Are you looking for a great hiking trail close to the city of Boston? If you haven’t previously visited the Middlesex Fells Reservation, now is the time to go. The reservation contains some of the best hiking trails in Massachusetts. We have already told you about the Rock Circuit Trail Loop and the Virginia Wood Trail. Both are easy trails that can be quickly completed. However, If you are looking for a hike that is more challenging, I suggest taking the longer Skyline Outer Reservation Loop trail.

The Skyline Outer Loop Trail is a 7.7-mile, moderate hike that takes a little over three hours to complete.
Alex Whale/AllTrails
The trail is one of the state's best hikes for experienced hikers because it is full of turns and ups and downs.
The trail loops across a variety of terrain as it passes through the western Fells.
Alex Whale/AllTrails
Be sure to bring a map or field guide with you as the trail can be a little tricky to navigate at certain junctions.
As you hike across forested paths and up over boulders, it is easy to forget that you are just a stone's throw from the city.
Deb Martinez/AllTrails
That is, until you reach a scenic overlook and gaze upon the gorgeous views.
As you make your way along the trail, there are some really cool things to see including this observation tower made from stone.
Alex Whale/AllTrails
Wright's Tower dates all the way back to 1937!
And it looks just as cool from the inside!
Adilson Paulino/AllTrails
You will also pass a cave along the way. This is a great place to stop and rest or to take a photo.
Anna Suojanen/AllTrails
The Skyline Outer Reservoir Loop is dog-friendly, as long as your pup is on a leash.

This trail can be challenging, so be sure to bring lots of water with you to stay hydrated. A handy water bottle to have while hiking is the L.L. Bean Insulated Bean Canteen Water Bottle.

More information on the Middlesex Fells Reservation hikes can be found at Mass.gov. Have you hiked the Skyline Outer Reservation Loop or any of the other trails at the Middlesex Fells Reservation? Please tell us which one you enjoyed the most. If you enjoyed hiking at the Fells, be sure to check out our list of some of the best hiking trails in Massachusetts for 2023.

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Middlesex Fells Reservation, 4 Woodland Rd, Stoneham, MA 02180, USA