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Routes
Hiking trails & Routes
United States
Massachusetts
Norfolk County
Milton

Skyline Loop

Easy

3.4

(20)

100

hikers

Skyline Loop

01:54

6.51km

170m

Hiking

The Skyline Loop is a fantastic easy hike that offers a refreshing escape into nature without demanding too much time or effort. You'll traverse pleasant woodland paths, leading you to the summit of Wolcott Hill, where you can enjoy the fresh air and surrounding scenery. The highlight is undoubtedly the…

Last updated: June 9, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Waypoints

A

Start point

Parking

Get Directions

1.24 km

Hemenway Hill

Peak

2

2.03 km

Wolcott Hill

Highlight • Summit

Although there are no far-reaching views from Wolcott Hill, it's still one of the taller peaks in the Blue Hills Reservation, standing at 133m (433ft).

As you wander through, you …

Tip by

3

2.77 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 …

Tip by

B

6.51 km

End point

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Way Types & Surfaces

Way Types

4.31 km

2.21 km

Surfaces

4.21 km

1.51 km

401 m

399 m

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Elevation

Elevation

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Weather

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Today

Wednesday 8 July

27°C

15°C

0 %

Additional weather tips

Max wind speed: 9.0 km/h

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Frequently Asked Questions

What is the terrain like on the Skyline Loop?

The Skyline Loop offers a varied hiking experience. While generally considered easy, you'll encounter sections with natural paths, some rocky areas, and gentle inclines. It's suitable for most hikers looking for a pleasant outdoor walk.

Are dogs allowed on the Skyline Loop trail?

Yes, dogs are generally welcome on trails within the Blue Hills Reservation, including the Skyline Loop. However, they must be kept on a leash at all times to protect wildlife and ensure a pleasant experience for all visitors.

What is the best time of year to hike this route?

The Skyline Loop can be enjoyed year-round. Spring offers fresh greenery and blooming wildflowers, while autumn provides stunning fall foliage. Summer is popular for its warm weather, and winter can be beautiful for snowshoeing or cross-country skiing, though conditions may vary.

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 Blue Hills Reservation or hike the Skyline Loop. It is free and open to the public.

What can I see along the route?

The trail offers several points of interest. You'll pass by Wolcott Hill, which provides some nice views. Another highlight is the Blue Hill Observatory and View of Boston Skyline, offering expansive vistas on a clear day.

Where can I park to access the Skyline Loop?

Parking is available at various access points around the Blue Hills Reservation. Specific trailheads often have dedicated parking lots. It's advisable to check a map of the reservation for the most convenient parking near your desired starting point for the Skyline Loop.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the Skyline Trail, North Skyline Trail, Wolcott Path, and Coon Hollow Path, offering opportunities to explore other parts of the Blue Hills Reservation.

Is the Skyline Loop suitable for beginner hikers?

Absolutely! With an 'easy' difficulty rating, a distance of approximately 6.5 km, and moderate elevation gain, the Skyline Loop is a great option for beginners or those looking for a relaxed hike.

What kind of wildlife might I see on the trail?

The Blue Hills Reservation is home to various wildlife. You might spot common forest animals like squirrels, chipmunks, and a variety of birds. Deer are also frequently seen in the area. Remember to observe from a distance and not disturb them.

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

On average, hikers can expect to complete the Skyline Loop in about 1 hour and 53 minutes. This duration can vary depending on your pace, stops for views, and trail conditions.

Are there any facilities like restrooms or water sources along the trail?

While the trail itself does not have dedicated restrooms or water fountains, facilities may be available at visitor centers or main parking areas within the Blue Hills Reservation. It's always best to carry enough water for your hike.

What should I bring for a hike on the Skyline Loop?

For this easy loop, comfortable hiking shoes, water, and appropriate clothing for the weather are recommended. A small backpack for snacks and a camera to capture the views, especially from the Blue Hill Observatory, would also be beneficial.

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