Off the Beaten Path: Bear Hill Loop

Bear Hill Loop Trail is a side trail off the Mattabesett Trail. It zig zags across the Mattabesett, creating several options for loops of different lengths. Use the map to create your own route, or follow our favorite option described below. June is a great time to try this hike to enjoy all the blooming mountain laurel. You’ll also experience a variety of terrains, rocky ups and downs, and perhaps even find blueberries ripening in late June and July. There are views over the trees that are even nicer other times of year with less foliage. Another great hike for experiencing mountain laurel is Seven Falls Loop, described here.
To learn more about mountain laurel and other native flowers in bloom, visit the Everyone Outside blog.

Hike Overview
Total length: 4.2 miles with shorter and longer options possible
Difficulty: Moderate
Type: Lollipop loop
Elevation change:  170 feet
Trails: Blue-blazed Mattabesett Trail and yellow-blue Bear Hill Loop Trail
Reference: Connecticut Walk Book, pages 99, 102 and 106-7, Map 20-MB-01

GPS link to trailhead on Bear Hill Road, Middletown, CT

Take exit 11 off Route 9. Turn right onto Route 155/Randolph Rd. In about a quarter mile you’ll hit a traffic light. Turn right onto Saybrook Road and immediately keep left at the fork. In another quarter mile, make a slight left onto Brooks Road. In 0.7 miles turn right onto the unmarked Bear Hill Road. In 0.2 miles the trailhead is on your right.

Spring and summer scenery on the trail:

trail map

The hike begins at the Kätchen Coley Mountain Laurel Preserve sign. There are several dirt pull-off spots nearby to park. Begin following the blue blazes by the sign.

Trailhead Parking

In 0.2 miles you’ll reach a utility corridor that you’ll need to cross. Walking around the blazed pole, turn left to stay on the blue trail. You’ll see stakes in the ground with blue blazes on them ahead.

Reading blazes: When you see two blazes with the top one offset to the left, it indicates the trail makes a left turn. Conversely, if the top blaze is offset to the right, you’d be turning right. Pictured here, the blue trail continues by turning left, and the yellow-blue trail begins by turning right.

You’ll re-enter the woods through a tunnel of mountain laurel. Continue following blue blazes.

You will pass many unmarked trails as you continue. The trails described in this hike are generally well marked, so if you don’t see blazes ahead of you or behind you, turn around and walk back the way you came until you can pick up the blazes again.

Also, there are numerous places where the side of the trail is lined with blueberry and bilberry bushes that ripen by July. As always, don’t eat anything you’re not able to positively identify, though!

When you come to a stream, cross it, walk around the blazed tree and turn right uphill.

You’ll find some blazes painted on the bedrock as you continue. Keeps an eye on both the ground and trees, as well as boulders.

At 1.4 miles into the hike you’ll be crossing a junction with the yellow-blue blazed Bear Hill Loop. We’ll be coming back thru this junction. For now, stay on blue.

As you begin emerging from the dense woodlands and gain elevation, you’ll find increasingly rockier terrain and views through the trees.

After crossing several sections of open face rock, perhaps resting to soak up the sun, you’ll reach another junction with the yellow-blue trail. Here, the two trails merge for a few hundred yards. Turn right and you’ll find yourself on the combined section, with alternating blazes of both blue and yellow-blue.

Continue to ascend a section of rock with a lovely little grove of twisted pitch pine trees at the top. This is where the two trails diverge again (the yellow-blue down hill to the left and the blue down hill to the right). If you look down the line of the yellow-blue trail you’ll find a wide open view facing the north (one of the best views on the hike). For the hike described here,  this will be your turnaround point. To tack on another loop, see Alternative Options at the end of this post.

Turn around and head back down the ledge on the combined trail. Begin looking for yellow-blue blazes and turn right here to start on the yellow-blue trail. This is another good section for finding blueberries.

After a half mile you reach the intersection with the blue trail that you passed earlier in the hike.  Turn right here to retrace your steps through the mountain laurel, utility corridor, and back to your car. Pictured here, you have to step over the deadwood on the right to make the turn. If you miss this turn, or need to shorten your hike, you may continue on the yellow-blue trail back through the utility corridor before rejoining the blue trail again; however, it is not recommended. The yellow-blue trail has unsightly damage from ATV use and some frequently muddy areas.

Alternative Options

  • From the point where the two trails split, you may add on one more loop, or a second loop to make a figure 8. One extra loop adds 1 mile to the hike. Adding on the second loop is an additional 1.7 miles (2.7 miles altogether). These sections will be downhill. The first loop goes down 200 feet in elevation and the second loop an additional 100 feet.
  • As indicated on the lower right of the map, this trail system can also be accessed by parking on Aircraft Road. This is the same parking as used for our suggested Seven Falls trail, except that you would head north on the blue blazed trail to reach Bear Hill, instead of south to reach Seven Falls.


Interested in discovering your own off the beaten path hikes? The Connecticut Walk Book and interactive trail map at are excellent resources.  Continue to follow The Rockfall Foundation’s blog for more guided suggestions.  Check the website for your town’s land trust as well. For Middlesex Land Trust Properties, visit their Preserves & Maps webpage. Continue to follow The Rockfall Foundation’s blog for more guided suggestions.


Coronavirus & Tick Safety

  • When social distancing is in effect, give other hikers six feet of space. Do not touch other’s dogs and keep your own dogs on a leash. When stepping off trail to make room, be mindful of any flora underfoot and step on rocks where possible.
  • To prevent overcrowding and facilitate social distancing, hike during less popular times such as early mornings and weekdays. Even hiking in a rain jacket during light rain can be a rewarding experience.
  • Follow the Leave No Trace principles which have been updated for COVID-19. The document at the link offers important considerations, such as being prepared to use the bathroom outdoors and carrying out your own trash.
  • Ticks are active March to November. Wear long clothing, tuck pants into socks, wear a repellant on your skin and pretreat your hiking clothes with permethrin. Shower afterwards and launder clothing. Click here for information on identification of different ticks.


Contributed by Amanda Kenyon and Lucy Meigs.

Did you try this hike? Please leave us a comment below!

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Showing 5 comments
  • Michele

    Completed the Bear Hill Loop on July 4, 2020 in the AM. The Mtn. Laurel bloom was finished but the long tunnels Allow one to imagine the beauty when in bloom. It was a hot, humid day yet between the tree coverage, the stream & much pine on the ground, the heat didn’t penetrate nor was it buggy:) It was also VERY quiet, peaceful, well marked & maintained. The View from most rock outcropping was obscured due to the foliage, but again i can imagine it beautiful in the fall. Although the highlights were out of season, it was an enjoyable walk for a hot, humid summers day! Please know I am thankful for the good info provided to be made aware of Bear Hill together with the directions which made it a hassel free walk:)

    • Amanda Kenyon

      So glad you tried and enjoyed the hike! Definitely visit again in the fall and spring to see more views, and early June for the mountain laurel blossoms.

  • Lauren

    Thank goodness we found your amazing directions! Thank you for your work and photos, that would have been tricky as there were multiple blue trail markers going in different directions. What a beautiful hike.

    • Liz Britney

      We are so happy you found it helpful – this hike can definitely be confusing but as you found, definitely worth it! Hope you enjoyed the beautiful weather!

  • Suzanne OConnell

    Thanks for your directions and trail information. I took my dog for a walk this morning on the blue and yellow trails of the Katchen Coley Preserve. What a beautiful way to start the day.

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