Skyline Trail at Middlesex Fells Reservation
The Skyline Trail is the longest and most scenic hiking trail at Middlesex Fells Reservation, tracing a rugged ridge through the western section of the park with panoramic views, rocky summits, and connections to some of the region's most rugged terrain. It's the signature hike of the Fells — steep, rocky, and worth the effort.
Trail Overview
The Skyline Trail is marked with white blazes and runs as a loop through the highest elevations of the western Middlesex Fells. It passes over multiple rocky summits including Bear Hill, where Bear Hill Tower offers 360-degree views on clear days. The trail connects to the Rock Circuit Trail at several points, making it easy to extend or shorten your hike.
Distance, Elevation & Difficulty
- Distance: 6.9 miles (loop)
- Elevation gain: ~800 feet
- Difficulty: Challenging
- Trail surface: Rocky ledge, rooted terrain, steep sections
- Blazes: White
The Skyline Trail is best suited for experienced hikers. The rocky and uneven terrain requires sturdy footwear and careful footing, especially on wet days.
Trailheads & Parking
The most common starting point is the South Border Road parking lot in Medford. The Bear Hill lot off Fallon Road in Stoneham also provides access. See our parking guide for lot locations and weekend arrival tips.
What to Expect on the Trail
The Skyline Trail has some of the best views near Boston. The trail climbs repeatedly over rocky ridges before descending into forested valleys, making for a varied and engaging hike from start to finish.
Highlights include:
- Summit views at Bear Hill and other high points along the ridge
- The historic Bear Hill Tower at Bear Hill summit
- Connections to the Rock Circuit Trail for shorter loop options
- Dense mixed forest with excellent fall foliage
Trail Map
For a full map of the Skyline Trail and connecting routes, visit our Trail Map page.
Before heading out, review parking options and check hours & fees. The trail is open year-round and free to access.