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Routes
Running Trails
United States
Connecticut
Northwest Hills Planning Region

Gaylordsville

The best running trails around Gaylordsville

33

runners

9

runs

Jogging around Gaylordsville, a village in New Milford, Connecticut, provides access to diverse landscapes. The area features the Housatonic River, which forms a central natural feature, along with varied terrain that includes woodlands and hills. Running routes often incorporate elevation changes, traversing from riverfront paths to wooded areas and features like "the Pinnacle." This region offers a range of running trails suitable for different fitness levels.

Best jogging routes around Gaylordsville

  • The most popular jogging route is River Trail loop…

Last updated: June 8, 2026

6

runners

#1.

Zalesskys Pond – Parkhurst Pond loop from New Milford

12.8km

01:22

190m

190m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

3

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

3

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Tips from the Community

Caro "Bandit"
February 24, 2022, Bulls Bridge

This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.

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Frequently Asked Questions

How many running routes are available in Gaylordsville?

There are 9 dedicated running routes around Gaylordsville, offering a variety of experiences for different fitness levels. These include 7 moderate routes and 2 more challenging options.

Are there any easy or beginner-friendly jogging routes in Gaylordsville?

While there are no routes explicitly rated 'easy', many of the 7 moderate routes are suitable for those looking for a manageable run. For example, the Spring Lake loop from Town Meadows is a moderate 5-mile route with a relatively gentle elevation gain, making it a good option for beginners.

What kind of terrain can I expect on Gaylordsville's running trails?

Gaylordsville's running trails offer diverse terrain, from riverfront paths along the Housatonic River to wooded areas and routes with elevation changes. You'll find a mix of surfaces, including some paved sections and more natural trails, providing varied experiences for runners.

Are there any scenic loop routes for running in Gaylordsville?

Yes, Gaylordsville features several scenic loop routes. A popular choice is the River Trail loop from Gaylordsville, an 8.9-mile route offering excellent views of the Housatonic River. Another option is the Bulls Bridge loop from Bull's Bridge, which leads through beautiful riverine landscapes.

What natural attractions or landmarks can I see while jogging in Gaylordsville?

Many running routes in Gaylordsville offer views of the Housatonic River, especially beautiful in autumn. You can also explore areas like the Strauss Morrissey Preserve with its varied woodlands. Nearby attractions include Bulls Bridge and the River Trail itself. The historic Steep Rock Tunnel is also a unique point of interest in the vicinity.

Are the running trails in Gaylordsville suitable for families?

While specific 'family-friendly' ratings aren't provided, the moderate routes with less significant elevation, such as the Spring Lake loop from Sherman (5.7 miles), could be enjoyable for active families. The varied landscapes and river views offer an engaging outdoor experience for all.

Are there any dog-friendly running trails in Gaylordsville?

Most natural trails in the Gaylordsville area are generally dog-friendly, though it's always recommended to keep your dog on a leash and practice 'leave no trace' principles. The diverse woodlands and river paths provide ample space for you and your canine companion to enjoy a run together.

Where can I find parking for the running routes in Gaylordsville?

Parking availability varies by route. For routes like the River Trail loop from Gaylordsville, you can often find parking near the starting points in the village or designated trailheads. For routes originating from specific locations like 'Bull's Bridge' or 'Town Meadows', look for parking facilities in those areas.

What is the best time of year to go running in Gaylordsville?

The fall is particularly beautiful for running in Gaylordsville, as the leaves along the Housatonic River and in the woodlands display vibrant colors. Spring and summer also offer pleasant conditions, though summer runs might be best enjoyed in the cooler morning or evening hours. Winter running is possible, but trails may be affected by snow or ice.

Are there any running routes that pass by ponds or lakes?

Yes, the Zalesskys Pond – Parkhurst Pond loop from New Milford is an 8-mile moderate route that features varied terrain and passes by local ponds, offering a different scenic element to your run.

What do other runners enjoy most about jogging in Gaylordsville?

Runners often praise the diverse landscapes, from riverfront paths to wooded areas, and the varied terrain that offers options for different ability levels. The scenic views, especially along the Housatonic River, are frequently highlighted as a key draw for the komoot community exploring Gaylordsville.

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