Hiking at Middlesex Fells Reservation
Middlesex Fells Reservation packs over 100+ miles of trails into 2,575 acres of rocky forest, ponds, and ridgelines just outside Boston. Whether you're looking for a quick walk or a full-day challenge, the Fells has a trail for every level.
Trail Overview
Hiking trails at Middlesex Fells range from flat, easy paths around the reservation's ponds to rugged ridge climbs with significant elevation gain. Most trails are natural surface — expect rocks, roots, and uneven terrain throughout. Sturdy footwear is recommended for all but the most casual walks.
Best Hiking Trails at Middlesex Fells
Skyline Trail
The Skyline Trail is the signature hike of the Fells — a 6.9-mile loop over rocky ridges and forested summits with panoramic views. Marked with white blazes. Difficulty: Challenging.
Rock Circuit Trail
The Rock Circuit Trail is a 3.7-mile loop through the rocky eastern Fells near Melrose, passing granite outcrops like Melrose Rock, Black Rock, and Pinnacle Rock. Marked with white blazes. Difficulty: Moderate to challenging.
Hiking to Bear Hill Tower
Many hikers head for Bear Hill Tower at the Bear Hill summit, which offers 360-degree views, including the Boston skyline on clear days. The Skyline Trail, via the Bear Hill Trail spur, provides a route to the summit.
Trail Rules & Etiquette
- Dogs must be on a leash on all hiking trails
- Stay on marked trails to protect vegetation and prevent erosion
- Pack out all trash
- Yield to uphill hikers on steep sections
- Horses have right of way on multi-use trails
Getting There & Parking
The most popular trailhead is the South Border Road parking lot in Medford. The Bear Hill lot in Stoneham is a good alternative when South Border Road is full. See our full Parking & Directions guide for locations and weekend tips.
Trail Map
For a complete map of all hiking trails at Middlesex Fells Reservation, visit our Trail Map page.
The reservation is open year-round. See Hours & Fees for seasonal access information.