Trail Running at the Middlesex Fells Reservation

March 18, 2019
trail running at middlesex fells
Bryan SchnittjerEven when it’s snowy, the author (center), rises with fellow dads Bryan (left) and Rob (right) for a Sunday morning, pre-dawn trail run in the Middlesex Fells Reservation.

For the last year at least, my Sunday morning alarm has gone off at 5:25 a.m. I roll out of bed, get dressed in the dark—quietly, so as not to wake the wife or kids—and collect several essentials: gloves, a headlamp, a water bottle, a nutrition bar, and any stocking hat or jacket I need, depending on the conditions. At 5:45 a.m. on the dot, my buddies Rob and Bryan pull up in front of my house, where we pile into Rob’s car and start driving. Our Sunday morning trail runs have become a lifeline for the three of us—all fathers in the trenches with young children—and we do not miss it for anything. We’re like the U.S. Postal Service: “neither rain nor snow nor heat nor gloom of night” can keep us off the pre-dawn trails.

Our destination is often the 2,575-acre Middlesex Fells Reservation, an expansive system of trails, fields, lakes, and hills that borders five towns—Medford, Winchester, Stoneham, Melrose, and Malden—just a few miles outside of Boston. In 1632, Gov. John Winthrop wrote about the area in his journal, describing a “very great pond…very thick with trees of pine and beech…and diverse small rocks standing up here and there in it.” Today, the Fells, maintained by the Massachusetts Department of Conservation and Recreation (DCR), is divided north-to-south by Interstate 93, creating two fairly distinct eastern and western sections.  Of the nine trails in the Fells, just one—the Cross Fells Trail—connects the two halves.

Taking Exit 33 off 93, we always follow the Roosevelt Circle roundabout to South Border Road in Medford, where we pull into the second parking area, across from Jeremiah Circle. (the larger Bellevue Pond parking area is usually closed before dawn) After switching on our headlamps and taking a last swig of water or coffee, we’re usually on the trail by 6:15 a.m.

We almost always head due east where we kick off the run with a steep ascent up rugged Pine Hill to Wright’s Tower, which affords an unmatched panorama of metro Boston—from Logan Airport in the Northeast to skyscrapers downtown to Cambridge and the western suburbs. On a clear day during the warmer months, the sun is just cracking the horizon as we summit Pine Hill, resulting in a spectacular reward indeed.

Our mission from there is typically to find water as quickly as possible. On the east portion of the Middlesex Fells, the trail system surrounds a reservoir maintained by the Town of Winchester. The trails immediately around and crossing the reservoir system are closed to the public. The Reservoir Trail, however, offers some water views and surrounds all three lake sections. Our path from the tower to the Reservoir Trail is sometimes meandering, but usually involves taking the Skyline Trail to East Dam Road, which eventually arrives at water. Once you’re on the Reservoir Trail headed north, the only (legal) ways to get back to where you parked are to do an out-and-back or to go clear around all three lakes. That route, not including the tower detour, is just over 5 miles total.

It is possible, however, to run in the Fells and never see water. Following the Cross Fells Trail to the Mountain Bike Loop and heading north along I-93 provides a challenging and rewarding out-and-back through the deep woods.

Similarly, the trails to the north and east of the reservoirs take you under a canopy of tall evergreens, where a bed of pine straw across much of the footpath makes for a luxuriously spongy ride. It’s here that we often wonder whether we’re steps from the concrete and steel of Boston or deep in the Cascades of the Pacific Northwest.

A few notes:

  • If you’re not looking for a rocky, hilly run, avoid the Skyline Trail and stick to Cross Fells, Long Pond, Reservoir, and the Mountain Bike Loop.
  • Your pace will depend heavily on the amount of snow/ice/mud on the trails. Keep in mind that because of the heavy tree cover in the Fells, snow and ice can remain on trails much longer than outside of the Reservation. MicroSpikes and YakTrax can really come in handy for winter traction.
  • Several of the main trails in the Fells become waterways in wet weather, resulting in a skating rink in many places when it’s cold. You always run at your own risk, but this is especially true in wintry conditions.
  • Overall, signage and blazes could be improved in the Middlesex Fells. Definitely acquaint yourself with a trail map before heading out or build in lots of time for getting lost, intentionally or unintentionally—if that’s your jam.
  • If you’re someone who runs with a dog, keep in mind that coyotes have been spotted in and around the Fells.
  • Finally, I feel the need to reiterate that trails directly abutting and crossing the Winchester Reservoirs are off-limits to hikers, runners, and bikers and should be avoided—even though signage to this effect is unclear and those trails appear wide, well-groomed, and inviting.

Does the Middlesex Fells offer the region’s most mind-blowing trail running? Of course not. But Bostonians are truly fortunate to have many miles of really solid trails basically in the shadow of the John Hancock Tower. And being able to scamper along those trails with two really solid fellow dads, week-in and week-out? Well, for me, that’s the real fortune.


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Steve Holt

Steve Holt is the associate editor of AMC Outdoors and edits AMC's Running Wild blog.