation across its varied ecosystems.
Windham County offers a wide array of outdoor activities, with more than 100 routes available across several sports like hiking, jogging, road cycling, mountain biking, and more. Hikers and joggers can explore countless trails winding through forests and hills, ranging from gentle walks to challenging climbs, as detailed in the Hiking in Windham County guide. Cyclists find a paradise of quiet country roads and scenic byways, with rolling hills providing varied terrain for road cycling routes. Mountain bikers can discover trails for all skill levels, from smooth paths to technical single-track adventures, with options explored in the MTB Trails in Windham County guide. More than 2,000 visitors have shared their experiences on these routes, resulting in an average rating of 4.84 out of 5 stars.
96
Routes
4.8
(41)
Average rating
696
People visited

5.0
(1)
18
hikers
17.6km
05:25
610m
600m
Hard hike. Very good fitness required. Easily walkable paths.

12
hikers
3.31km
00:59
0m
280m
Easy hike. Easily walkable paths.

5.0
(1)
11
hikers
5.63km
01:38
160m
120m
Easy hike. Easily walkable paths.

7
hikers
5.60km
01:59
510m
0m
Moderate hike. Good fitness required. Easily walkable paths.
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4
runners
6.19km
01:04
290m
290m
Hard run. Good fitness required. Sure-footedness, sturdy shoes and alpine experience required.

9.74km
01:00
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces.

3.90km
00:26
80m
80m
Easy run. Mostly paved surfaces.

8
runners
9.18km
01:13
330m
330m
Hard run. Very good fitness required. Mostly paved surfaces.
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21.1km
02:06
430m
430m
Moderate mountain bike ride. Good fitness required.

3
riders
38.1km
03:40
700m
700m
Moderate mountain bike ride. Good fitness required.

2
riders
57.9km
04:58
980m
980m
Hard mountain bike ride. Very good fitness required.
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13
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces.

14
riders
127km
09:01
2,560m
2,560m
Hard gravel ride. Very good fitness required. Mostly paved surfaces.

10
riders
46.0km
03:16
940m
940m
Hard gravel ride. Very good fitness required. Mostly paved surfaces.

13
riders
71.9km
05:04
1,430m
1,430m
Hard gravel ride. Very good fitness required. You may need to push your bike for some segments of this route.
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5.0
(1)
10
riders
48.2km
02:18
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(1)
20
riders
31.7km
01:27
390m
390m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

6
riders
73.6km
03:51
1,300m
1,300m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(1)
7
riders
40.6km
02:00
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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7
riders
26.0km
01:59
330m
330m
Moderate bike ride. Good fitness required. Mostly paved surfaces.

6
riders
24.8km
01:40
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces.

5.0
(2)
6
riders
33.5km
02:07
420m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces.

4
riders
25.1km
01:42
320m
320m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
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Windham County offers a range of outdoor activities including Hiking, Jogging, Road cycling, Mountain biking, Touring cycling, and Gravel biking. The region features diverse landscapes with extensive trail networks for various skill levels. Over 170 routes are available across these sports.
Windham County provides numerous hiking trails through forests and hills, from gentle walks to challenging climbs. Notable areas include paths leading to Stratton Mountain and trails around Lowell Lake. More information is available in the Hiking in Windham County guide.
Yes, Windham County offers trails suitable for beginners and those seeking less strenuous options. These include gentle walks through various natural settings. Consult the Easy hikes in Windham County guide for specific routes.
Road cyclists can explore miles of scenic trails and quiet country roads with rolling hills. The region offers moderate and hard bike routes, often on paved surfaces. Details on routes can be found in the Road Cycling Routes in Windham County guide.
Windham County caters to mountain bikers of all skill levels, from smooth rail-trails to technical single-track adventures. Trails feature varying difficulty levels and elements like bermed corners and rock features. The MTB Trails in Windham County guide provides more information.
The county is characterized by extensive forested lands, picturesque river valleys, and upland streams. Key features include Stratton Mountain, the Connecticut River, West River systems, and Lowell Lake. These areas support diverse ecosystems and wildlife.
Stratton Mountain features a restored fire tower that offers expansive 360-degree views of southern Vermont and surrounding peaks. Other trails throughout the county provide various scenic overlooks of the diverse landscapes.
Windham County routes are popular among outdoor enthusiasts. There are more than 170 routes available, with over 2,400 visitors having shared their experiences. The routes have an average rating of 4.84 out of 5 stars.
Komoot offers several guides for Windham County, including Hiking in Windham County, Easy hikes in Windham County, and MTB Trails in Windham County. Guides are also available for running, road cycling, touring cycling, and gravel biking.
For general county-level information and planning efforts related to natural resources, the Windham Regional Commission is a key resource. Their official website is WindhamRegional.org, and they can be reached at (802) 257-4547.
The county's diverse ecosystems support abundant wildlife. Opportunities exist for birdwatching, including migratory birds like geese, swans, loons, and eagles, particularly along rivers and lakes. Deer, wild turkeys, and black bears can also be spotted on forest trails.

