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Lower Connecticut River Valley Planning Region

Middletown

The best family-friendly hikes and walks around Middletown

4.5

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Family friendly hiking trails around Middletown traverse a landscape characterized by rolling hills, dense woodlands, and significant geological features. The region offers a comprehensive network of trails, often leading to scenic vistas, waterfalls, and historical sites. Hikers can explore areas featuring century-old white pine stands, reservoirs, and varied terrain from easy strolls to moderate climbs.

Best family friendly hiking trails around Middletown

  • The most popular family friendly hiking route is Main Trail, a 3.7 miles (5.9 km) trail that…

Last updated: July 7, 2026

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#1.

Mattabesett Trail: River Road to Bear Hill Road

9.87km

02:46

240m

130m

The Mattabesett Trail: River Road to Bear Hill Road offers a genuinely rugged and scenic hiking experience through Middletown, Connecticut. This moderate 6.1-mile (9.9 km) hike, with its 788 feet…

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Moderate

4.5

(4)

22

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5.89km

01:35

70m

70m

The Main Trail offers a delightful, easy hiking experience, perfect for a relaxing stroll through nature. You'll encounter the serene Wadsworth Little Falls and the more impressive Wadsworth Falls, providing…

Easy
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5.0

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Embark on the Mattabesett and Reservoir Loop Trail, a moderate 7.9-mile (12.8 km) hike that takes about 3 hours and 31 minutes to complete. You will gain 735 feet (224…

Moderate

1

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3.14km

00:50

30m

30m

The Reservoir Loop Trail provides an easy hike through natural landscapes, circling Asylum Reservoir No. 2. You can expect a pleasant walk with views of the water and sections winding…

Easy

The Giant Laurel – Wadsworth Little Falls loop is a charming and accessible hiking trail that winds through the mixed woodlands of Wadsworth Falls State Park. This easy 2.2-mile (3.5…

Easy
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Tips from the Community

Lisa
September 28, 2024, Coginchaug River Dam (Pistol Shop Dam)

This dam is a relic of the era's industrialized past, when both the Coginchaug and Sumner-Pameacha stream systems had more than a dozen power-producing dams each.

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I'd love to visit, hike the trails, find the best viewpoints, and maybe even dig a little deeper into the background of how these reservoirs came to be. https://geometrydashmeltdown.io

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Lisa
February 25, 2024, Wadsworth Falls

It's well worth hopping off your bike here for the short walk to Wadsworth Falls, AKA Wadsworth Big Falls. This is widely considered one of the best waterfalls in Connecticut, and its 30-foot drop is especially impressive after a big rain.

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This waterfall is considered one of the best in the entire state. It offers a perfect place to cool off and enjoy the sights and sounds. It is best to visit after rainfall, as the waterfall becomes more impressive. However, be cautious and watch your footing, as the rocks can get slick. Make sure you step off the bike before heading down the path.

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A section of the Mattabesett Trail passes through Cockaponset State Forest and provides access to some of the other hiking trails around the reservoirs. This is a really popular trail that's marked well with different color blazes. There are signs at the trailheads letting you know which blazes to follow for which trails.

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This is an overlook area for Asylum Reservoir #2 (the most popular and largest of the 3 reservoirs). The reservoirs were originally constructed to supply water to the mental hospital nearby, which is why they are named the way they are. There are a bunch of different spots to view the lake, and the trails on the property are marked really well.

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This waterfall is considered one of the best in the entire state. It offers a perfect place to cool off and enjoy the sights and sounds. It is best to visit after rainfall, as the waterfall becomes more impressive. However, be cautious and watch your footing, as the rocks can get slick.

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They rightly named it Wadsworth Little Falls because it is a smaller version of its older sibling, Wadsworth Falls, but nonetheless, it remains an impressive site.

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Frequently Asked Questions

How many family-friendly hiking trails are available in Middletown?

Our guide features 6 family-friendly hiking trails around Middletown, ranging from easy strolls to more moderate adventures. These routes are carefully selected to ensure an enjoyable experience for all ages.

Are there easy hiking options suitable for young children or strollers?

Yes, Middletown offers several easy trails perfect for families with young children or those using strollers. The Main Trail in Wadsworth Falls State Park is an excellent choice, offering a relatively flat path through beautiful scenery. Another great option is the Giant Laurel – Wadsworth Little Falls loop, also within Wadsworth Falls State Park, which is easy and features scenic waterfalls.

Can we find trails with waterfalls in Middletown?

Absolutely! Wadsworth Falls State Park is a prime location for waterfall hikes. You can explore the accessible Wadsworth Falls and Wadsworth Little Falls. The Giant Laurel – Wadsworth Little Falls loop is an easy route that takes you right past these beautiful natural features.

Are there any loop trails suitable for families?

Yes, loop trails are great for families as they bring you back to your starting point. The Mattabesett and Reservoir Loop Trail offers a moderate, longer option, while the shorter Reservoir Loop Trail is an easy choice, providing scenic views of the forested watershed.

What kind of scenic views can we expect on family hikes in Middletown?

Middletown's trails offer diverse scenic views. You can enjoy panoramic vistas from higher elevations like Mount Higby, explore dense woodlands, and discover significant geological features. Trails around the Middletown Reservoirs provide stunning views of Monhagen, Highland, and Shawangunk Reservoirs, often featuring century-old white pine stands. Many routes also offer glimpses of the Connecticut River.

Are there any interesting landmarks or attractions along the trails?

Yes, several trails lead to or pass by interesting landmarks. In Wadsworth Falls State Park, you'll find a historic covered bridge and a beautiful stone bridge. The Mattabesett and Reservoir Loop Trail offers views of the Bradley Hubbard Reservoir. For broader views, consider visiting Castle Craig, a unique stone tower offering expansive vistas, or the Crescent Lake Park area.

What do other hikers enjoy most about family-friendly trails in Middletown?

The komoot community highly rates the family-friendly trails in Middletown, with an average score of 4.5 stars. Hikers often praise the well-maintained paths, the natural beauty of areas like Wadsworth Falls State Park, and the variety of trails suitable for different ages and abilities. The accessibility of scenic spots and the peaceful atmosphere are frequently highlighted.

Are dogs allowed on the family-friendly hiking trails?

Many trails in Middletown's state parks and preserves are dog-friendly, typically requiring dogs to be on a leash. It's always a good idea to check specific park regulations before you go, but generally, you'll find plenty of options to enjoy with your leashed canine companion.

What is the best season for family hiking in Middletown?

Middletown offers enjoyable hiking experiences year-round. Spring brings lush greenery and blooming wildflowers, while summer provides warm weather for exploring. Autumn is particularly stunning with vibrant fall foliage, making it a popular time for scenic walks. Even in winter, many trails are accessible for a crisp, quiet hike, especially after a light snowfall.

Is parking available at the trailheads?

Yes, most popular trailheads and parks in Middletown, such as Wadsworth Falls State Park and the Middletown Reservoir areas, offer designated parking facilities. It's generally easy to find parking, especially for family-friendly routes.

Are there any trails accessible by public transport?

While many trailheads are best reached by car, some areas within Middletown are served by local bus routes. For specific public transport options to trailheads, it's recommended to check the Middletown Area Transit (MAT) schedules and routes, as direct access can vary.

Where can we find longer, moderate family hikes?

For families looking for a bit more of a challenge, the Mattabesett Trail: River Road to Bear Hill Road offers a moderate 9.8 km route with some elevation gain, providing a rewarding experience. Another moderate option is the Mattabesett and Reservoir Loop Trail, which is longer at 12.7 km and features varied terrain.

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