Jamaica Pond

Brookline, Massachusetts

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3 Reviews
4 out of 5
An easy recreational trail offers a popular and pleasant circuit around historic Jamaica Pond.
AMC's Best Day Hikes Near Boston


AMC's Best Day Hikes Near Boston

by Michael Tougias (Appalachian Mountain Club Books)

An easy recreational trail offers a popular and pleasant circuit around historic Jamaica Pond.

©  Michael Tougias/Appalachian Mountain Club Books. All Rights Reserved.

Activity Type: Hiking
Nearby City: Brookline
Distance: 1.5
Trail Type: Loop/Lollipop
Skill Level: Easy
Duration: 45 minutes
Season: Year-round
Local Maps: USGS Boston South
Driving Directions: Directions to Jamaica Pond

Recent Trail Reviews


This is a great trail for some aggressive hiking and great views. It never gets old overlooking Boston and the bay. Middlesex Fells Rock Circuit is a moderate to hard 4 mile hike that includes an array of ascends and descends. This is part of the greater Middlesex Fells Reservation The trail runs through the east side of the reservation and its pinnacle (aptly named Pinnacle Rock) overlooks Oak Grove, and in the distance a great view of Boston. The trail start out on Woodland Road and the best place to park in in the ice rink on Woodland Road. Alternatively there is parking about 100 yards up from the rink on the same side of the road. The entrance to the trail looks like a utility path blocked by a large metal beam. Just go around this and you’ll see the entrance sign (Photo on left). From here you follow the blue marked trail up the hill for about a 1/4 mile until you see the split in the trail for the white trail (Rock Circuit Trail). You can read more of my new england trail reviews http://www.moderndaythoreau.com


I have enjoyed this trail numerous times. The views of Boston are incredible. It's hard to believe you can take a hike this difficult so close to the city. It's a workout. Wear your Ipod to drown out the occasional area where you hear traffic or planes heading in/out Logan and you'd think you were in NH or VT. Parking is best (but limited) on the Lynn Fells Parkway. Avoid weekends if possible. A trail map is a must because so many go off trail making it hard to follow.


This trail was very accessible to the Boston Area, but parking was difficult to find. It may have been b/c of the recent snow on the ground, that the gates were closed. The trail map that I got from trails.com was not accurate, however. The trail signs on the trees did not match the map trail, which made for a confusing hike! However, I did like this hike and I highly recommend it to anyone, if they had an accurate map!

Trail Photos

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Apr 2018