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Hiking trails & Routes
United States
Massachusetts
Norfolk County
Milton

North Skyline Trail

Easy

4.8

(9386)

9,387

hikers

North Skyline Trail

00:47

2.32km

150m

Hiking

The North Skyline Trail offers a refreshing, easy hike that quickly delivers on scenic rewards. You'll traverse gentle slopes, passing over Hancock Hill and Wolcott Hill, before reaching the iconic Blue Hill Observatory. From there, you can soak in expansive panoramic views, including a clear sight of the Boston skyline,…

Last updated: June 9, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Waypoints

A

Start point

Parking

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1

580 m

Hancock Hill

Highlight • Summit

Hancock Hill may not be the tallest or most popular summit in the reservation, but its tree-covered peak offers some of the most stunning views of Downtown Boston. Unlike other …

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1.02 km

Hemenway Hill

Peak

3

1.81 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 …

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B

2.32 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 …

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Way Types & Surfaces

Way Types

2.23 km

< 100 m

< 100 m

Surfaces

2.21 km

< 100 m

< 100 m

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Elevation

Elevation

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Weather

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Thursday 9 July

33°C

18°C

-- %

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Frequently Asked Questions

What is the difficulty level of the North Skyline Trail?

The North Skyline Trail is considered an easy hike. It covers a distance of approximately 2.3 kilometers (1.4 miles) with a moderate elevation gain of about 150 meters (492 feet), making it suitable for most hikers.

How long does it typically take to complete this hike?

Hikers can generally complete the North Skyline Trail in about 45-50 minutes, depending on their pace and how often they stop to enjoy the views.

Are dogs allowed on the North Skyline Trail?

Yes, dogs are generally permitted on trails within the Blue Hills Reservation, including the North Skyline Trail. Please ensure your dog is kept on a leash and that you clean up after them.

What are the parking options and trailhead access for the North Skyline Trail?

Specific parking details for the North Skyline Trailhead within the Blue Hills Reservation can vary. It's best to check the Blue Hills Reservation official website or local signage for the most current information on designated parking areas and access points.

Are there any permits or entrance fees required to hike in Blue Hills Reservation?

Generally, there are no entrance fees or permits required for day-use hiking in 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 updates or specific regulations that might apply.

What is the best time of year to hike the North Skyline Trail?

The North Skyline Trail is enjoyable year-round. Spring offers lush greenery, summer provides warm weather, and autumn showcases beautiful fall foliage. Winter hiking is also possible, but be prepared for potentially icy or snowy conditions.

What can I see along the route?

Along the North Skyline Trail, you can enjoy several notable points of interest. These include Hancock Hill, Wolcott Hill, and the Blue Hill Observatory and View of Boston Skyline, offering expansive views.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the Skyline Trail, Wolcott Path, and other segments of the North Skyline Trail itself, offering opportunities to extend your hike.

Is the North Skyline Trail suitable for beginners or families with children?

Given its 'easy' difficulty rating, relatively short distance, and moderate elevation gain, the North Skyline Trail is generally well-suited for beginners and families with children. It's a great option for a pleasant outdoor experience.

What kind of terrain can I expect on the North Skyline Trail?

The trail features varied terrain typical of the Blue Hills Reservation, which may include natural ground, some rocky sections, and potentially exposed areas. Comfortable hiking shoes are recommended.

Are there any facilities or water sources available on the trail?

As a relatively short trail, there are typically no dedicated facilities or water sources directly on the North Skyline Trail itself. It's advisable to bring your own water and any other necessities for your hike.

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