Summary

If you are new to winter hiking [while being able to sleep in and rely on public transportation], this hike is for you! This is a moderate loop on the Skyline Trail that is surprisingly rugged for a trail so close to the city that provides a wonderful 6-hour workout in Medford, MA!

Don’t let this trail’s relative elevation gain [just around 1,540’] and proximity to a major city fool you: this 8-mile circuit is no easy walk in the park.  Fortunately, however, we are rewarded with excellent views at several points—of downtown Boston to the south, Atlantic Ocean to the east, and Mount Wachusett the northeast and on a good day, Mount Monadnock! The Skyline Trail will take us to notable locations such as Panther Cave, Wright’s Tower, and an old soapbox derby track.

The majority of the white-blazed path is wooded, with the west portion of the trail being more coniferous and the east boasting more deciduous trees. We will pass fields, vernal pools, wetlands, rocky outcrops, and ponds along with climbing several hills, some of which have rather steep ascents, that offer views of the Boston skyline and surrounding communities.   We will be hiking at a very slow pace since I’m recovering from a knee replacement surgery so we’ll have plenty of time to enjoy the scenery.  

We meet at 10AM at the Bellevue Pond parking lot. If using public transportation, to get to the west side take the MBTA Orange Line to Wellington Station and #100 bus to Fellsway W @ Ridgeway Rd. The Bellevue Pond entrance is a short walk up South Border Rd.

This is a good opportunity to practice layering, carrying (slightly) heavier packs, and other winter hiking skills! Have you ever survived a cold day in Boston? Have you ever successfully walked around in the woods before? If you answered yes to all two questions, then this trip is for you! If you have any concerns, feel free to contact me.

If you want to try new gear, techniques, skills, or equipment, a trip like this is the perfect time! Don't show up with a 100% cotton outfit you've been dying to try out in the snow. Bring hiking boots [winter/insulated recommended] and Microspikes. We may need snowshoes if we had a recent snowstorm so we’ll keep you posted. Please have the appropriate gear/clothing to hike this time of year and the appropriate number of layers to keep your core body warm. We recommend hand warmers for your gloves. Be sure to carry water, snacks and lunch.  

Food and drink afterwards Pearl Street Station Restaurant with a bustling bar area, and a quieter set of rooms in the back for dining. The steak tips, wings, pizza, calzones and Italian sausage are all excellent. Address is 53 Summer Street, Malden MA.  

Directions To Trailhead Parking Lot

The hike begins at the parking lot adjacent to Bellevue Pond in the southeast corner of the wester section. We will meet at 10AM at the bulletin board. We are driving a blue Toyota Tacoma.

Is easy to reach from exit 33 of I-93 [watch for signs for Route 28, Fellsway West and Winchester]. The exit leads to a traffic circle on South Border Road for 0.2 mile to the parking area on the right.

If using public transportation, to get to the west side take the MBTA Orange Line to Wellington Station and #100 bus to Fellsway W @ Ridgeway Rd. The Bellevue Pond entrance is a short walk up South Border Rd.