Skyline Trail
- 7.3 mi
- loop
- 719 ft
- climb
- 286 ft
- high point
- Loop
- route
- Jun–Oct
- best months
Skyline Trail is a 7.3-mile loop in Massachusetts, about 0.8 miles from Winchester Highlands. The route rises from a low point of 98 feet to a high of 286 feet, with a total elevation gain of 719 feet. The climb is steady, and the steepest stretch comes at about 3 miles in, where the grade reaches 9 percent. The trail is rated easy, and the trip is estimated to take about 3 hours. Late spring and early fall are the most comfortable times to go. Typical averages from a nearby weather station in Reading show May highs around 70°F and September highs around 75°F, with September also seeing the fewest wet days of the year. Bikes are not allowed on this trail. Several other routes start close by, including Dike Road at 0.1 mile and Reservoir Trail at 0.2 mile. Climbers can find Cheers about 0.4 mile away, and Long Pond Nature Trail is roughly 0.9 mile off.
- Dike RoadHiking0.1 mi
- Reservoir TrailHiking0.2 mi
- Dark Hollow Pond TrailHiking0.2 mi
- CheersRock climbing0.4 mi
- South OverhangRock climbing0.8 mi
Long Pond Nature TrailHikingPhoto: cofluoxetine, CC BY 2.0 (via Flickr)0.9 mi- Deer Hill BoulderRock climbing1 mi
Shawsheen RiverCanoeingPhoto: John Phelan, CC BY 3.0 (via Wikimedia Commons)8 mi
Source: Roamze catalog (indexable pages within 10 miles, PostGIS distance)
- Long Pond Nature TrailHiking · ~2 min drivePhoto: cofluoxetine, CC BY 2.0 (via Flickr)
Rock Circuit TrailHiking · ~4 min drivePhoto: isforinsects, CC BY-SA 2.0 (via Flickr)- Boston HarborwalkHiking · ~10 min drive
Nanepashemet RoadHiking · ~2 min drivePhoto: niklas.tenhaef1, CC BY-SA 2.0 (via Flickr)
Western GreenwayHiking · ~11 min drivePhoto: ethan.long, CC BY-SA 2.0 (via Flickr)
East Dam RoadHiking · ~3 min drivePhoto: Ktr101, CC BY-SA 2.0 (via Flickr)- Reservoir TrailHiking · Next door
Hemlock Pool PathHiking · ~3 min drivePhoto: ethan.long, CC BY-SA 2.0 (via Flickr)- Crystal Spring TrailHiking · ~2 min drive
- East PathHiking · ~4 min drivePhoto: ethan.long, CC BY-SA 2.0 (via Flickr)
Also worth it near here
Hemlock Pool at Middlesex FellsRock climbing · ~3 min drivePhoto: Karlunun, CC BY-SA 4.0 (via Wikimedia Commons)
Waitts MountainSummit · ~5 min drivePhoto: Thea Prum from Boston, USA, CC BY-SA 2.0 (via Wikimedia Commons)- Spy Pond Boat LaunchBoat launch · ~7 min drive
- Lake QuannapowittLake fishing · ~8 min drive
Best time to visit Skyline Trail
Best months: June–October. Best months have typical highs of 55–85 °F, lows of 30 °F or warmer (32 °F where the station doesn't record snow), at most one snowy day and no more than 12 wet days.
Jan
38° / 19°
12 wet · 8 snow
Feb
40° / 20°
11 wet · 7 snow
Mar
48° / 27°
13 wet · 6 snow
Apr
60° / 37°
13 wet · 1 snow
May
70° / 47°
13 wet
Jun
78° / 56°
12 wet
Jul
84° / 63°
11 wet
Aug
82° / 61°
10 wet
Sep
75° / 53°
9 wet
Oct
64° / 42°
11 wet
Nov
53° / 32°
11 wet · 2 snow
Dec
43° / 24°
12 wet · 5 snow
Typical high / low (°F) and days with rain or snow, 1991–2020. Measured at Reading, MA, 4.1 mi away at 110 ft. Source: NOAA NCEI U.S. Climate Normals 1991–2020.
Route details
- Distance
- 7.3 mi
- Climbing
- About 719 ft
- Summit
- 244 ft
- Difficulty
- Easy
- Time
- About 2.5 hours
Questions about this route
How long is the Skyline Trail on Pine Hill?
About 7.3 mi.
How much elevation gain is on the Skyline Trail?
About 719 ft of climbing round trip.
How hard is the Skyline Trail?
It is rated easy.
How long does the Skyline Trail take?
About 2.5 hours round trip.
Conditions and forecast on Pine Hill
Daily highs and lows, wind and the chance of precipitation at the summit and route start for the next 7 days, from the Open-Meteo model.
Map and trail data © OpenStreetMap contributors
