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United States
Connecticut
Northwest Hills Planning Region

Gaylordsville

Easy hikes and walks around Gaylordsville

52

hikers

13

hikes

Easy hiking trails around Gaylordsville, a village in New Milford, Connecticut, offer diverse natural landscapes and extensive trail networks. The region is characterized by the Housatonic River, which flows through its center, providing a picturesque backdrop for many activities. Varied woodlands, including areas with red cedars and towering tulip poplars, contribute to the scenic beauty. Straits Mountain and "the Pinnacle" provide varied elevations and potential viewpoints, making the area suitable for exploring on foot.

Best easy hiking trails around Gaylordsville

Last updated: June 1, 2026

2

hikers

#1.

Schaghticoke Mountain via Appalachian Trail

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…

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Easy

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

Easy
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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.

Easy

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.

Easy

2.20km

00:41

100m

50m

Enjoy an easy 1.4-mile hike on the Bull Mountain Trail Loop in Bull Mountain Preserve, featuring 337 feet of elevation gain.

Easy
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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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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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Frequently Asked Questions

How many easy hiking trails are there around Gaylordsville?

Gaylordsville offers a good selection of easy hiking trails, with over 10 routes specifically categorized as easy. These trails are perfect for those looking for a gentle walk or a family-friendly outing.

What makes the easy hiking trails in Gaylordsville suitable for beginners or families?

The easy trails in Gaylordsville are generally characterized by gentle gradients and well-maintained paths, making them ideal for beginners, children, and families. Many routes, like the sections of the Appalachian Trail, offer relatively flat terrain through scenic woodlands and along the Housatonic River, ensuring an enjoyable experience for all skill levels.

Are there any easy loop hikes in Gaylordsville?

Yes, there are easy loop options available. For example, the Bull Mountain Trail Loop provides a manageable circular route, allowing you to experience varied scenery without retracing your steps.

What kind of scenery can I expect on easy hikes around Gaylordsville?

You can expect diverse and picturesque scenery. Many easy trails follow the scenic Housatonic River, offering tranquil river views. You'll also encounter varied woodlands, including red cedars and towering tulip poplars, and open meadows. Some areas, like the Strauss Morrissey Preserve, feature unique flora supported by marble bedrock, adding to the natural beauty.

Are there any historical landmarks or points of interest along the easy trails?

Absolutely! A significant landmark is Bulls Bridge, a historic covered wooden bridge spanning the Housatonic River, which you can encounter on routes like the Appalachian Trail: Bull's Bridge to Ten Mile Hill. The region also has historical sites like the Little Red Schoolhouse and Brown's Forge, offering a blend of history and nature.

Can I bring my dog on the easy hiking trails in Gaylordsville?

Many trails in the Gaylordsville area are dog-friendly, but it's always best to check specific trail regulations before you go. Generally, trails that pass through state parks or preserves welcome leashed dogs. The Housatonic River trails are often popular choices for walks with canine companions.

What is the best time of year to enjoy easy hikes in Gaylordsville?

Gaylordsville's easy hikes are enjoyable year-round. Spring brings lush greenery and blooming wildflowers, while summer offers warm weather for riverside strolls. Autumn is particularly stunning, with vibrant fall foliage along the Housatonic River and in the surrounding woodlands. Even winter can be beautiful for a crisp walk, though some paths might be icy or snowy.

Are there easy trails that offer views of the Housatonic River?

Yes, the Housatonic River is a defining feature of the region, and many easy trails run alongside it. The River Trail, for instance, offers consistent river views and is a pleasant, flat route through quiet woods. Sections of the Appalachian Trail in the area also follow the river.

Where can I find parking for easy hikes in Gaylordsville?

Parking is generally available at trailheads and designated access points for many of the easy hikes. For trails like those along the Appalachian Trail or near Bulls Bridge, you'll typically find small parking areas. It's advisable to check specific route details on komoot for precise parking information before your trip.

Is public transport available to access hiking trails in Gaylordsville?

Public transport options directly to trailheads in Gaylordsville can be limited. The area is more accessible by car. However, some regional bus services might connect to nearby towns, from which you could potentially arrange local transport or a short taxi ride to reach certain trail access points.

What do other hikers say about the easy trails in Gaylordsville?

The easy trails in Gaylordsville are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the tranquil atmosphere, the beautiful river views, and the well-maintained paths that make for a relaxing and accessible outdoor experience.

Are there any easy trails that pass by Lake Waramaug State Park?

While not directly adjacent to all easy trails in Gaylordsville, Lake Waramaug State Park is a significant nearby attraction offering its own network of trails and recreational opportunities. You can find easy walks within the park itself, making it a great destination to combine with your Gaylordsville hiking plans.

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