Local Hikes in the Middlesex Fells

“Hiking is a lot like life: The journey only requires you to put one foot in front of the other … again and again and again. And if you allow yourself opportunity to be present throughout the entirety of the trek, you will witness beauty every step of the way, not just at the summit” -Unknown

As we all sit in our houses waiting and wondering if the world will ever go back to some sort of normal, there is no better time to hit the local trails and see what is sitting in your own backyard. So here I am to be your guide to what trails are the best to hit in these uncertain times.

First things first go download the AllTrails app on your phone and see what your local area has to offer!

Skyline Trail Loop – 7.6 Miles | I have never completed this trail in full I have down all different parts of it, however I highly recommend this trail (I plan on completing it in full in the next few weeks). There is very minimal elevation gain as there is throughout The Fells. It offers you a chance to really see The Fells for all of its beauty, you will pass all 3 reservoirs that sit on this side of the reservation and get. dome great fews of Boston from multiple locations.
Pine Hill – 0.9 Miles| This is if you are looking for a short easy hike that will lead you to a complete view of Boston, this trail leads you up to one of the towers that sits in the reservation – Wright’s Tower. The tower is usually open spring thru fall and you are able to climb to the top and get even better views. I grew up going to this tower A LOT. It is a very busy trail and parking usually fills up quickly but if you get there early enough to beat the crowds its a great morning hike.
Two Towers Hike – 6.1 Miles | This hike is super fun and leads you to not only only Wright’s tower but also Bear Hill Tower. Something to keep in mind about this trail is that you are walking next to the highway most of the time which can make it unenjoyable for some people. When I did it I started at Bellevue Pond (South Border Road) and headed through Sheepfold to the second tower; but you could do it either way.
Southern Middlesex Fells Loop – 3.4 Miles | This trail is mostly flat land but is usually extremely peaceful when not busy with crowds. You pass the southern side of the south reservoir and can walk out to the little water hut or sit on the rocks and just take in the view.
South Reservoir Loop – 2.7 Miles | This trail is super easy and family friendly, however heavily trafficked pretty much year round.

6. Rock Circuit – 4.2 Miles | I did this one last Saturday – I headed out early and parked at Flynn Rink to try and beat the big crowds. It was a nice steady hike with some views of Boston from certain rock tops, a few light scrambles here and there but over all a beautiful hike. The only downside is you need to cross a portion of the Fellsway to complete of the loop, once looped back around I went off trail a bit here and there to explore other sections.

7. Bear Hill Loop – 1.9 Miles | This trail leads you straight to the “second tower” aka Bear Hill Tower. I grew up calling this the second tower because I lived near Wright’s Tower and it has just sort of stuck like this forever. This trail is mostly in Sheepfold and you will definitely want to head off trail to see views of the North Reservoir!

8. Cross Fells Trail and Half Mile Road – 1.3 Miles | The is the trail that leads to Turtle Rock and if you grew up in Medford or surrounding cities you know this was the “secret” swimming spot everyone went to. It is a super easy trail and can offer pretty views of Spot Pond.

9. West Middlesex Fells Reservation Bike Loop – 6.5 Miles | This trail takes you around the western side of the Fells and is pretty flat making it an easy walk. On these longer trails it is always nice to pack lunch and eat when you come across a spot with a great view of the water.