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INTRO TO WINTER HIKING AT MIDDLESEX FELLS SKYLINE LOOP TRAIL

The day couldn’t have been more perfect for an outdoor adventure in the winter wilderness!

Saturday, February 8, 2025
Medford, MA
Moderate
Hosted by Gandalf

The trip report

Written by Gandalf

Date: Saturday, February 9th

Weather: Mostly sunny, temperatures in the 30’s with no wind

Trail Conditions: Frozen granular with ice hidden beneath the snow

Overview:

The day couldn’t have been more perfect for an outdoor adventure in the winter wilderness! With good friends, clear skies, and spectacular winter scenery, the 8-mile Skyline Trail hike through Middlesex Fells was a highlight of the season. The trail, with its blend of woods, wetlands, and rocky outcrops, offered both physical challenge and incredible views of the Boston skyline.

Trail Experience:

The Skyline Trail features an ever-changing landscape as it winds through wooded areas, ponds, and hills. The western part of the trail is mostly coniferous, while the eastern half boasts more deciduous trees, offering a mix of environments to explore. Along the way, we passed through fields, vernal pools, and rocky outcrops that provided stunning vistas of the Boston area and surrounding communities.

Start of the Hike:

Our adventure began at Bellevue Pond at 10 AM, but finding a parking spot proved to be a challenge. We made the most of the wait for other to arrive by watching several handsome men with their dogs, excited for the conditions ahead. The sun made the cold day feel crisp and refreshing, perfect for hiking, though the trails were a bit icy, covered in frozen granular snow with a few bare spots.

Key Stops & Highlights:

Wright’s Tower: We started by stopping at Wright’s Tower, where we admired the views from the old fire watch tower and the urban landscape below. From the outcrop past the tower, we had a sweeping view of Medford and Interstate 93.

Sheepfold Area: As we hiked on, we passed Sheepfold, where a number of dog owners were out enjoying the trail with their furry companions. The area around the old soapbox derby track resembled a ski hill, adding a playful vibe to our hike.

Lunch Break: Our group decided to skip Bear Hill Tower for lunch (thanks to Alexander’s suggestion, as there wasn’t much of a view there) and instead enjoyed a peaceful rest under towering Eastern White Pines. During lunch, we were joined by a Cooper’s Hawk, which Jim expertly identified. Watching this magnificent bird up close was a special moment on the trail.

North Reservoir: We continued our journey around the North Reservoir, where we climbed up the dam for a beautiful view. The snow-covered reservoir created a stunning and peaceful sight, a true work of art crafted by nature itself.

Western Trail Section: The western edge of the reservation was a quieter and more tranquil section of the trail, with tall pines creating a serene atmosphere. We also spotted a deer in this section, which was quite a sight, especially given the proximity to residential areas.

The Final Leg & Fat Tire Bikers:

By the time we reached the final stretch of the trail, fatigue was starting to set in. We were all eager to return to the car, but the peacefulness of the section helped make it a calm and serene finish. Fewer hikers were around, though we did cross paths with a few riders on fat tire bikes, enjoying the flatter terrain of the western end.

End of the Hike:

We completed the hike around 4 PM, all feeling satisfied with the day’s adventure. Afterward, four of us headed to Pearl Street Station for a well-deserved hearty meal, reflecting on the beauty and challenge of the hike.

Conclusion:

Another successful trip to the Middlesex Fells! The Skyline Trail never disappoints, offering a perfect mix of natural beauty, physical challenge, and camaraderie. Looking forward to the next adventure with the GayOutdoors group!

Event photos (24)

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About this event

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.  

Who came along (8)

Gandalf SUSTAINING
Gandalf
Thornton, NH
jcmulloy GUEST MEMBER
jcmulloy
Cambridge, MA
Rob Bonney SUSTAINING
Rob Bonney
Cambridge, MA
A member
Profile hidden
Michael GUEST MEMBER
Michael
WOBURN, MA
HikerBiker SUSTAINING
HikerBiker
Manchester, NH
Robert GUEST MEMBER
Robert
Medford, MA
DavidElston GUEST MEMBER
DavidElston
Merrimack , NH

Comments

A member · Feb 7, 2025
See everyone at the parking lot. Looks like we take exit 24 (formerly exit 33)?
A member · Feb 8, 2025
See everyone at the parking lot. Looks like we take exit 24 (formerly exit 33)?
A member · Feb 8, 2025
See everyone at the parking lot. Looks like we take exit 24 (formerly exit 33)?

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