Middlesex Fells Skyline Trail

Feb 12, 2024 | Hikes and other fun

The Middlesex Fells is a reservation area that spans a large space in Medford and Winchester that surrounds the reservoir. We started at a trailhead on the Medford side near the tower.

Although we had intended to do the Skyline Trail for the whole distance – the trail markings are spotty in places, and ended up starting on the Quarry Road, picking up the actual Skyline trail at one of the later crossings. (That is one of the nice things about this trail system — all of the trails cross other trails — which means that, if you get on the wrong path, you can usually rejoin your original trail further down.)

The trails are technically all supposed to be on-leash (based on the signage) but nearly every dog we met was off-leash, so we went off-leash as well.

The Skyline Trail portion lives up to its name. If there is a hillside (up or down) the skyline trail takes that path. There is ALOT of climbing – although nothing vertical. From the path you can see on the map, we only matched the actual skyline trail about 2/3 of the hike — and we had 856 feet of elevation change which my fitbit counted as the equivalent to over 300 flights of stairs.

About one third of the way around the loop from where we started is Sheepsfold Dog Park. Although calling it a dog park is a little misleading, since it’s actually just a wide open field. There is no fencing – so, if your dog has poor recall, this is not a place that I would recommend. Honestly, Maizey was more interested in getting back on the trail than in playing in the field.

The path does parallel the street in very close proximity in some sections, and passes very close to Rt 93 as well – so please be careful if your dogs are off-leash.

Many sections of this reservation are used by mountain bikers, so be prepared to step off to the side and control your pup when you see/hear them coming up or down the trail toward you.

In all, this trail kicked our butts. Both me and the dog were tired after 8.5 miles of hiking, especially given the climbing that was involved, although we may go back in the summer to see what the place looks like in full bloom.

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