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Hiking trails & Routes
Lower Connecticut River Valley Planning Region
Middletown

Bear Hill Loop Trail

Easy

Bear Hill Loop Trail

01:02

3.71km

100m

Hiking

Embark on the Bear Hill Loop Trail, an easy hiking route that winds for 2.3 miles (3.7 km) through varied terrain. You will encounter rocky ups and downs, including sections of bedrock and open face rock, as you gain 327 feet (100 metres) in elevation. The trail offers a rewarding…

Last updated: April 23, 2026

Waypoints

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Start point

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1

2.51 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.

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3.71 km

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Way Types & Surfaces

Way Types

3.61 km

< 100 m

Surfaces

3.60 km

110 m

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Elevation

Elevation

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Weather

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Today

Friday 3 July

36°C

24°C

38 %

Additional weather tips

Max wind speed: 17.0 km/h

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Frequently Asked Questions

How difficult is the Bear Hill Loop Trail?

The Bear Hill Loop Trail in Connecticut is generally considered to be of moderate difficulty. While komoot rates it as 'easy' overall, sections can be challenging due to rocky ups and downs, bedrock, and open face rock. It's a varied experience that requires attention to the ground.

What is the terrain like on the trail?

The terrain is quite diverse. You'll encounter rocky sections, including bedrock with blazes, and open face rock as you gain elevation. Parts of the route pass through dense woodlands, and you may cross a utility corridor or streams. Some areas can be muddy, especially after rain.

What kind of views can I expect on the route?

The trail offers picturesque views, particularly when foliage is less dense. A notable wide-open view facing north can be found where the blue and yellow-blue trails diverge, featuring twisted pitch pine trees. You can also catch glimpses of the Connecticut River and surrounding hills. The route also passes by the Bear Hill viewpoint.

What is the best time of year to hike this trail?

June is an excellent time to visit, as the mountain laurel is in full bloom, creating beautiful scenery. Late June and July offer the chance to spot ripening blueberries along the trail. Views are often more expansive when trees are bare, making late fall to early spring also appealing for vistas.

Is the Bear Hill Loop Trail dog-friendly?

Yes, dogs are generally welcome on the Bear Hill Loop Trail. However, it's always recommended to keep your dog on a leash to protect wildlife and ensure a pleasant experience for all hikers, especially given the varied terrain and potential for encountering other trail users.

Where can I park for the Bear Hill Loop Trail?

The main trailhead for this route is accessible from Bear Hill Road in Middletown, CT. Parking is available there, making it convenient to start your hike.

Are there any permits or fees required for hiking in Maromas Wildlife Management Area?

No, there are typically no specific permits or entrance fees required for hiking the Bear Hill Loop Trail within the Maromas Wildlife Management Area. However, always check the official Connecticut Department of Energy and Environmental Protection (DEEP) website for any updated regulations or advisories before your visit.

Does the trail intersect other well-known paths?

Yes, the Bear Hill Loop Trail is interconnected with a larger trail system. It zigs and zags across sections of the longer Mattabesett Trail and also follows parts of the New England National Scenic Trail, allowing for various loop options and extended hikes.

What makes this trail particularly notable or unique?

This trail is notable for its stunning mountain laurel blooms in June, its interconnectedness with the Mattabesett Trail allowing for customizable loop lengths, and its diverse ecosystem ranging from dense woodlands to rocky sections. It also offers a specific wide-open northern view that is a local highlight.

What should I wear or bring for this hike?

Given the rocky and potentially muddy terrain, sturdy hiking boots are highly recommended. Layers are always a good idea, and bringing water is essential. If hiking in late spring or summer, insect repellent can be useful, and binoculars might enhance your enjoyment of the views and wildlife.

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