3.4
(5)
50
runners
00:44
5.78km
90m
Running
Jog the moderate 3.6-mile Rocky Woods loop through varied terrain, past ponds, and to the Cedar Hill overlook for scenic views.
Last updated: February 26, 2026
Tips
Your route passes through protected areas
Please check local regulations for:
Waypoints
Start point
Parking
Get Directions
632 m
Highlight (Segment) • Trail
Tip by
1.32 km
Highlight • Viewpoint
Tip by
2.33 km
Highlight • Forest
Tip by
5.78 km
End point
Parking
Way Types & Surfaces
Way Types
5.40 km
314 m
< 100 m
Surfaces
2.71 km
2.69 km
314 m
< 100 m
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Elevation
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Weather
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Today
Tuesday 26 May
29°C
11°C
0 %
Additional weather tips
Max wind speed: 14.0 km/h
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This route was planned by komoot.
Parking is available at the Rocky Woods Reservation. Please note that there is a fee for parking if you are not a member of the Trustees of Reservations.
Yes, the Rocky Woods Reservation is generally dog-friendly. However, always ensure your dog is kept on a leash and that you clean up after them to maintain the natural beauty for all visitors.
The Rocky Woods loop is accessible year-round from sunrise to sunset. Fall is particularly beautiful due to the vibrant foliage. Spring and summer offer lush greenery, while winter provides a peaceful, snow-covered landscape, though trail conditions may vary.
There are no specific permits required for jogging the trails. However, there is a parking fee for non-members of the Trustees of Reservations.
The terrain is varied and rugged, featuring a mix of wide, well-maintained paths, granite hills, knolls, boulders, and exposed ledges. You'll encounter small inclines and descents, and some sections may have roots. While parts are smooth, others require more attention due to the rocky nature.
You'll jog through pleasant woods and past several man-made ponds, including Chickering Pond, Echo Pond, June Pond, and Notch Pond. A significant highlight is the Cedar Hill overlook, which offers expansive views across the reservation. You'll also pass by the Chickering Pond Trail and through the Rocky Woods Reservation itself.
Komoot rates this specific Rocky Woods loop as moderate. While some sections are relatively smooth, the presence of hills, rocks, and roots means it requires good fitness and attention. It's a good choice if you're looking for a bit more challenge than a flat run.
The wetlands and forests of Rocky Woods Reservation attract diverse wildlife. You might spot various songbirds, beavers, and turtles, especially around the ponds.
Yes, the Rocky Woods Reservation has a comprehensive network of interconnected trails. This loop specifically passes through sections of the Ridge Trail, Wilson Swamp Trail, Harwood Notch Trail, Cheney Pond Trail, East West Trail, Quarry Trail, Bridle Trail, Hemlock Knoll Trail, Tower Trail, Loop Trail, Chickering Pond Trail, June Pond Trail, Echo Pond Trail, Noanet Trail, and Woodcliff Hills Trail.
Absolutely! The reservation offers a diverse trail network, allowing you to shorten or extend your run by utilizing the many interconnected trails. You can easily cut across interior trails to create a route that suits your desired length and difficulty.
Given the varied and sometimes rugged terrain, wear appropriate trail running shoes with good grip. Bringing water is always recommended, especially on warmer days. Depending on the season, consider layers for changing weather conditions.