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Routes
Hiking trails & Routes
United States
Connecticut
Lower Connecticut River Valley Planning Region
Middletown

Bear Hill Loop

Moderate

3.1

(5)

33

hikers

Bear Hill Loop

04:50

17.3km

290m

Hiking

Embark on the Bear Hill Loop, a moderate hiking route spanning 10.7 miles (17.3 km) with an elevation gain of 944 feet (288 metres), typically taking around 4 hours and 50 minutes to complete. You will navigate rocky ups and downs, encountering bedrock blazes and open face rock sections, especially…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

4.51 km

Intermittent Waterfall

Waterfall

2

7.38 km

Bear Hill

Highlight • Viewpoint

This small hill sits along the Mattabesett Trail at only 652 ft high, with a rock overcrop that offers a splendid view above the Spiderweed Preserve. This can be a nice place to watch the sunset and have a picnic.

Tip by

10.6 km

Viewpoint

Viewpoint

11.9 km

Viewpoint

Viewpoint

B

17.3 km

End point

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Way Types & Surfaces

Way Types

9.09 km

8.12 km

< 100 m

Surfaces

9.13 km

8.07 km

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (190 m)

Lowest point (30 m)

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Weather

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Today

Friday 8 May

16°C

3°C

20 %

Additional weather tips

Max wind speed: 20.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the overall difficulty and terrain like on this trail?

This route is rated as moderate, featuring rocky ups and downs. Hikers should be prepared for varied terrain, including bedrock blazes and open face rock sections. Some parts, particularly the yellow-blue blazed section, can be muddy and show signs of ATV use.

How long does it typically take to complete the Bear Hill Loop?

The full Bear Hill Loop, as mapped, typically takes around 4 hours and 50 minutes to complete. This duration can vary based on your pace and how often you stop to enjoy the scenery.

What are the best times of year to hike this trail?

June is an excellent time to visit to see blooming mountain laurel, and blueberries may be ripening in late June and July. For expansive views over the trees, consider hiking when there is less foliage, such as late fall or early spring. Winter hiking is possible, but be aware that some sections can be snow-packed and icy, making spikes advisable.

Are there any notable viewpoints or landmarks along the way?

Yes, the route includes the Bear Hill highlight, which offers views over the trees. These views are often more prominent when the foliage is not dense.

Does this trail connect with other hiking paths?

Yes, this route is largely part of the longer Mattabesett Trail and the New England National Scenic Trail. It also incorporates sections of the Bear Hill Trail and the Reservoir Loop Trail.

Is the Bear Hill Loop dog-friendly?

Generally, dogs are permitted on trails within Connecticut's state forests and wildlife management areas, including the Maromas Wildlife Management Area where this trail is located. It is always recommended to keep dogs on a leash and practice Leave No Trace principles.

What should I know about parking and trailhead access?

While specific parking details for this exact loop are not provided, as part of the Mattabesett Trail within the Maromas Wildlife Management Area, access points typically involve parking areas near trailheads. It's advisable to check local regulations or maps for designated parking locations before your visit.

Are there any permits or fees required to access the Maromas Wildlife Management Area?

As of current information, there are typically no entrance fees or permits required for general hiking access to the Maromas Wildlife Management Area in Connecticut. However, always check the official Connecticut Department of Energy and Environmental Protection (DEEP) website for the most up-to-date regulations before your visit.

What should I pack for a hike on this trail?

Given the moderate difficulty and varied terrain, sturdy hiking boots are recommended. In winter, consider bringing spikes for icy sections. Always carry enough water, snacks, a map or GPS device, and appropriate layers for changing weather conditions. Bug spray can also be useful, especially during warmer months.

Are there any amenities like cafes or restaurants near the trailhead?

The Bear Hill Loop is located within the Maromas Wildlife Management Area, which is a natural, undeveloped area. Therefore, amenities like cafes or restaurants are not directly at the trailhead. You would need to travel to nearby towns, such as Middletown, for dining options.

Is this trail suitable for beginners or families with young children?

Given its moderate difficulty, rocky terrain, and nearly 5-hour duration, this specific Bear Hill Loop might be challenging for absolute beginners or very young children. Hikers should have a reasonable level of fitness and experience with varied trail conditions.

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