A Guide to Running Boston's Blue Hills Skyline Trail

Located just outside of Boston, the Blue Hills Skyline Trail takes runners on a nine-mile traverse across the heart of the Blue Hills Reservation and offers metropolitan New Englanders a classic trail run. With approximately 2,000 feet of elevation gain and some of the region’s most technical up-and-down terrain, it’s a great test-piece that’s well worth checking out.

If you are running the full traverse for the first time, it’s best to begin from the parking lot at Shea Rink in Quincy. From that trailhead, it’s easy to follow the Skyline’s rectangular blue-blazes, especially if you print a copy of the map ahead of time. Road crossings segment the Skyline into the six distinct sections, letting you break it up into bite-sized chunks:

Credit: John Dill
Credit: John Dill

The Opening Salvo

The first section—between Shea Rink and Wampatuck Road—is so short that I consider it my warm up. Through its flat single and double track, you’ll have breezed by St. Moritz Pond after just a few minutes and be preparing to cross Wampatuck Road.

The second section begins as the Skyline makes a sharp, well-marked southwest turn just after the road crossing. From there, the trail climbs gradually on rocky but runnable terrain, going past an old quarry and then to the summit of Rattlesnake Hill. After, the trail then quickly descends over some technical terrain, which usually has me regretting bypassing the easier way down on the runner’s right, before ascending up and over Wampatuck Hill to Chickatawbut Road.

Credit: John Dill
Credit: John Dill

The Crux

To Chickatawbut Hill

The next three sections put the meat on the Skyline’s bones. The first, easy to underestimate, traverses Nahanton, Kitchamkin, Fenno, and Chickatawbut Hills. Up to Chickatawbut Hill, a current Mass Audubon facility and former Nike missile base, the trail flows well and is runnable. Be mentally prepared, however, for the section’s up-and-down nature. Here, you’ll almost immediately be giving back (and then re-earning) all that hard-won elevation.

After Chickatawbut Hill, the Skyline has a lengthy descent to the Route 28 road crossing. A short portion goes down a rocky outcropping and requires careful route-finding, until you can escape to easier terrain in the woods on the runner’s right.

Credit: Bill Iliot
Credit: Bill Iliot

Fourth Section

Once you’ve made it across Route 28, the fourth section begins with one of the traverse’s steepest climbs. But, the ascent is well worth it, and I often find myself pausing momentarily on Buck Hill’s open summit to appreciate the fantastic 360-degree view.

Before you get too far, make sure to look back northeast at Boston Harbor and the city skyline. Then, run off Buck Hill, across North Boyce Hill, and up steep Tucker Hill, the final climb, before heading downhill to Hillside Street and Reservation Headquarters.

As the Skyline’s only facility beyond the halfway point, Reservation Headquarters has a seasonal outdoor water fountain and, during business hours, an indoor public bathroom.

Credit: John Dill
Credit: John Dill

North and South Skyline

From Headquarters, the Skyline temporarily splits into the North Skyline and the South Skyline, eventually rejoining near the summit of Great Blue Hill. Standing 635 feet tall, Great Blue Hill is the tallest point within 10 miles of the Atlantic Coast, south of Maine.

Of the two options, the North Skyline, with its traverse of Hancock, Hemingway, and Wolcott Hills, is a more aesthetically pleasing east-to-west route. It is also the more technical of the two, with a few short but steeper-than-you’d-expect-for-Greater-Boston descents.

Taking the North Skyline also allows you to run by the two most well-known attractions on Big Blue, the Eliot Tower and the Eliot Memorial Bridge, before the trail meets up with the South Skyline near the Blue Hill Meteorological Observatory. Both are named after Charles Eliot, the landscape architect who helped design many of Greater Boston’s parks. The Skyline then loops around the Observatory, the oldest continuously operating one in the country, before making a comparatively lengthy descent to the Route 28 road crossing.

The Final Sprint

Assuming you have some energy left, the Skyline’s final section is a good place to push it and try to surpass a personal record. In no time, you’ll dispatch Little Blue Hill, the section’s only climb, cross a side street, and be nearing the trail’s western-terminus. And, then, it’s over, ending anticlimactically at an unmarked finish line near an Interstate 95 on-ramp.

Credit: John Dill
Credit: John Dill

Skyline Loop

If you don’t have time for the full traverse or only have one car, the Skyline Loop (3.5 miles, with 800 feet of elevation gain) is a great alternative. It starts on the North Skyline at the Reservation Headquarters on Hillside Street, traverses west across Hancock, Hemingway, and Wolcott Hills as described above, and then meets with the South Skyline on Great Blue Hill.

The South Skyline brings you back east, eventually climbing Houghton Hill before dropping down to Hillside Street and then requiring a short jog back to Reservation Headquarters. And, with the multiplicity of trails leaving from this location, it’s easy to tack on extra mileage at the end if you are still feeling fresh.