Explore the most popular walking trails near Medford with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

A great day hike! parked at Upper Sheepfold. prepare for a good 3 to 3.5 hour hike.

4 or 5 great spots with views of Melrose and Malden and even as far as Boston and Revere beach. Definitely a tough loop, very rocky and a lot of up and down. We took our time to a degree and total time was around 4 and a half hours. Managed to spot a deer and two owls also! Great trail overall and not too crowded mid afternoon

great trail!

Some trails could be better marked, but overall very good.

Sound autumn view

A good easy hike when you don't have much time. The view over Spot Pond is simply breathtaking.

I really enjoyed this trail. It’s difficult enough to be a challenge with some light rock climbing (nothing crazy) and steep hikes, but still moderate enough to be a nice leisure hike as well. Plenty of nice look out spots by the tower and the lake was a nice treat. There’s tons of trails connecting as well so it’s super easy to customize your hike if you don’t want to do the full course of one specific trail. Would totally hike it again.

The west side is nicer

hiking
1 month ago

The two towers are the highlights but it's still worth getting lost trying to go around the lake (skyline)

hiking
2 months ago

Came here for a quick hike and some Yoga. Not the best slice of nature because you're so close to the road. You can here all the cars, but great wildlife. Saw a snake and some beautiful birds!

Nice trail near the city, great views of Boston at Wright’s Tower, good rock scrambling. You’ll see lots of people on a nice day.

Did this by accident because the rock circuit is poorly marked. Decent run.

By far my favorite place to go on my days off. I actually really enjoy how busy it can get - I do a full loop each time and cross over between several trails. On a weekend, I'd run into someone else maybe every 20 minutes... But by far my favorite trail to do from start to finish is the skyline trail. I would rate the skyline trail as moderate, but everything else is easy. It's very dog friendly. We always start at Sheepfold and go from there. Once you know the trails, it's easy to cut through - they're decently marked. I'm a relatively fit person but I like to take slow hikes with my dogs - the full loop and a little more takes us about 1.5 hours. I love it!!

hiking
3 months ago

Not too hard, good views of Boston from ledges, there is a stone tower that is occasionally open, which provides views of the Fells and other nearby landmarks.

This trail was a fun walk. The difficulty was easy to moderate at most. We found the trail markings to be insufficient, especially at some intersections. Surprisingly long given the location. Will likely hike it again in a different season.

I’ve gone snowshoeing along this route, there are multiple solid rock climbing spots. The west side of the Fells is too crowded but this side is awesome

Great winter walk close to the city. Helps scratch the hiking itch.

This is my 4th time here, very nice place with different views. Rocky and lake .
It took me 6 hrs slow- medium walk. Fresh air .
1,5 liter of water .
Not too hard really, any fit person can do it. And what is nice here if you get tired from one trail you easily can switch to an easy one like the blue trail.
Enjoy and stay fit and healthy this is the ultimate wealth.

Really hee re

Beautiful, a few climbs under the trees and rocks. pretty view on the Winchester reservoir. plan to return in the fall. the app was very useful.

Awesome little hike - some challenging scrum and bouldering but nothing too nuts

Really nice trails with lots of options! Made our way to Spot Lake which was gorgeous.

Hiked this today- great hike with some parts being more access-road-like and others being wooded trails. Part of the trail is the Rock Circuit trail which can be lots of rock climbing up/down which was difficult for a beginner like me, but a good challenge.

hiking
Sunday, July 09, 2017

Great hike. Brought my dog and let her off leash for parts of the trail. Nobody seemed to care.

hiking
Tuesday, July 04, 2017

Nice trails but not very easily marked. The app was helpful for seeing where the various paths connected.

hiking
Saturday, June 24, 2017

Poor signage on the trails. Easy to get lost

Saturday, June 03, 2017

Good trail but easy to get lost. I stuck with the white trail markers which lead to the tower. Easy enough to do with dogs.

One great view of Boston after a quick rock scramble. Otherwise the hike was wooded with a few small ponds. I skipped several sections of the trail due to time constraints and lack of interest in climbing all the little rocks. I also skipped the beginning/end because I parked at the ice rink parking lot. Difficult to follow the mapped out loop because the blazes change and many offshoots aren't clearly marked. Could hear road noise for over half the hike. Took me about 2 hours.

hiking
Saturday, May 20, 2017

The parking lot fills up pretty quickly on weekends, so arrive early. Trail can be tough to follow in some spots with so many trails intersecting, so grab a map at the trailhead. Great hike considering how close it is to the city.

hiking
Tuesday, May 16, 2017

Nice enough hike given how close it is to the city. Rocky and with enough small hills to be a good little workout and prep for hiking in points north.

Load More