Explore the most popular dogs on leash 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.

hiking
2 days ago

Not too far from the city, great views of the skyline. Not too crowded, even on a gorgeous not-too-hot July Saturday. Ended up getting lost near Bear Hill but was able to find the trail again (it was a little annoying having to pull out the map/phone).

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!

trail running
8 days ago

great trail! there is everything I like. you have rocks, roots, singletrack, wider paths, great view from Wrights Tower. marked well. I didn't miss any mark during my first run there.

hiking
11 days ago

Enjoyed the diversity in elevation gain and descends. Agree that it is isolated however there are parts of the trail that intersect with others where we found ourselves yielding to cyclists. It was not too rocky. With a few tiny detours the hike ended up over 8 miles. Signage is sparse about two thirds of you hike counter clockwise. Hiked with a 21 lb backpack to train and hiked the trail in a little over 4 hours. Started on the trail at 5:40am to avoid the heat on the 4th of July and found myself faced with lots of relentless mosquitos despite repeated big spray application on my neck and hat. Long sleeves suggested. Despite bugs and some small lost moments, I really enjoyed the trail and feeling surrounded by forest. No real views but quiet and totally zen. Would hike it again!

hiking
14 days ago

So here’s the deal on the skyline loop trail (as of 6/2018): It’s a fun trail, nice that it’s so close to the city and the suburbs, but is mostly isolated. That being said, there are significant portions on the trail where the signage is either unclear or non-existent, which makes for an unpleasant experience, we had to pull out my phone to check the map and ensure we were still on course multiple times - I’d rather not be on my smartphone all the time on a hike. The trail markings are also inconsistent, with markings on trees and the ground regardless of whether you’re above the tree line or not. As a rule I think markings should be on trees below the tree line and on the ground above the tree line. Now only about 20-30% of the trail is like this, so for the most part it was fine. Overall, a nice trail but nothing memorable.

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

trail running
1 month ago

I run at the Fells frequently and Skyline is a good trail. Not marked that well in some spots as you get to the southern end of it. Definitely keep your pace expectations in check. Very technical in some spots so it leans on the more difficult side of "moderate" if you are running it for time. Probably the best trail in the Fells for a challenging hike.

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.

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
1 month ago

The classic here, nothing amazing but still worth doing if you can't get out of the city. The tower overlooking the city south, or up north, are the highlights

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!!

I’m new to backpacking and I am in training for bigger ,longer hikes. This trail is serving me well. It has many ascents and descents as well as ledge. Well marked . It is taking me between 4-41/2 hours depending on size of my pack.

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.

hiking
3 months ago

Lots of variety. Beautiful trail without too much traffic on a Saturday.

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.

Great train, light traffic, can be done in parts, if you tire out just take a fire road close to it.

trail running
9 months ago

Great and local. Wish I knew about it when I was younger.

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

Great trail! Very well marked.

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