The best walks and hikes around Windsor
4.5
(7)
128
hikers
13
hikes
Hiking around Windsor is characterized by the forested slopes of Mount Ascutney, which provides a range of trail options. The region offers a mix of challenging ascents to the mountain's summit and more gentle routes around local parks. The trail network primarily consists of paths through dense woodland, with significant elevation changes on the routes leading up the mountain.
Best hiking trails around Windsor
- The most popular hiking route is Mount Ascutney via Windsor Trail — Mount Ascutney State Park…
Last updated: May 12, 2026
1
hikers
4.46km
01:11
50m
50m
The Paradise Park Loop invites you to an easy hike around the serene Lake Runnemede, where you can enjoy a tranquil journey through natural beauty and lush greenery. This route…
5.0
(1)
19
hikers
8.62km
03:29
680m
680m
Hike the moderate Brownsville Trail in Mount Ascutney State Park, a 5.4-mile route with scenic views and forested paths.
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18
hikers
8.10km
03:25
710m
710m
Hike the challenging Windsor Trail up Mount Ascutney, featuring Gerry's Falls and panoramic views from the summit observation tower.
3.0
(1)
9
hikers
13.7km
04:56
820m
820m
Hike the moderate 8.5-mile Futures Trail in Mount Ascutney State Park, gaining 2696 feet with panoramic views from the summit.
5.0
(1)
4
hikers
5.96km
01:34
50m
50m
Embark on the easy Ridge and Lakeside Loop, a pleasant hike that takes you through diverse forest environments and along the shoreline of Lake Runnemede. You will enjoy continuous glimpses…
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Tips from the Community
Lake Runnemede is a great place for a break during a long ride. The large body of water is home to many species of birds and fish. The water is visible from the road, so if you don't have time to stop, you can still get a great view as you ride by.
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This is a lovely run around the shores of Lake Runnemede along a relatively flat and grassy footpath that's right up on the water's edge, creating lovely scenes as you make your way around.
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From Brownsville Rock, you are afforded superb views north towards the Green Mountains. The viewpoint features a protruding rock which makes a great place to sit and enjoy some lunch.
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Gerry's Falls is one of five seasonal waterfalls dotted around the slopes of Mount Ascutney. The water flows down exposed bedrock and boulders between ferns, and then cascades into a waterslide.
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The shoreline of Lake Runnemede is a nice area for a walk. You can see Mount Ascutney in the background.
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Trails from all directions lead to the summit of Mount Ascutney. There's a lookout tower that takes you above the trees for great views.
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Frequently Asked Questions
Are there any easy, family-friendly walks in the Windsor area?
Yes, for a gentler experience away from the mountain ascents, the Lake Runnemede Loop – Paradise Park Windsor is an excellent choice. It's a relatively flat, 3.7-mile (6.0 km) trail that's perfect for families and those looking for a relaxed walk.
What are the hiking options on Mount Ascutney?
Mount Ascutney offers several trails to the summit, primarily through dense woodland. You can choose from routes like the Mount Ascutney via Weathersfield Trail, which provides a steady climb. Most routes involve significant elevation gain, making for a rewarding challenge.
How difficult are the hikes around Windsor?
The trails offer a good mix of difficulties. There are about a dozen marked trails, split almost evenly between easy and moderate. The majority of routes involve challenging ascents up Mount Ascutney, while easier options can be found in local parks at lower elevations.
Are the trails around Windsor suitable for a full-day hike?
Yes, if you're looking for a longer adventure, consider the Mount Ascutney via Future's Trail. At over 8.5 miles (13.7 km) and with considerable elevation, it's a strenuous route that can take over 4.5 hours, making it ideal for a challenging day out.
What is the terrain like on the trails?
The hiking is primarily characterized by the forested slopes of Mount Ascutney. Expect paths that wind through dense woodland with significant elevation changes on the mountain trails. The ground is often uneven with roots and rocks. Lower elevation park trails are generally flatter and easier underfoot.
Are there any circular or loop trails available?
Yes, there are loop trails available. The Lake Runnemede Loop in Paradise Park is a popular circular route for an easier walk. Many of the trails on Mount Ascutney are out-and-back ascents, but they can often be combined with other paths to form a loop.
What do other hikers think of the trails near Windsor?
The trails in this region are highly rated by the komoot community, with an average score of 4.7 out of 5 stars. Hikers often praise the challenging but rewarding climbs on Mount Ascutney and the beautiful forest scenery.
How long do most moderate hikes in the area take?
A typical moderate hike, like the Mount Ascutney via Windsor Trail, is about 5 miles (8.1 km) and takes around 3.5 hours to complete, involving a steep climb to the summit.
Can I hike in Mount Ascutney State Park?
Absolutely. Mount Ascutney State Park is the main hub for hiking in the area, containing most of the popular trails. Routes like the Mount Ascutney via Brownsville Trail start and finish within the park, offering well-maintained paths through the forest to the summit.
Are there good views on the hikes near Windsor?
Yes, the summit of Mount Ascutney provides excellent panoramic views of the surrounding landscape. The effort of the climb is rewarded with far-reaching vistas, making it a highlight for many hikers in the region.
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