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Routes
Running trails & routes
United States
Massachusetts
Norfolk County

Rocky Woods loop

Moderate

3.4

(5)

50

runners

Rocky Woods loop

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:

Rocky Woods Reservation

Waypoints

A

Start point

Parking

Get Directions

1

632 m

Chickering Pond Trail

Highlight (Segment) • Trail

The Chickering Pond Trail is central to the Rocky Woods Park trail system. It provides access to several other trails, including the Noanet Trail, Tower Trail, Quarry Trail, Ridge Trail, …

Tip by

2

1.32 km

Cedar Hill overlook

Highlight • Viewpoint

A little south from the actual Cedar Hill peak is this small trail that leads to a rocky outcrop where you can enjoy expansive views across the Rocky Woods Reservation and surrounding area.

Tip by

3

2.33 km

Rocky Woods Reservation

Highlight • Forest

The Rocky Woods Reservation in Medfield, Massachusetts, covers nearly 500 acres and has miles of rocky and wooded hiking trails. The property is pretty hilly and offers some higher elevation …

Tip by

B

5.78 km

End point

Parking

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

Powered by Foreca

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.

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Frequently Asked Questions

Where can I park for the Rocky Woods loop, and are there any fees?

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.

Is the Rocky Woods loop dog-friendly?

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.

What is the best time of year to jog the Rocky Woods loop?

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.

Are there any permits or entrance fees for Rocky Woods Reservation?

There are no specific permits required for jogging the trails. However, there is a parking fee for non-members of the Trustees of Reservations.

What is the terrain like on the Rocky Woods loop?

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.

What scenic points or landmarks will I see on the Rocky Woods loop?

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.

How difficult is the Rocky Woods loop for jogging?

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.

What kind of wildlife might I encounter?

The wetlands and forests of Rocky Woods Reservation attract diverse wildlife. You might spot various songbirds, beavers, and turtles, especially around the ponds.

Does the Rocky Woods loop connect with other trails?

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.

Can I customize the length of my jog on the Rocky Woods loop?

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.

What should I wear or bring for jogging this loop?

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.

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