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.
Last updated: June 8, 2026
6
runners
12.8km
01:22
190m
190m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
runners
14.9km
01:33
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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6
runners
13.6km
01:27
200m
200m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
runners
9.15km
00:58
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
runners
8.10km
00:51
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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