4.8
(9386)
9,387
hikers
00:47
2.32km
150m
Hiking
The North Skyline Trail offers a refreshing, easy hike that quickly delivers on scenic rewards. You'll traverse gentle slopes, passing over Hancock Hill and Wolcott Hill, before reaching the iconic Blue Hill Observatory. From there, you can soak in expansive panoramic views, including a clear sight of the Boston skyline,…
Last updated: June 9, 2026
Tips
Your route passes through a protected area
Please check local regulations for:
Waypoints
Start point
Parking
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580 m
Highlight • Summit
Tip by
1.02 km
Hemenway Hill
Peak
1.81 km
Highlight • Summit
Tip by
2.32 km
Highlight • Viewpoint
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Way Types & Surfaces
Way Types
2.23 km
< 100 m
< 100 m
Surfaces
2.21 km
< 100 m
< 100 m
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Elevation
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Thursday 9 July
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This route was planned by komoot.
The North Skyline Trail is considered an easy hike. It covers a distance of approximately 2.3 kilometers (1.4 miles) with a moderate elevation gain of about 150 meters (492 feet), making it suitable for most hikers.
Hikers can generally complete the North Skyline Trail in about 45-50 minutes, depending on their pace and how often they stop to enjoy the views.
Yes, dogs are generally permitted on trails within the Blue Hills Reservation, including the North Skyline Trail. Please ensure your dog is kept on a leash and that you clean up after them.
Specific parking details for the North Skyline Trailhead within the Blue Hills Reservation can vary. It's best to check the Blue Hills Reservation official website or local signage for the most current information on designated parking areas and access points.
Generally, there are no entrance fees or permits required for day-use hiking in the Blue Hills Reservation. However, it's always a good idea to check the official Massachusetts Department of Conservation and Recreation (DCR) website for any updates or specific regulations that might apply.
The North Skyline Trail is enjoyable year-round. Spring offers lush greenery, summer provides warm weather, and autumn showcases beautiful fall foliage. Winter hiking is also possible, but be prepared for potentially icy or snowy conditions.
Along the North Skyline Trail, you can enjoy several notable points of interest. These include Hancock Hill, Wolcott Hill, and the Blue Hill Observatory and View of Boston Skyline, offering expansive views.
Yes, the route also passes through sections of the Skyline Trail, Wolcott Path, and other segments of the North Skyline Trail itself, offering opportunities to extend your hike.
Given its 'easy' difficulty rating, relatively short distance, and moderate elevation gain, the North Skyline Trail is generally well-suited for beginners and families with children. It's a great option for a pleasant outdoor experience.
The trail features varied terrain typical of the Blue Hills Reservation, which may include natural ground, some rocky sections, and potentially exposed areas. Comfortable hiking shoes are recommended.
As a relatively short trail, there are typically no dedicated facilities or water sources directly on the North Skyline Trail itself. It's advisable to bring your own water and any other necessities for your hike.
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