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The recommended outer loop hike at Rocky Woods with rewarding viewpoints and access to Chickering and Echo Ponds.

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423' 129 m


227' 69 m


408' 124 m


407' 124 m



Avg Grade (2°)


Max Grade (12°)

Dogs Leashed

Features Fall Colors · Fishing · Lake · Views

Free for Trustees members. $5 parking fee for non-members. Open daily from sunrise to sunset, all year.


This loop hike is a dependable option for visitors looking for a nice outing or hoping to visit a good amount of the reservation, as it tours many of the outer trails. Given the number of trails that cross from one side of the loop to the other, you can also shorten your hike by skipping the lollipop section out to Cedar Hill and bypassing the outer loop by crossing on the Quarry Trail, Hardwood Notch Trail, or Ridge Trail section near Mine Hill.

The majority of the trails at Rocky Woods are wide and well maintained without too many major obstacles to look out for. Given the number of wetlands in the area, you'll also find a footbridge around Echo Pond and numerous opportunities to spot wildlife that live or congregate around the ponds. These four man-made ponds are also open to catch-and-release fishing.

Need to Know

Restrooms, picnic areas, accessible fishing platforms. Open to bow hunting in sections of the reservation. Between the 18th and 19th centuries, Rocky Woods was logged and accessed for granite quarries. By the 1920s, the land was no longer being used and was bought out by Dr. Joel Goldthwait for the purpose of developing paths, which he then donated in 1942, spurring numerous land donations that helped establish the reservation.


The trails at Rocky Woods can be traveled in any direction. This loop begins at the main parking area off Hartford Street and heads north toward the Chickering Pond Trail. Here, you'll find the Visitor's Center and restrooms. Turn right at the pond (east) to continue on the Chickering Pond Trail, passing the Noanet Trail on the right. At the next intersection (4), turn right for the short and sweet climb to the Cedar Hill Overlook and its rewarding viewpoint.

Retrace your steps back to intersection 4 and turn right (west) to continue in the counterclockwise direction of this loop. After a hundred feet or so, turn right onto the Ridge Trail. This trail is part of the yellow-blazed loop, which is made up of multiple trails. Begin this climb with the option to explore a short spur on the left for another viewpoint.

Continue heading southwest on the yellow-blazed section of the Ridge Trail, until you arrive at intersection 7. Here, turn right toward intersection 8, as you head toward the western boundary of the reservation on the Wilson Swamp Trail (staying to the right at intersection 8). This section is blazed in blue.

The Wilson Swamp Trail bends to the southwest along the border of the reservation with a nice, flat grade. At intersection 10, turn left to continue onto Cheney Pond Trail, which is also part of the blue-blazed loop. At intersection 13, you have the opportunity to turn left onto the blue-blazed section of the Ridge Trail toward June Pond. However, this loop hike continues south to intersection 14 where it begins the return stretch eastward on the East and West Trail and Echo Pond Trail. Back at intersection 1, turn right to return to the gatehouse and main parking area.

Flora & Fauna

Turtles, frogs, songbirds, deer, fish.

History & Background

A notable area for being split between the Charles River watershed and the Neponset River watershed.


Shared By:

Zander Göpfert

Trail Ratings

  3.5 from 2 votes


  3.5 from 2 votes
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in Massachusetts


19 Views Last Month
1,710 Since Oct 23, 2019
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Floating bridge that is part of the yellow blaze connector over Echo Pond.
Jul 7, 2018 near Medfield, MA
View from Cedar Hill
Jul 7, 2018 near Dover, MA
Echo Pond looking south. The trail runs right along the bank, or to the left of the large rock when the bank is too wet.
Jul 7, 2018 near Medfield, MA



Current Trail Conditions

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Mar 18, 2023
Shea Mizuno
did some minor offshoots to check out vistas and boulders 4.5mi — 1h 45m

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