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 loops around the outer edge of the western Middlesex Fells, with several steep climbs to rocky outcrops. DCR says the best views of Boston are from Wright's Tower. A short spur, the Bear Hill Trail, leads to Bear Hill Tower, which Friends of the Fells lists as currently closed. The Rock Circuit Trail is a separate loop in the eastern Fells, on the other side of I-93.

Distance, Elevation & Difficulty

• Distance: 7.6 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

DCR suggests starting from the Bellevue Pond, Long Pond or Sheepfold parking areas, all on the west side of the park. See our parking guide for where each lot is.

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:

• Views of Boston from the rocky outcrops, especially at Wright's Tower
• The Bear Hill Trail spur to Bear Hill Tower (currently closed)
• 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. To compare it with easier hikes, see our hiking guide.

Before heading out, review parking options and check hours & fees. The trail is open year-round and free to access.