Off the Beaten Path: Great Hill

With a lookout at about 600 feet above sea level, Great Hill offers a birds-eye-view of two bodies of water. In one glimpse you can see both the Connecticut River winding southward, as well as Great Hill Pond at the foot of the hill. The trail to Great Hill is the starting point of the 50-mile Shenipsit Trail that goes from East Hampton to Stafford, and an entry point for the Meshomasic State Forest, one of Connecticut’s oldest state forests. The hike to Great Hill Lookout is a steep, yet accessible walk. You may opt to use trekking poles for the descent, particularly in the fall with leaf cover on the trail, or other slick conditions. Hiking boots are recommended, as there are often muddy conditions at the lower part of the hill in the wet seasons. Please stay on the trail to avoid damaging vegetation.

Hike Overview
Total length: 1 mile, plus a longer option
Difficulty: Moderate
Type: Out-and-back with a longer loop option
Elevation change:  180 feet
Trail: Blue-blazed Shenipsit Trail

GPS link to trailhead on Gadpouch Road, East Hampton, CT

From Main St. in Portland, head east on Route 66 for 5 miles. At the intersection of Rts. 151 and 66, turn north onto Depot Hill Rd (left turn from Portland). Drive 0.8 miles then turn right onto Gadpouch Rd. Travel 0.6 miles to the trail head.

trail map
Reference Connecticut Walk Book, page 327, Map 20-SH-01 or interactive map.

Parking and the trail head are on the left side of the road. This hike begins on the clearly labeled blue blazed trail, pictured to the left of the car.

Follow the blue blazes. You’ll cross a stream that is dry in the summer, but is a muddy area in the spring.

Beyond this point, the trail begins to ascend steeply. Keep pressing on – you’re already half way there!

In 0.4 miles, reach a junction with a blue-white trail to the left and the blue trail to the right. Turn left for the blue-white spur trail to the lookout. (Note: Prior to this marked junction there is an unmarked, well-trodden cut-off that also takes you to the blue-white trail. If you accidentally landed on that trail, no problem, simply turn left to pick up the blue-white trail when you hit a junction.)

Follow the blue-white trail for a tenth of a mile. This trail ends at a lookout with the Connecticut River and Great Hill Pond in view.

After taking in the views, retrace your steps back up the blue-white spur trail. When you see the parallel blazes that look like an equal sign, it means that the spur trail ends. Here you will turn right onto the blue trail to return to your car. Alternatively, follow the instructions below for a longer loop.

Additional Option

This loop option uses a trail which doesn’t have blazes and can be a challenge to locate the turn. Once you find the turnoff for the trail, though, it is well packed and easy to follow. However, attempt this loop only if you have strong sense of distance and direction and/or are tracking your route with Alltrails. The route is recorded here. It is about 1.8 miles for the entire loop.

To make the loop, rather than turning right at the end of the blue-white trail after leaving the lookout, stay straight. This will get you back on the blue-blazed Shenipsit Trail, heading northbound. You’ll gradually climb in elevation along the ridgeline passing over the unmarked high point of Great Hill.

The blue trail begins a gradual descent with some small uphills. After about ¾ of a mile from leaving the lookout, you’ll hit a somewhat rocky downhill.

After that, the trail flattens for a few hundred feet. Now start looking for a compacted trail to the right.

Turn right here to begin a downhill ascent to your car. This return trail is not blazed.

Descend through the woods until it flattens out and you reach a meadow.

At the end of the meadow, turn right onto an old paved path. Follow this path until you reach your car.

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.

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

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Showing 2 comments
  • Elwin Guild

    Amanda, Great job of promoting the “back yard” I grew up in. Captioned photos are great.

    • Amanda Kenyon

      Thank you! It was interesting to discover this trail and be able to share it with folks who aren’t from East Hampton.

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