52
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13
hikes
Hiking around Gaylordsville, a village in New Milford, Connecticut, offers diverse landscapes shaped by the Housatonic River and surrounding mountainous terrain. The region features river valleys, woodlands, and elevated areas like Straits Mountain and Long Mountain. These natural features contribute to varied hiking experiences, from riverside paths to trails with elevation changes.
Last updated: May 31, 2026
2
hikers
2.51km
00:56
240m
10m
Embark on an easy hike along the Schaghticoke Mountain via Appalachian Trail, a 1.6-mile (2.5 km) route that takes about 55 minutes to complete. You will gain 803 feet (245…
1
hikers
3.63km
01:12
220m
40m
Hike an easy 2.3-mile section of the Appalachian Trail from Bull's Bridge to Ten Mile Hill, featuring river views and a historic covered bri

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2.67km
00:50
140m
30m
Hike an easy 1.7-mile section of the Appalachian Trail from Hoyt Road to Leather Hill Road, featuring river views and Ten Mile Hill.
9.98km
02:34
50m
50m
Hike the moderate 6.2-mile Housatonic River Trail, enjoying river views and diverse wildlife over 162 feet of elevation gain.
2.59km
00:53
190m
10m
Hike the easy 1.6-mile Housatonic Range Trail for western views of the Housatonic River valley and Candlewood Mountain.
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This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.
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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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A narrow steel bridge spans the Tenmile River just before it joins the much wider Housatonic River. Right next to it is a campsite with easy access.
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Gaylordsville offers a selection of around 14 hiking trails, catering to various preferences and skill levels. These include easy riverside walks and more challenging ascents into the mountainous terrain.
Yes, Gaylordsville features 8 easy hiking routes, perfect for beginners or families. An excellent choice is the Schaghticoke Mountain via Appalachian Trail, which is 1.6 miles long and offers a gentle introduction to the area's natural beauty.
The terrain around Gaylordsville is diverse, shaped by the Housatonic River and surrounding mountains. You'll find river valleys, dense woodlands, and elevated areas like Straits Mountain and Long Mountain. Trails range from flat, gravel paths along the river to more rugged, ascending routes.
Yes, for those seeking a more strenuous experience, Gaylordsville offers 2 difficult routes. These trails typically feature greater elevation changes and more rugged paths, providing a rewarding challenge for experienced hikers.
Hikers can explore several natural features and landmarks. The Housatonic River is a prominent feature, with trails often running alongside it. You can also visit the historic Bulls Bridge, a picturesque covered wooden bridge. The River Trail itself offers scenic viewpoints, and the Ten Mile River Bridge & campsite is another interesting spot near the river's junction.
Many trails in Gaylordsville are dog-friendly, allowing you to enjoy the outdoors with your canine companion. The Housatonic River Trail is a great option for a longer walk with your dog, offering pleasant riverside scenery.
While specific loop trails are not detailed in every guide, many routes in the region can be combined or are part of larger networks that allow for circular exploration. The area's diverse terrain often provides opportunities to create your own loop by connecting different segments.
Gaylordsville offers beautiful hiking opportunities throughout the year. Spring brings lush greenery, while autumn is particularly stunning with vibrant fall foliage, especially around areas like Lake Waramaug State Park. Summer is ideal for riverside walks, and winter can offer peaceful, snow-covered landscapes.
Public transport options directly to specific trailheads in Gaylordsville are limited. It is generally recommended to use a personal vehicle to access most hiking routes in the area, as this provides the most flexibility for reaching starting points.
Parking is typically available at or near the trailheads for most routes. For example, the New Milford River Trail has designated parking areas. It's advisable to check specific route details for the most convenient parking locations before you head out.
Hikers often praise Gaylordsville for its diverse landscapes, from the tranquil Housatonic River to the varied woodlands and mountainous terrain. The presence of sections of the Appalachian Trail and historic sites like Bulls Bridge also adds to the appeal, offering a mix of natural beauty and cultural interest.
Yes, after your hike, you can explore nearby attractions. Lake Waramaug State Park is a short drive away, offering picnic areas and scenic views, especially beautiful in autumn. The historic Bulls Bridge is also a popular spot for a break.


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