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Routes
Running Trails
United States
Vermont
Windsor County

Windsor

The best running trails around Windsor

59

runners

6

runs

Jogging routes around Windsor offer a variety of experiences across its diverse terrain. The region is characterized by rolling hills, dense woodlands, and scenic river valleys, providing varied landscapes for runners. Trails often feature significant elevation changes, leading through forested areas and past natural water features. This environment supports a range of running experiences, from moderate loops around lakes to more challenging routes with substantial climbs.

Best jogging routes around Windsor

  • The most popular jogging route is Weathersfield Trail,…

Last updated: May 10, 2026

9

runners

#1.

Weathersfield Trail

7.14km

01:15

530m

530m

Jog the difficult 4.4-mile Weathersfield Trail in Mt. Ascutney State Park, gaining 1732 feet to panoramic views from the summit.

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Hard

Enjoy a moderate 3.1-mile (5.0 km) jogging loop around Lake Runnemede in Windsor's Paradise Park, featuring forests, fields, and lake views.

Moderate
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Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

6

runners

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

4

runners

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Popular around Windsor

Hiking around Windsor

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Cycling around Windsor

Gravel biking around Windsor

Tips from the Community

mtm05005
February 26, 2024, Lake Runnemede

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.

1

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Grace Mulligan
December 22, 2023, Lake Runnemede

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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Whilst this is not quite the peak of Mount Ascutney, the views west from here are superb. You'll be able to see over Vermont including Killington, Pico, and Okemo. This is also a great spot to see gliders being launched, hence the name of the trail up to the viewpoint being called 'Hang Glider Trail'.

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This is a challenging but rewarding trail leading to Mount Ascutney. It's steep and rocky but incredibly scenic at the same time. When you reach the top, you'll be rewarded with sublime views west over Vermont toward Killington, Pico, and Okemo.

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Grace Mulligan
December 4, 2023, Gerry's Falls

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.

1

0

Mareike
December 20, 2022, Lake Runnemede

The shoreline of Lake Runnemede is a nice area for a walk. You can see Mount Ascutney in the background.

0

0

This view is at the top of a brutal gravel climb. I’m not messing around - it’s steep and loose, but you will be rewarded with this amazing view which reminds me of the Swiss Alpine lowlands.

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Frequently Asked Questions

How many running routes are available in Windsor?

The komoot guide features 7 curated running routes around Windsor, offering a variety of experiences across its diverse terrain. These routes range from moderate loops to more challenging trails with significant elevation changes.

Are there any easy or beginner-friendly running routes in Windsor?

While most routes in the guide are challenging, the Lake Runnemede 5k running loop from Windsor is a moderate option. This path offers a scenic loop around the lake with minimal elevation changes, making it suitable for those looking for a less strenuous run. Additionally, in Windsor, UK, the Thames Path or the Long Walk in Windsor Great Park offer generally flat and accessible options.

Where can I find challenging running trails around Windsor?

For experienced runners seeking a challenge, Windsor offers several difficult routes with considerable elevation gain. The Weathersfield Trail is a difficult 4.4-mile route with significant elevation through wooded terrain. Another demanding option is the Bowers Covered Bridge loop from West Windsor, a 15.3-mile trail leading through varied landscapes.

What kind of landscapes can I expect on running trails in Windsor?

Running routes around Windsor are characterized by diverse landscapes. You'll find forested hills, scenic river valleys, and tranquil lakes. Depending on the Windsor location, this can include the expansive green spaces of Windsor Great Park in the UK, the urban waterfronts and natural preserves of Windsor, Ontario, or the community-focused trails and parks of Windsor, Colorado.

Are there any scenic running routes that offer views or natural beauty?

Yes, many routes in Windsor are highly scenic. The Lake Runnemede 5k running loop provides beautiful lakeside views. In Windsor, UK, the Thames Path and routes within Windsor Great Park, including Virginia Water, offer stunning natural beauty. Windsor, Ontario boasts the Detroit Riverfront Trail with city skyline views, and Windsor, Colorado has the Poudre River Trail known for diverse scenery and wildlife.

Are there any routes that pass by waterfalls or other natural attractions?

Yes, the Gerry's Falls loop from West Windsor is a difficult 9.7-mile route that passes by natural features, including waterfalls. You can also find Little Cascade Falls as a highlight in the area. Additionally, the Lake Runnemede is a prominent natural attraction featured in one of the running loops.

What are some good options for circular running routes in Windsor?

Several routes in the area are designed as loops, perfect for circular runs. The Lake Runnemede 5k running loop is a popular moderate option. For a longer, more challenging circular route, consider the Bowers Covered Bridge loop from West Windsor.

Are there dog-friendly running trails in the Windsor area?

While specific dog-friendly designations vary by location and park rules, many natural areas in Windsor are generally welcoming to dogs on leash. For instance, Windsor Great Park in the UK and Malden Park in Windsor, Ontario, are popular spots for runners with dogs. Always check local regulations for specific trails before heading out with your canine companion.

What are the best running routes for winter in Windsor?

For winter running, conditions can vary greatly depending on the Windsor location. In Windsor, Ontario, the Herb Gray Parkway Trail is often lit and plowed, making it suitable for winter use. Malden Park and Ojibway Preserve/Woods also offer wooded environments that can provide some protection from snow. Always exercise caution and check local conditions during winter months.

Are there any historical or cultural landmarks I can see while running in Windsor?

Yes, depending on the Windsor location, you can encounter various landmarks. In Windsor, UK, routes often feature views of Windsor Castle and the historic Eton College. The Bowers Covered Bridge loop from West Windsor passes by a historic covered bridge. In Windsor, Ontario, the waterfront features the Windsor Sculpture Park.

What do other runners enjoy most about the trails in Windsor?

Runners frequently praise the diverse terrain and natural beauty of Windsor's trails. The komoot community highlights the significant elevation changes on many routes, providing a good workout, as well as the tranquil lakes and forested areas that offer a peaceful running experience. The variety of options, from moderate lakeside loops to challenging climbs, is also a popular aspect.

Are there any longer running routes for experienced runners?

Absolutely. For those looking for longer distances, the Bowers Covered Bridge loop from West Windsor is a substantial 15.3-mile (24.6 km) trail, often completed in about 3 hours. This route offers varied landscapes and significant elevation, making it ideal for experienced runners seeking endurance challenges.

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