4.8
(56)
860
hikers
38
hikes
Easy hiking trails in Windham County, Vermont, traverse a landscape characterized by the rolling hills of the Green Mountains, dense forests, and numerous picturesque lakes. The region offers a variety of scenic experiences, from gentle lakeside paths to trails winding through lush woodlands. Hikers can explore a vast network of routes, many of which are suitable for beginners and families.
Last updated: April 26, 2026
16
hikers
3.31km
00:59
0m
280m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
11
hikers
5.63km
01:38
160m
120m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Sign up for free
3
hikers
3.91km
01:09
100m
100m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
3.48km
01:07
170m
100m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
4.34km
01:13
100m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2.91km
00:45
20m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
993m
00:18
50m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.6
(8)
46
hikers
5.16km
01:20
30m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(5)
24
hikers
2.85km
00:56
130m
140m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
19
hikers
4.34km
01:11
60m
60m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Windham County

Easy hikes around Brattleboro

Easy hikes around West Brattleboro

Easy hikes around Algiers

Easy hikes in Fort Dummer State Park

Easy hikes around West Dummerston

Easy hikes around Wilmington

Easy hikes around Chimney Hill

Easy hikes around Putney
Roundabout Brattleboro — a charming challenge in the New England countryside
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.
1
0
This family-friendly hike takes you all the way around the tranquil waters of Grout Pond, with a few jaunts through the forest too. There's just one problem: Mud. Bog bridges are in place to help you get through the worst of it, but waterproof footwear can be a big help on this sort of terrain.
1
0
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.
0
0
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.
0
0
This is a wonderful and very picturesque spot. In summer you can enjoy the pool under the waterfall with fresh water ideal for cooling off after the walk. Remember that it is not allowed to climb the waterfall and the surface of the stones is really slippery
1
0
It is worth reaching the top of the dam. The road in itself is a real pass. When you reach the top the views are amazing, until you get to see Straton Ski Resort
2
0
Windham County offers a wide selection of easy hiking trails, with 19 routes specifically categorized as easy. In total, there are 39 hiking routes across various difficulty levels in the region.
Yes, Windham County is an excellent destination for family-friendly hikes. Many easy trails are suitable for all ages, such as the Lowell Lake loop, which offers a relatively flat path around the lake, or the West River Trail - Lower Section, known for its gentle riverside landscapes.
Easy hikes in Windham County often feature diverse natural beauty, including rolling hills, dense forests, and tranquil lakes. You can find trails with panoramic vistas, such as the Pinnacle at Windmill Hill Loop, or enjoy lakeside scenery on routes like the Lake Raponda Trail. Many trails also offer views of the Green Mountains.
Yes, you can find easy hikes that lead to beautiful waterfalls. The Hamilton Falls via Ball Mountain Dam route is an easy option that takes you to the impressive Hamilton Falls.
Windham County offers several enjoyable easy loop hikes. The Pinnacle at Windmill Hill Loop provides scenic vistas, while the Lowell Lake loop offers a peaceful walk around the lake. Another popular choice is the Grout Pond Loop Trail, known for its tranquil setting.
The easy trails in Windham County are highly rated by the komoot community, with an average score of 4.8 stars from over 50 reviews. Hikers frequently praise the region's diverse natural beauty, well-maintained paths, and the peaceful atmosphere of its woodlands and lakeside routes.
Windham County offers beautiful hiking experiences year-round. Spring brings lush greenery, summer provides pleasant temperatures for forest walks, and autumn is spectacular with vibrant fall foliage. Even winter offers serene snowshoeing or cross-country skiing opportunities on many easy trails, though conditions should always be checked.
Yes, some easy trails offer views or access to the lower slopes of prominent peaks. For example, the Haystack Mountain Trail provides views from the lower slopes of Haystack Mountain. Additionally, the Mount Olga Trail offers an accessible loop within Molly Stark State Park, leading to Mount Olga.
The duration of easy hikes in Windham County varies depending on the trail length and your pace. Many easy routes, such as the Haystack Mountain Trail (2.1 miles), can be completed in about 1 hour. Longer easy loops like the Pinnacle at Windmill Hill Loop (3.5 miles) might take around 1 hour 40 minutes to 2 hours.
While many trailheads in Windham County are best accessed by car, some areas, particularly around larger towns, may have limited public transport options. It's recommended to check local bus schedules or ride-sharing services for specific trailheads, as direct public transport to all remote easy trails is not widely available.
Most easy hiking trails in Windham County have designated parking areas at their trailheads, especially those located within state parks or popular recreational zones. For specific routes, it's always best to check the tour details on komoot for information on parking availability and directions to the trailhead.


Check out more Hikes throughout Windham County below and find the perfect route in your destination.
Browse the best Hikes in other regions.