Hike Southern Middlesex Fells Loop

Medford, Massachusetts

based on 9 reviews



3.5 miles

Elevation Gain

756 ft

Route Type



Added by Danielle Tourigny

This beautiful wooded loop trail in Middlesex Fells features a pond and a cave!

Park in the parking area near Bellevue Pond. There are multiple entrances to the reservation (some closer to the reservoir itself than others). I have spent days in there hiking around and never seeing the water and there are days when I just hiked right in to the water and sat and enjoyed it. The trails are perfect for mountain biking as well. I spent so much time here when I lived in Boston because it felt like you had completely escaped the city. You can hike around several miles and never see another person in the cooler months. You can find a quiet spot by the water that is completely your own. And since the reservoir is man made, the water is completely clear and still. It feels like a pristine lake. Middlesex Fells is definitely one of my favorite places. 

See trail map here for Southern Loop. If you want to do this one in the winter, bring your snowshoes!

Read More

Download the Outbound mobile app

Find adventures and camping on the go, share photos, use GPX tracks, and download maps for offline use.

Get the app


Dog Friendly
Family Friendly

Hike Southern Middlesex Fells Loop Reviews

Having grown up in rural wilderness, my husband and I love escaping the city to wander through these trails. On the weekends it’s less than a 15 minute drive!

Great park, I personally preferred the western part of the reserve. Three large water reservoirs and gorgeous scenery. One point: avoid the blue trail, a bit desert and gloomy

Nice spot to easily get out of the city. Mostly easy terrain but one or two more strenuous options with a few good views

Easy and fun trail. Wonderful place very close by Boston.

I have spent hours upon hours exploring this area. Whether I am just sitting at the reservoir or hiking up to the watch tower that overlooks the city, this reservation has provided lots of great memories and some extremely well cared for trails.

Beautiful hiking area. I took the Skyline Trail, from where I parked my car off of South Border Road, to Wright's Tower (great views of Boston and the surrounding areas.) Then I continued on the Skyline trail until it came to a junction with the Cross Fells trail and East Dam Road. From there I took East Dam until I hit the multi-use Mountain Bike loop and veered left. Followed the Mountain bike loop until it came to a junction met the Cross Fells trail again. Followed the Cross Fells trail back to the road. I didn't end up at where I parked my car exactly, but it was only 500 ft up the road so no problem. This was my first time hiking at the fells and I can be kind of confusing at first, but as long as you follow the trail markers and know which way you want to turn when you switch trails (use a map) then you can make a number of different length loops. I hiked about 3.5 miles following this route.

Leave No Trace

Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!


Bike or Run on the Charles River Path

Freedom Trail

Run the Jamaica Pond and Victorian Jamaica Plain Loop

Run the Arnold Arboretum Trail

Hike around Walden Pond

Explore the Bunkers at Fort Revere