4.9
(1452)
16,216
runners
00:58
7.48km
200m
Running
The Skyline Loop is a moderate jogging route in Blue Hills Reservation, covering 4.6 miles (7.5 km). You will gain 664 feet (202 metres) in elevation, with an estimated completion time of 57 minutes. This route offers a good workout for those looking for a quick but challenging run.
As you jog the Skyline Loop, you can expect varied terrain that transitions from paved sections to dirt and gravel paths. The route offers continuous panoramic views, including the Boston skyline from the Blue Hill Observatory. You will also encounter the Wolcott Path, a notable trail section that adds to the diverse experience.
This route starts near the Blue Hill Observatory. Parking is generally available at the trailhead, but it can fill up quickly during peak times. Always check local conditions before you go, especially for potential ice, mud, or gravel on the paths.
Last updated: March 7, 2026
Waypoints
Start point
Parking
Get Directions
383 m
Highlight (Segment) • Trail
Tip by
1.53 km
Highlight • Viewpoint
Tip by
6.66 km
Highlight (Segment) • Trail
Tip by
7.48 km
End point
Parking
Way Types & Surfaces
Way Types
5.25 km
1.40 km
413 m
390 m
Surfaces
4.60 km
2.35 km
504 m
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Elevation
Highest point (170 m)
Lowest point (70 m)
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Weather
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Sunday 5 July
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Additional weather tips
Max wind speed: 12.0 km/h
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This route was planned by komoot.
The Skyline Loop is approximately 7.5 km (4.6 miles) long. For jogging, it typically takes around 55 to 60 minutes to complete, depending on your pace and the challenging terrain. The total duration listed for this route is 3453 seconds, which is about 57 minutes.
The terrain on the Skyline Loop is varied and can be quite demanding. While some sections might be smoother, you can expect a mix of dirt and gravel paths, with more rocky and rugged parts as you ascend. There are also stone-carved staircases. Depending on the season, you might encounter ice, mud, or loose gravel. The initial grade from the parking lot can be steep.
This route is rated as 'moderate' in difficulty. While not extreme, its varied terrain, including steep sections and rocky paths, makes it more challenging than a casual jog. Beginners with some fitness might find it manageable, but it's best to be prepared for a steady climb and uneven surfaces.
The Skyline Loop offers continuous panoramic views and interesting landmarks. You'll pass along Summit Road and Wolcott Path. A major highlight is the Blue Hill Observatory and View of Boston Skyline, providing stunning vistas of the city and surrounding areas.
Yes, the route incorporates sections of several other trails. You will jog along parts of the Skyline Trail (42% of the route), the North Skyline Trail (24%), and the Breakneck Ledge Path (23%). It also briefly uses the Claire Saltonstall Bikeway (5%) and the Wolcott Path (23%).
The best time to jog the Skyline Loop is generally from late spring through early fall. During these months, the weather is more favorable, and the trails are less likely to be covered in snow or ice. Fall offers beautiful foliage, while spring and summer provide lush greenery. Always check local weather conditions before heading out.
Dogs are generally allowed on trails within the Blue Hills Reservation, but they must be kept on a leash at all times. Please ensure you clean up after your pet to help maintain the natural environment for everyone.
No, there are no entrance fees or permits required to access the trails within the Blue Hills Reservation, including the Skyline Loop. It is a public park managed by the Massachusetts Department of Conservation and Recreation (DCR).
The Skyline Loop typically starts near the Paradise Visitor Center area within the Blue Hills Reservation. There are designated parking lots available at the reservation. During peak times, especially on weekends, parking lots can fill up quickly, so arriving early is recommended.
The Blue Hills Reservation is home to various wildlife. Along the Skyline Loop, you might spot common animals such as deer, squirrels, chipmunks, and a variety of bird species. Keep an eye out, especially in quieter sections of the trail.
The Skyline Loop is a popular route due to its scenic views. If you're looking for a less crowded experience, consider visiting during off-peak hours (early mornings or weekdays) or exploring other trails within the vast Blue Hills Reservation. Many trails offer similar natural beauty, though perhaps without the same panoramic Boston skyline views.
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