3.1
(5)
33
hikers
04:50
17.3km
290m
Hiking
The Bear Hill Loop in Middletown, Connecticut, offers a dynamic hiking experience through dense woodlands, characterized by a mix of rocky ascents and descents, open face rock sections, and occasional muddy stretches. You'll traverse varied terrain, with the reward of seasonal highlights like blooming mountain laurel in June and ripening…
Last updated: June 9, 2026
Waypoints
Start point
Parking
Get Directions
4.51 km
Intermittent Waterfall
Waterfall
7.38 km
Highlight • Viewpoint
Tip by
10.6 km
Viewpoint
Viewpoint
11.9 km
Viewpoint
Viewpoint
17.3 km
End point
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
Highest point (190 m)
Lowest point (30 m)
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Weather
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Sunday 23 August
28°C
19°C
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This route was planned by komoot.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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