Skyline Trail (Middlesex Fells) Hiking Guide
The Skyline Trail traces the outer edge of the western Middlesex Fells, the half of the reservation west of I-93, in one long white-blazed loop. It wraps around the Winchester reservoirs, climbs onto one rocky knob after another, and passes Wright's Tower, a stone lookout with a view across the Boston basin. DCR rates it a difficult hike, and the constant up-and-down bears that out.
Three Sources, Three Distances
DCR's 2024 Fells map lists the Skyline at 7.6 miles and about five hours. The Friends of the Middlesex Fells give 6.9 miles. Hiking Project measures the loop at 12.1 kilometers, about 7.5 miles, with 258 meters (roughly 850 feet) of climbing and a maximum grade near 19 percent. Plan on most of a day at a relaxed pace. The trail is open to pedestrians only, so you will not share it with bikes, though it crosses the green Mountain Bike Loop and the orange Reservoir Trail many times.
Wright's Tower and the Southern Ridge
The highlight sits on the southeast side of the loop. Wright's Tower looks out over the Boston basin, and from its rock you can see the city skyline and the traffic on I-93 at the same time. DCR suggests reaching it from the parking pull-offs along South Border Road in Medford, such as the one at Bellevue Pond. Starting there puts the tower near the beginning or end of the day, whichever direction you choose.
Where to Start
Parking is free at every DCR lot in the Fells. Besides the South Border Road pull-offs, the Sheepfold lot on Route 28 is the most popular way in; Hiking Project calls it the easiest access and warns it gets crowded on weekends and after work. DCR notes the lot gates open at 9 a.m., and the reservation closes at sunset. Some reservoir land along the loop belongs to the Town of Winchester water supply and is posted no trespassing, so stay on the blazed route.
Dogs on the Skyline
The five-acre Sheepfold meadow is the Fells' one designated off-leash area, and dogs there must still be under voice control. Once you step onto the Skyline, dogs need to be on a leash. DCR limits each handler to four dogs and requires you to carry waste out if no trash can is available. Bear Hill Tower, reached by a short side trail, is closed, according to the Friends of the Fells.
Mud, Rock and Getting Lost
Many single-track sections are steep, rough and rocky, and DCR warns they can be slippery or muddy at any time of year. Avoid the trail after heavy rain. The bigger challenge is staying on route: dozens of fire roads and user-made paths cross the Skyline, and DCR asks hikers to stick to official trails while it closes the rest. Carry the map, and if you drift off course, the parallel Reservoir Trail or Mountain Bike Loop will usually lead you back.
Hiking tips for Skyline Trail (Middlesex Fells)
- Start from a South Border Road pull-off to reach Wright's Tower early.
- Go on a weekday or early morning to find space at the Sheepfold lot.
- Leash dogs once you leave the Sheepfold meadow; the trail is not off-leash.
- Stay off posted Winchester water-supply land along the reservoirs.
- Pack a map; the white blazes cross many unmarked paths.
Nearby trails to explore
- Rock Circuit Trail (Middlesex Fells)
- Walden Pond Path
- Breakheart Ridge Trail and Saugus River Loop
Hike this trail with TrailMates
Seven-plus miles of rock and reservoir views, all just north of the city. Use TrailMates to find Boston hikers heading to the Fells Skyline Trail. Download the TrailMates app to connect.