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Routes
Running trails & routes
United States
Massachusetts
Norfolk County
Milton

Great Blue Hill via Skyline Trail

Moderate

4.7

(8899)

16,199

runners

Great Blue Hill via Skyline Trail

00:39

4.88km

180m

Running

The Great Blue Hill via Skyline Trail is a 3.0 miles (4.9 km) jogging route rated moderate. You will gain 580 feet (177 metres) over an estimated 39 minutes, offering a rugged and scenic experience in the Blue Hills Reservation. This route is known for its challenging terrain and rewarding…

Last updated: April 23, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Blue Hills Reservation

Waypoints

A

Start point

Parking

Get Directions

1

577 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 …

Tip by

2

2.59 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

4.88 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

2.63 km

2.01 km

183 m

< 100 m

Surfaces

4.63 km

< 100 m

< 100 m

< 100 m

< 100 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 (60 m)

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Weather

Powered by Foreca

Today

Tuesday 19 May

36°C

19°C

30 %

Additional weather tips

Max wind speed: 21.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the terrain like on the Great Blue Hill via Skyline Trail?

The terrain is notably rugged, featuring rocky ascents, steep sections, and technical scrambles. You'll encounter pine paths, stone steps, and slabs, with roots often present. Good balance and agility are essential for navigating these demanding sections.

How long does it typically take to jog this route?

The route is approximately 4.88 km (3 miles) long and typically takes around 39 minutes to jog, depending on your pace and the technical nature of the trail.

Is the Great Blue Hill via Skyline Trail suitable for beginners?

This trail is rated as moderate difficulty for jogging. Due to its significant elevation changes, rocky sections, and technical scrambles, it requires good fitness and sure-footedness. Beginners might find it challenging.

What are the main viewpoints or landmarks along the trail?

Key highlights include Hancock Hill and the Great Blue Hill Summit. From the historic Eliot Observation Tower at the summit, you can enjoy panoramic 360-degree views of the Boston skyline and Harbor Islands. The trail also passes the oldest continuously used weather station in North America.

What kind of scenery can I expect on this route?

You'll jog through dense forests with towering eastern white pines, oaks, and hickories. The trail offers diverse scenery, including mountain laurel-covered slopes and an Atlantic cedar swamp, culminating in the expansive views from the summit.

Where can I park for the Great Blue Hill via Skyline Trail?

Parking is available at various trailheads within the Blue Hills Reservation. It's advisable to check the official Massachusetts DCR website for specific parking lot locations and capacity, especially during peak times.

Is the Great Blue Hill via Skyline Trail dog-friendly?

Yes, dogs are generally allowed on trails within the Blue Hills Reservation, but they must be kept on a leash at all times. Please ensure your dog is capable of handling the rugged and rocky terrain.

Are there any permits or entrance fees for the Blue Hills Reservation?

There are typically no entrance fees or permits required for general access to the Blue Hills Reservation trails. However, it's always a good idea to check the official mass.gov website for any updated regulations or specific event requirements.

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

Spring and fall offer pleasant temperatures and beautiful foliage, making them ideal. Summer can be warm, but you might find wild blueberries along the trail. Winter jogging is possible but requires appropriate gear for potentially icy or snowy conditions.

Does the Great Blue Hill via Skyline Trail connect with other paths?

Yes, the route is part of a larger network. While primarily following the Skyline Trail, it also passes through sections of the North Skyline Trail, Coon Hollow Path, Wolcott Path, and Skyline Trail South.

What should I wear or bring for jogging on this trail?

Given the rocky and uneven terrain, sturdy jogging shoes with good ankle support and grip are highly recommended. Layers of clothing are advisable, especially in cooler months, and always carry water, as there are no water sources directly on the trail.

Are there places to eat or stay near the Blue Hills Reservation?

Yes, the Blue Hills Reservation is conveniently located near several towns like Milton, Canton, and Randolph, which offer various cafes, pubs, restaurants, and accommodation options for visitors.

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