Looking for a great trail near Winchester, Massachusetts? AllTrails has 6 great hiking trails, dogs leash trails, forest trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails in Boston Harbor Islands State Park, we've got you covered. You'll also find some great local park options, like Lake Skinner Recreation Area or Mcdonald Field. Just looking to take a quick stroll? We've got 4 easy trails in Winchester ranging from 1.3 to 3.8 miles and from 173 to 269 feet above sea level. Start checking them out and you'll be out on the trail in no time!


nature trips

dogs on leash



kid friendly



Winchester, Massachusetts Map

beautiful hike with clear paths

1 month ago

A great family trail. Not much to see other than the long pond but a nice walk nonetheless. Dogs are not allowed in the large reservoirs but it seems they are allowed in long pond. The trail is heavily shaded and you might encounter some bugs in the summer.

Good I bring the dogs off leash no swimming tho I hear

Decent trail, very clear path, more of a walk through the woods than a hike. Small black bugs, not many mosquitos (thank goodness, EEE!) Few views of the reservoir. 2.5 miles, took about an hour with very few short stops.

A nice hike to do with kids with some great water views and lots of places to explore.

beautiful place

Good 2 mile loop for probably a run but would say it’s more on the easier side.

I took another hike in spring and love it. The landscape is so green and luscious it is an absolutely rejuvenating sight. It's a just a little over two miles so it's a good workout after work but I wouldn't go out in my work shoe again. I hug the pond's shoreline more this time and there's quite a bit of uphill and downhill so I would definitely wear sneakers at least. It was a little muggy day so I regretted not bringing a bottle of water as well. Towards the end of the loop I really could use the bottle of water I left in the car.

6 months ago

poison ivy everywhere off trail

Beautiful scenery. Not to difficult.

7 months ago

Trails are well-maintained and there are some spots where you can take in good views without running into foot traffic. It’s just over 2 miles and not overly crowded, so ideal for the casual walker and dog owner. It’s also a popular spot for mountain bikers. If you’re a competitive runner looking to run hard and fast, this area could be frustrating because people will get in your way as will dogs (many are off the leash). It was a relaxed run for me, so solid 4/5.

Great property, wish I was closer. Will be back!

I took another hike in mid fall hoping to catch some more nice late fall foliage and was not dissapointed. It's an easy walk but rewarding esp in a warm sunny November day and with all the colors of fall still around. I like how pretty these berry trees along the path, I don't know the name but they're quite picturesque.

Very beautiful reservoir! Lots of different trail options so you can really personalize how you want to hike. The only reason this isn’t 5 stars is that parking was tricky, some trails didn’t have the best markings and a big part of it was supposed to be off limits but it was really unclear where and those areas seemed to be just as crowded as everywhere else. But I absolutely want to go back and do more exploring, it was a truly beautiful area!

Not really hiking. A nice walk around the lake.

Nice, peaceful hike. Not strenuous but the mileage makes it a good hike.

Mon Aug 20 2018

I've hiked this trail several times. It is a short and easy hike to do but other than Long Pond, there isn't much to see. Last time I hike it was in fall for fall foliage so it was one of my more interesting hike.

One of the best hiking trail in the Boston area. The views is absolutely incredible and the sunset is wonderful too. This trail is relatively short so I usually combine it with other trail. I also seldom complete this trail without a detour up Bear Hill as well. I enjoy the climb and the view from Bear Hill tower. And other times, I combine it with the trail that goes through the Middle and South Reservoir as well.

Sun Apr 01 2018

Fairly easy trail, conveniently located. Long Pond is nice, but there aren’t many other interesting features.

Sun Jan 28 2018

Parking lot at (42.4496220,-71.1257951). Nice, short walk.

Sun Nov 12 2017

Principally a pine forest on shallow soil over glacial stoney rubble. Mostly ~50 year old tree. Just few older. The trail rounds the small shallow lake mostly above. Petty views of that water. At the highest point a short detour to the west reveals an excellent vista. Pine forests, in my opinion, are a bit dull. The Fells are popular, this trail is less crowded than others.

5 days ago

24 days ago

26 days ago

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