Great Blue Hill via Skyline Trail
Great Blue Hill via Skyline Trail
4.7
(8899)
16,199
runners
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
Start point
Parking
Get Directions
577 m
Highlight • Summit
Tip by
2.59 km
Highlight • Summit
Tip by
4.88 km
End point
Parking
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
Highest point (170 m)
Lowest point (60 m)
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Weather
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.