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Routes
Bike touring routes & trails
United States
Massachusetts
Norfolk County
Milton

Blue Hills Skyline Loop

Moderate

2.5

(13)

91

riders

Blue Hills Skyline Loop

01:16

14.0km

220m

Cycling

The Blue Hills Skyline Loop is a challenging hiking trail with panoramic Boston views, not suitable for touring cycling due to rugged terrai

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Blue Hills Reservation

Waypoints

A

Start point

Parking

Get Directions

1

940 m

Breeze Hill

Highlight • Summit

Breeze Hill, a Quincy, Norfolk, Massachusetts peak with a 276-foot elevation, offers an accessible trail in Blue Hills Reservation. Delight in scenic vistas and lush forests while exploring this peak.

Tip by

2

7.39 km

Walcott Path (Gravel Road)

Highlight (Segment) • Trail

Great gravel road through the forest. There is elevation change when riding this road: however, it is well graded and a good surface. It is worth the effort once you get a view from the summit of Great Blue Hill.

Tip by

3

9.94 km

Great Blue Hill Summit

Highlight • Summit

Ride your bike up the Big Blue Hill, and get a few minutes rest, and the view as a reward!

Tip by

B

14.0 km

End point

Parking

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Way Types & Surfaces

Way Types

7.37 km

2.80 km

2.75 km

1.05 km

< 100 m

Surfaces

8.42 km

4.11 km

1.50 km

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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 (180 m)

Lowest point (50 m)

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Weather

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Today

Wednesday 6 May

21°C

13°C

68 %

Additional weather tips

Max wind speed: 27.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Is the Blue Hills Skyline Loop suitable for touring cycling?

No, the Blue Hills Skyline Loop is not suitable for touring cycling. It is primarily a challenging hiking trail known for its rugged, rocky, and uneven terrain, including steep climbs and descents. Attempting to navigate it on a touring bicycle would be extremely difficult, if not impossible, and is not recommended.

What is the terrain like on this trail?

The terrain on the Blue Hills Skyline Loop is rugged and challenging. Expect rocky sections, uneven ground, and numerous steep ascents and descents. It often requires steady footing and can be strenuous even for hikers.

Are there any cycling alternatives within the Blue Hills Reservation?

Yes, while the Skyline Loop itself is not for touring bikes, the wider Blue Hills Reservation offers other cycling opportunities. You can find a network of trails suitable for mountain biking, including smooth pathways, doubletrack, singletrack, and fire roads. There are also designated road cycling loops within the area, some of which are almost entirely paved.

What can I see along the route?

Despite its challenging terrain, the route offers rewarding views. You'll pass by notable points like Breeze Hill and the Great Blue Hill Summit. From various hilltop vistas, you can enjoy nearly 360-degree panoramic views, including the Boston skyline.

Where can I park to access the Blue Hills Skyline Loop?

Parking is available at various access points around the Blue Hills Reservation. For specific trailhead access to the Skyline Loop, it's best to consult a detailed map of the reservation to find the most convenient parking areas. Be aware that parking lots can fill up quickly, especially on weekends.

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

Generally, there are no entrance fees or permits required for day use of 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 updated regulations or specific activity permits, especially for larger groups or events.

Is the trail dog-friendly?

The Blue Hills Reservation is generally dog-friendly, but dogs must be kept on a leash at all times. Please ensure you clean up after your pet to help maintain the natural beauty of the area.

What is the best time of year to visit the Blue Hills Skyline Loop?

The Blue Hills Skyline Loop can be enjoyed year-round. Spring offers lush greenery, while autumn provides stunning fall foliage. Summer is popular but can be hot, and winter offers a unique, often snowy, experience, though conditions can be challenging. Always check weather conditions before heading out.

Does the trail intersect other well-known paths?

Yes, the route incorporates sections of several other paths within the reservation, including the Skyline Trail, Wolcott Path, Tucker Hill Path, Buck Hill Path, and Headquarters Path, among others.

How long does it typically take to complete the Blue Hills Skyline Loop on foot?

While the Komoot tour data suggests a duration for cycling, given the rugged and challenging hiking terrain, completing the 14 km Blue Hills Skyline Loop on foot typically takes significantly longer than the indicated cycling time. Hikers should plan for several hours, depending on their pace and how often they stop to enjoy the views.

Are there any specific viewpoints or landmarks along the trail?

Yes, the trail offers several rewarding viewpoints. From various high points, including near the Great Blue Hill Summit, you can enjoy expansive views of the surrounding landscape and the Boston skyline. Historical elements like Eliot Tower are also notable landmarks within the reservation.

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