Cross Fells Trail: Trailheads, Route and What to Expect

The Cross Fells Trail is a 4.7-mile, blue-blazed trail that crosses Middlesex Fells Reservation from the western Fells near Medford High School to the eastern Fells. DCR rates it difficult and estimates about 5 hours one way.

It's the only blazed trail that links the two halves of the Fells. That means it's one way, not a loop, so plan your ride back before you start.

Cross Fells Trailheads

West start: Gate 1 on Winthrop Street in Medford, near Medford High School. The blue blazes begin as soon as you enter the gate.

East end: Gate 58 at the top of Goodyear Avenue, a short, steep street off Washington Street. Oak Grove station on the Orange Line is a few blocks away.

Middle access: the trail crosses Woodland Road near Flynn Rink. DCR's free lot there, at 300 Elm Street in Medford, is the easiest place to park if you want to hike just one half of the trail. See our parking guide for other lots.

The Route, West to East

DCR describes the trail as a good sample of the whole park. In order, here's what you pass:

1. Wetlands along Whitmore Brook in the western Fells.
2. A crossing of South Border Road.
3. Wenepoykin Hill, where Friends of the Fells points out a view of the Boston skyline.
4. A short road walk on Route 28, passing under the I-93 overpass, then back into the woods at Gate 28.
5. Quarter Mile Pond, the open water DCR mentions in the eastern Fells.
6. A crossing of Woodland Road near Flynn Rink, back in at Gate 33.
7. A view of Hemlock Pool, then a crossing of Fellsway East.
8. The end at Gate 58 on Goodyear Avenue.

Road Crossings to Watch

DCR asks hikers to use caution at four crossings: South Border Road, Route 28, Woodland Road and Fellsway East. At Route 28, the Friends guide crosses to the sidewalk on the far side and walks under the I-93 overpass to Gate 28.

Good For / Maybe Skip If

Good for: fit hikers who want a long day, and anyone who wants to see both sides of the Fells in one trip.

Maybe skip if: you have small kids, a stroller or a tight schedule. DCR rates it difficult, many single-track sections in the Fells are steep, rough and rocky, and the full trail takes most of a day.

Doing It One Way, by Car or by T

Two cars: leave one near the east end and drive to Winthrop Street to start. That way you hike the whole trail once.

By T: Friends of the Fells published a full guide that starts in West Medford, walks to Gate 1, hikes the whole trail east, and ends at Oak Grove station for the Orange Line home. More options are on our public transit page.

Half the trail: park at Flynn Rink and hike out and back in one direction. East toward Gate 58 is the shorter half.

Dogs and Rules

• The reservation is open dawn to dusk. Start early so you finish in daylight.
• Dogs must be on a leash, with up to four dogs per person. The only off-leash area is the Sheepfold field.
• Stay on the blazed trail. DCR is closing the many user-made side paths.
• Avoid the trail after heavy rain. Walk through puddles, not around them.

Carry a map. The official DCR trail map shows the full Cross Fells route, and our trail map page explains how to read it.