Skyline Trail at Blue Hills Reservation

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Visit Blue Hills Reservation to hike its Skyline Trail, or the shorter Skyline Loop, to catch a panoramic view of Boston's city skyline.

Written by

Allie Aylward


9.0 miles

Destination Distance From Downtown

10.1 miles


3 of 5 diamonds

The Skyline Trail is accessible to beginners yet also suitable for hikers and runners looking to train for more difficult hikes. Its terrain includes a few rocky scrambles, which are easily conquered with careful footing.

Time To Complete

3 hours

Hikers should allot around 3.5 hours to complete the Skyline Trail's 9.0 mile route. For a shorter hike more manageable for families, opt for the Skyline Loop and allot 1.75 hours.


All Seasons

Open year round from dawn ’til dusk. Not surprisingly, this Boston-area favorite can become crowded on weekends, especially during the summer. Trail runners especially may prefer to avoid the peak hours for trail traffic — between 11:00 a.m. and 2:00 p.m.

Dog Friendly

On Leash Only

Fees Permits


Parking is free. No fees or permits are needed to hike or trail run. Camping overnight is only allowed in the cabins along Ponkapoag Pond. Call the Appalachian Mountain Club to reserve a cabin overnight at (781) 961-7007.

Topographical Map

Blue Hills Reservation



Spanning 7,000 acres across Milton, Canton, Quincy, Dedham, Randolph and Braintree is the historic Blue Hills Reservation, land set aside in 1893 for preservation and public recreation. The Skyline Trail, 9.0 miles long and marked with blue blazes, is one of the reservation’s longest and most popular trails. Many hikers complete the Skyline’s abbreviated version, The Skyline Loop (4.5 mi.), which includes two of the reservation’s main highlights: Eliot Tower and the Blue Hill Meteorological Observatory. With a number of overlooks for Kodak moments, varied terrain, clear signage and frequent trail markers, the Skyline Trail is suitable for nearly all outdoor enthusiasts.

What Makes It Great

The Skyline Trail’s proximity to the city and its namesake view of Boston’s skyline are its primary draw for hikers and trail runners — though the route certainly has more to offer. 

A series of rolling hills punctuate Skyline’s gradual slope to Great Blue Hill, the reservation’s highest peak at 635 ft. Built atop Great Blue Hill is Eliot Tower, an excellent vantage point from which to admire the city skyline and the surrounding Neponset River Valley. Also on Great Blue Hill’s summit is the historic Blue Hill Meteorological Observatory, a structure built in 1885 by Abbott Rotch. The observatory has been running since Rotch first built it, making it the oldest continuously-operated weather observatory in the country.

During July and August, the Skyline Trail is lined with wild lowbush blueberries. Smaller than the blueberries you’ll find in the grocery store, wild blueberries are flavorful and refreshing to munch while on the trail. A word of warning: exercise caution if foraging without a trusted edible plants guidebook — a poisonous plant with an appearance similar to lowbush blueberries is the Pokeweed Berry. While I did not see any pokeweed berries on the trail, it’s important to recognize their distinction.

A few sections of the Skyline Trail will require careful steps and scrambling, but this will come as no surprise to local hikers, as the rocky footing is characteristic of New England trails. Luckily, painful blisters will fall silent during the sections of the trail that fall under tree cover and are padded with pine needles. 

A summertime visit to the Skyline Trail also offers a side trip to the spring-fed Houghton’s Pond, where swimming on a hot day comes as a welcome respite. Houghton’s Pond is a short walk from the reservation’s headquarters, but is also accessible via trails surrounding the pond and via the parking area off Blue Hill River Road.

Who is Going to Love It

Though the trail is 9.0 miles from start to finish, the trail overlap and recommended “short cut” hikes, like the Skyline Loop, allow outdoor enthusiasts of all skill levels and time commitments to enjoy the Skyline Trail.

Despite its proximity to the Boston metro area, the Skyline Trail can feel as backwoods as remote trails in Central Massachusetts. The trail is ideal for city dwellers looking immerse themselves in nature, beginners who want to try out hiking, and experienced hikers and trail runners who want to train for more strenuous trails.

Directions, Parking, & Regulations

The trail is open from dawn 'til dusk and prohibits mountain biking. 

There are a number of parking areas from which to choose when visiting the Skyline Trail. If you wish to hike the entirety of the trail, you’ll need to park near Shea Rink in Quincy or at the opposite end of the trail, located at the base of the Blue Hill Ski area off Rt. 138 in Canton. Hikers that elect to take the popular Skyline Loop trail can find parking in two small lots near the reservation headquarters.

To get to a Skyline trailhead via public transit, take the Red Line to Ashmont Station then take the outbound #240 Bus to Randolph Avenue and Chickatawbut Road. From there it is a 1.0 mile walk to Blue Hills Headquarters where hikers can join the Skyline Trail. For detailed directions on how to reach the Eastern or Western origins of the Skyline Trail, see the reservation’s info sheet.

Maps are available at the Blue Hills Trailside Museum, located at 1904 Canton Ave. in Milton, as well as at the Reservation Headquarters, 695 Hillside St., Milton. 

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Blue Hills Reservation

695 Hillside St
Milton, MA, 02186
42.214471, -71.093704

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