4.9
(6363)
16,707
runners
01:00
7.93km
150m
Running
Embark on the Blue Hills Skyline Loop, a moderate jogging route that covers 4.9 miles (7.9 km) and climbs 483 feet (147 metres) in about 1 hour. You will find yourself navigating rugged terrain with rocky paths and significant stone steps, often requiring agile rock scrambles. As you jog, the…
Last updated: April 23, 2026
Waypoints
Start point
Parking
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3.42 km
Highlight • Viewpoint
Tip by
7.93 km
End point
Parking
Way Types & Surfaces
Way Types
6.94 km
895 m
< 100 m
Surfaces
7.01 km
378 m
246 m
123 m
105 m
< 100 m
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Elevation
Highest point (130 m)
Lowest point (30 m)
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Monday 25 May
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This route was planned by komoot.
This loop is generally rated as moderate to strenuous for jogging due to its technical and rugged terrain. Expect rocky paths, significant stone steps, roots, and steep ascents and descents that often require rock scrambles. It's a demanding route that provides a rigorous workout, sometimes compared to trails in the White Mountains.
The komoot tour data suggests an average jogging duration of approximately 1 hour for the 7.9 km (4.9 miles) loop. However, given the technical terrain and significant elevation changes, individual times may vary based on fitness level and pace.
The terrain is highly varied and technical. You'll encounter rocky paths, numerous stone steps, slabs, and roots. There are steep sections requiring rock scrambles, demanding attention and agility. While some parts might be flatter or consist of pine paths, a considerable portion involves uneven and rugged footing.
A major highlight is the sweeping view of the Boston skyline, particularly from Great Blue Hill and the historic Eliot Observation Tower located atop it. You can find more details about this specific viewpoint here: View of Boston from Blue Hills Reservation. Beyond the cityscapes, you'll jog through dense hardwood forests, pine and hemlock stands, meadows, and past ponds.
Parking is available at various points around the Blue Hills Reservation. For specific trailhead access points, it's best to consult the official Blue Hills Reservation maps or local signage upon arrival. Arriving early, especially on weekends, is often recommended to secure a spot.
Yes, dogs are generally allowed on trails within the Blue Hills Reservation. However, they must be kept on a leash at all times. Given the technical nature of this loop, ensure your dog is capable of handling rocky and steep sections.
The trail offers different experiences throughout the year. Spring and fall provide pleasant temperatures and beautiful foliage. Summer can be warm and humid, while winter, especially with snow, can make the already technical terrain even more challenging, though some find running down the summit easier in snow. Always check trail conditions before heading out.
No, there are typically no entrance fees or permits required to access the trails within the Blue Hills Reservation. It is a public park managed by the Massachusetts Department of Conservation and Recreation (DCR).
Yes, the Blue Hills Skyline Loop utilizes and intersects with several other trails within the reservation. Notable sections include the Skyline Trail, Crags Foot Path, Pipe Line, Headquarters Path, and Murphy Path, among others. The main Skyline Loop is identifiable by blue blazes.
Given the trail's ruggedness and technical scrambles, many experienced joggers use this loop as a 'test run' for more challenging hikes in New England. If you're looking for a less crowded experience, consider starting your jog earlier in the morning or on a weekday. Also, be prepared for significant rock scrambling, especially on descents.