Massachusetts trails · Skyline Trail
Skyline Trail
A 4.4-mile out-and-back in Massachusetts, with 415 ft of climbing. Reaches Nahanton Hill and other lake/pass/summit destinations. Managed by BLUE HILLS RESERVATION.
Elevation profile
The climbing is spread fairly evenly along the route. It gives back about 919 ft along the way, so it rolls rather than climbing steadily.
3-D terrain
USGS 3DEP ELEVATION × ESRI WORLD IMAGERY · VERTICAL ×1.5
Reaches
- Nahanton Hill (summit)
- Buck Hill (summit)
- The Crags (summit)
- Chickatawbut Hill (summit)
- Wampatuck Hill (summit)
- Tucker Hill (summit)
- Kitchamakin Hill (summit)
- Slide Notch (pass)
- Babel Rock (summit)
- Blue Hills Reservoir (lake)
Getting there
SKYLINE TRAIL access — parking nearby. About 16 min drive (9 mi) from Boston. 42.23373, -71.02924 · directions
Daylight at the trailhead
On October 14, 2026 — the day this page was generated — first light reaches this trailhead at 6:27 a.m., the sun rises at 6:55 a.m. and sets at 6:04 p.m., and the last usable light fades about 6:32 p.m. (EDT) — 11 h 09 min of daylight. At about 2.7 mph plus 30 minutes per 1,000 feet of climbing, the 8.9-mile round trip takes roughly 3 h 42 min, so leaving the trailhead at sunrise puts you back around 10:37 a.m. — 7 h 27 min before sunset.
Loop options
- Skyline Trail + Unnamed trail + Reservoir Trail — 1.3 mi loop, 145 ft gain
- Unnamed trail + Skyline Trail + Reservoir Trail — 1.5 mi loop, 280 ft gain
Nearby trails
- Mass Central/Wayside Rail Trail — 13.7 mi
- Rock Circuit Trail — 14.4 mi
- Bay Circuit Trail — 16.0 mi
- Tri-Community Bikeway — 20.0 mi