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

Chestnut Hill, Massachusetts Map
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I love this trail, but it can get very busy. finding dogs off leash is common if that's a concern for you. the biggest problem are the Canada geese that damage the trail.

The western portion of the southern loop was overgrown. Otherwise great hike. My toddler loved it

Fairly flat walk around Chestnut Hill Reservoir with occasional views of nearby buildings.

Nice place for an easy/moderate hike. Not a very long trail, didn't see any trail markings. I think you could spend about 1-2 hours at most hiking in here. Don't forget you can get across the road to the Webster conservation area too. This felt a little larger and overall more enjoyable hike with a few more ups and downs. The Webster conservation entrance wasn't very marked at all except for a white board that said public was welcome to explore the area till dusk. Hope they mark this up better.

5 months ago

Great place to take a run or sit on the bench and read a book...

hiking
6 months ago

We hiked the trail in late March after a somewhat recent snow. The hike is a good escape from the Boston urban landscape with plenty of pines, small boardwalks, a kettle hole pond, and according to a kiosk, a peat bog. You will see housing, a recycling center, and encounter traffic noise, but despite all of these elements, it is still a worthy hike. We did have some trouble navigating the trail as outlined by the AllTrails app. At about 1.5 miles into our walk, we encountered signs that read "road closed" at our designated route. After walking around for a bit looking for an alternative route, the trail seemed to disappear (I'm sure the snow did not help). We just retraced our steps to complete an out-and-back. Despite our troubles, it was a nice walk in the woods and very much appreciated by our dogs.

on Lost Pond Trail

hiking
Monday, October 02, 2017

The Lost Pond Trail is fairly wooded but still clear. I liked the outing when I went, but when I tried to finish the loop highlighted in this app on two different occasions, the loop was cutoff from both directions. I am not sure what was the reason and I did not see any signs providing an explanation. I would have liked to finish the entire trail, but I still enjoyed spending time there.

rock climbing
Wednesday, August 09, 2017

Came here for climbing a few times. The main cliff is right by the entrance. It was easy to walk around to the top of the cliff to set ropes. There are a few good vertical cracks but other than that the climbing is very difficult. If you poke around you'll find "Hammond Eggs" which is a circle of boulders with a few technical routes, bring a pad for spotting. The overhang is usually chalked up.

rock climbing
Tuesday, June 06, 2017

Came here for rock climbing and ended up hiking a bit. The rock is great for climbing and the trails are well maintained. Cool park if you live nearby, but not necessarily a destination spot.

Thursday, April 06, 2017

me and my girls hiked around in the snow, climbed all over the huge boulders and had a great time

trail running
Sunday, February 05, 2017

Nice wide trail with great views

walking
Thursday, October 20, 2016

The colors were beautiful in the fall. It was an easy walk and run.

hiking
Thursday, August 18, 2016

Lots of roots on the trail bed but a nice loop with plenty of shade.

trail running
Sunday, April 17, 2016

Great flat trail, dog friendly, beautiful surroundings, accessible by public transportation through green lines B, C and D.

hiking
7 days ago

hiking
2 months ago

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3 months ago

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4 months ago

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5 months ago

hiking
10 months ago

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