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Routes
Running trails & routes
United States
Massachusetts
Norfolk County
Milton

Skyline Loop

Moderate

4.9

(1452)

16,216

runners

Skyline Loop

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.

What to expect on Skyline Loop

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.

Planning your visit

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.

Trail details

  • Distance: 4.6 miles (7.5 km)
  • Elevation gain: 664 feet (202 metres)
  • Difficulty: moderate
  • Estimated time: 57 minutes

Last updated: March 7, 2026

Waypoints

A

Start point

Parking

Get Directions

1

383 m

Summit Road

Highlight (Segment) • Trail

Sightseeing, great view, awesome

Tip by

2

1.53 km

Take a hike to the summit of Great Blue Hill and the observation tower close by that offers a stunning 270° view of Boston, its harbour and to the South Shore. The 35-foot stone structure was built by the Civilian Conservation Corps between 1933 and 1944.

Tip by

3

6.66 km

Wolcott Path

Highlight (Segment) • Trail

This path is well-maintained and easy to navigate, surrounded by the most beautiful pine and hemlock trees. If you enjoy running on flat and wide-open spaces instead of challenging rocky terrain, this trail is perfect for you.

Tip by

B

7.48 km

End point

Parking

Loading

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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (170 m)

Lowest point (70 m)

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Weather

Powered by Foreca

Today

Sunday 5 July

30°C

20°C

0 %

Additional weather tips

Max wind speed: 12.0 km/h

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Frequently Asked Questions

How long does it typically take to jog the Skyline Loop?

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.

What is the terrain like on this route?

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.

Is the Skyline Loop suitable for beginners?

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.

What can I see along the route?

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.

Does the trail intersect other well-known paths?

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%).

What is the best time of year to jog this loop?

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.

Is the Skyline Loop dog-friendly?

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.

Do I need a permit or pay an entrance fee for the Blue Hills Reservation?

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).

Where is the best place to park for the Skyline Loop?

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.

What wildlife can I expect to see along the way?

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.

Are there any less crowded alternatives to this route?

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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