Middlesex FellsReservation
Bear Hill Trail at Middlesex Fells Reservation — hero photo placeholder

Bear Hill Trail at Middlesex Fells Reservation

If you're looking for a short hike with a real payoff, Bear Hill is it. The trail to the summit is one of the more popular routes in the East Fells — and for good reason. At the top, you'll find the historic Bear Hill Observation Tower, open-air views of the Boston skyline, and easy connections to some of the best trails in the reservation.

It's also one of the most accessible starting points in the park. The Bear Hill parking lot off South Border Road is easy to find, well-marked, and puts you right at the trailhead.

Trail Overview

Bear Hill is the high point of the entire reservation. The trail gains elevation steadily from the parking lot, passing through rocky, forested terrain before opening up at the summit near the Observation Tower.

Trailheads & Parking

Bear Hill Parking Lot is the primary trailhead for this trail and one of the most commonly used lots in the East Fells. It's located off Fallon Road and gives you direct access to Bear Hill and the Skyline Trail.

For a full list of parking areas across the reservation, visit our Parking and Directions page.

What to Expect on the Trail

The hike to Bear Hill summit is relatively short but earns its moderate rating with rocky footing and a steady climb. The trail winds through the East Fells' characteristic terrain — dense mixed forest, granite outcroppings, and the occasional open ledge where you can catch your breath and take in the surroundings.

At the summit, you'll find the Bear Hill Observation Tower — a historic stone structure that's been part of the Fells landscape for over a century. Climb the tower for elevated views of the Boston skyline to the south and the wooded hills of the reservation spreading out in every direction. It's one of the better viewpoints in the park.

From the summit, the Skyline Trail continues west across the ridge. Many hikers use Bear Hill as a launching point for longer routes through the East and West Fells.

Bear Hill Observation Tower

The tower at Bear Hill's summit is known as Bear Hill Tower — not to be confused with Wright's Tower on Pine Hill in the western Fells. It's one of the lesser-known spots in Middlesex Fells. Built in the early 1900s, it's a short climb up the interior stairs to an open platform with panoramic views.

On a clear day you can see:

The tower is currently closed to climbing — DCR has fenced it off pending restoration — but the surrounding summit and grounds remain open during park hours at no charge. See our Observation Tower page for current status.

Connecting Trails

Bear Hill sits at a natural crossroads in the East Fells. From the summit or nearby junctions, you can connect to:

Tips Before You Go

More at Middlesex Fells