3.4
(20)
100
hikers
01:54
6.51km
170m
Hiking
The Skyline Loop is a fantastic easy hike that offers a refreshing escape into nature without demanding too much time or effort. You'll traverse pleasant woodland paths, leading you to the summit of Wolcott Hill, where you can enjoy the fresh air and surrounding scenery. The highlight is undoubtedly the…
Last updated: June 9, 2026
Tips
Your route passes through protected areas
Please check local regulations for:
Waypoints
Start point
Parking
Get Directions
1.24 km
Hemenway Hill
Peak
2.03 km
Highlight • Summit
Tip by
2.77 km
Highlight • Viewpoint
Tip by
6.51 km
End point
Way Types & Surfaces
Way Types
4.31 km
2.21 km
Surfaces
4.21 km
1.51 km
401 m
399 m
Sign up to see more specific route details
Sign up for free
Elevation
Sign up to see more specific route details
Sign up for free
Weather
Powered by Foreca
Today
Wednesday 8 July
27°C
15°C
0 %
Additional weather tips
Max wind speed: 9.0 km/h
to get more detailed weather forecasts along your route
This route was planned by komoot.
The Skyline Loop offers a varied hiking experience. While generally considered easy, you'll encounter sections with natural paths, some rocky areas, and gentle inclines. It's suitable for most hikers looking for a pleasant outdoor walk.
Yes, dogs are generally welcome on trails within the Blue Hills Reservation, including the Skyline Loop. However, they must be kept on a leash at all times to protect wildlife and ensure a pleasant experience for all visitors.
The Skyline Loop can be enjoyed year-round. Spring offers fresh greenery and blooming wildflowers, while autumn provides stunning fall foliage. Summer is popular for its warm weather, and winter can be beautiful for snowshoeing or cross-country skiing, though conditions may vary.
No, there are no entrance fees or permits required to access the Blue Hills Reservation or hike the Skyline Loop. It is free and open to the public.
The trail offers several points of interest. You'll pass by Wolcott Hill, which provides some nice views. Another highlight is the Blue Hill Observatory and View of Boston Skyline, offering expansive vistas on a clear day.
Parking is available at various access points around the Blue Hills Reservation. Specific trailheads often have dedicated parking lots. It's advisable to check a map of the reservation for the most convenient parking near your desired starting point for the Skyline Loop.
Yes, the route also passes through sections of the Skyline Trail, North Skyline Trail, Wolcott Path, and Coon Hollow Path, offering opportunities to explore other parts of the Blue Hills Reservation.
Absolutely! With an 'easy' difficulty rating, a distance of approximately 6.5 km, and moderate elevation gain, the Skyline Loop is a great option for beginners or those looking for a relaxed hike.
The Blue Hills Reservation is home to various wildlife. You might spot common forest animals like squirrels, chipmunks, and a variety of birds. Deer are also frequently seen in the area. Remember to observe from a distance and not disturb them.
On average, hikers can expect to complete the Skyline Loop in about 1 hour and 53 minutes. This duration can vary depending on your pace, stops for views, and trail conditions.
While the trail itself does not have dedicated restrooms or water fountains, facilities may be available at visitor centers or main parking areas within the Blue Hills Reservation. It's always best to carry enough water for your hike.
For this easy loop, comfortable hiking shoes, water, and appropriate clothing for the weather are recommended. A small backpack for snacks and a camera to capture the views, especially from the Blue Hill Observatory, would also be beneficial.
Comments
Want to know more?
Sign up for a free komoot account to join the conversation.
Sign up for free