Rocky Woods Trail Guide: 3-Mile Loop Hike in Medfield, MA
Peaceful woods, lakefront paths, water access, and off-leash trails make Rocky Woods Reservation a must-do hike in eastern Massachusetts!
Bruin taking a dip at Chickering Lake, one of 2 lakes on this loop.
Captain at the top of Cedar Hill lookout- Top of Cedar Hill.
This 3-mile Ridge and Cedar Hill Loop meanders through a beautifully maintained Trustees property in Medfield, MA, offering scenic views and water access to multiple lakes.
In this post, you'll find everything you need to know to have a fun and successful hike here, including turn-by-turn trail directions!
Living in Connecticut, I venture to MA often to take advantage of lots of beautiful hikes in the Berkshires and at other Trustees properties. But this one felt incredibly special and peaceful, and one I would want to return to!
Tucked away in the quiet town of Medfield, just 25 miles southwest of Boston, Rocky Woods Reservation is part of the Massachusetts Trustees of Reservations. It offers a laid-back adventure and an excellent hike with scenic views just outside of Boston.
There are over 6 miles of trails within the reservation’s 491 acres and this loop along the ridge trail shows you all this property has to offer. Many of the trails within this 3+ mile loop are off-leash, allowing pups to roam free—what a treat! That alone makes it a destination-worthy hike, but when you add in two lakes where the dogs can swim and the scenic view from Cedar Hill, it becomes a must-do.
- Well-marked trails!
- Signs show which trails are on leash or off leash
- Love being able to let the dogs off-leash!
The dogs will be grateful for the freedom to roam, splash around, and take in the views, as there are approved off-leash trails here.
🥾 Rocky Woods Loop Overview 🥾
🗺️LOCATION: MEDFIELD, MA
🥾LENGTH: 3.08 miles (loop)
⏱️TIME & MONEY: 1 hour 30 minutes; $6 parking fee for non-Trustees members
📈ELEVATION GAIN: 384 feet
💪🏼DIFFICULTY: Easy to moderate
🌲CONDITIONS: Year-round; pine paths, lakeside trails
🌟HIGHLIGHTS: Swimming for dogs, views, easy to navigate, shady
📍Find the trailhead: From I-95/Route 128, take exit 31B onto Route 109 West. After 5.7 miles, turn right onto Hartford Street. After 0.6 miles, the entrance and parking (100 cars) is on the left.
From the Route 27 and 109 intersection in Medfield, take Route 109 East and bear left onto Hartford Street. After 0.6 miles, the entrance and parking (100 cars) is on the left.
Land manager: The Trustees, 200 High Street, Boston, MA 02110; (617) 542-7696; [email protected]
thetrustees.org
🩷 WHY YOU’LL LOVE IT 💚
- Approved off-leash trails
- Diverse scenery—woods, water, and small overlook
- Well-marked, wide paths
🌲 Rocky Woods Loop Details 🌲
Park in the large lot off Hartford Street and pay the $6 fee at the self-serve kiosk (credit cards accepted), unless you’re a Trustees member, in which case parking is free. From there, the trail loops clockwise.
After 0.3 miles, at Echo Lake, the path is a bit rocky as it hugs the shoreline. If you had a long car ride, now’s a great time for the dogs to enjoy the water and take a dip.
Rocky Woods sits at the intersection of two watersheds—the Charles River and the Neponset River—making it home to wetlands that support a thriving mix of wildlife, including frogs, turtles, beavers, and songbirds. Our dogs were very curious about the frogs and tadpoles on the shoreline.
The trail opens into wide, pine-covered paths, where shade is plentiful, as you make your way to the Cedar Hill overlook at 2.1 miles. There’s one steep stretch here to get to the view, but it’s not technical—just a wide path with a steep incline.
After taking in the view, enjoy the downhill stretch to Chickering Lake at 2.8 miles, where the dogs can have one last swim and sip before arriving back at the parking lot.
What makes this trail especially nice is its easygoing nature: it’s a hike that offers interest and variety without being strenuous or technical. It’s well-marked and well cared for. We saw only a few others with their dogs off-leash, yet under control and enjoying the trails.
🧭 TURN-BY-TURN DIRECTIONS 🧭
- Start the trail to the left of the kiosk (south side of the parking lot). Follow the yellow blazes and “Loop” sign.
- At 0.18 miles, turn left, following signs for Echo Pond Trail.
- At 0.28 miles, stay to the left to walk along the left side of Echo Pond.
- At 0.6 miles, turn right, following the East/West Trail sign.
- At 0.63 miles, bear left at number “16” on the tree.
- At 0.77 miles, bear right, following signs for June Pond Trail.
- At 0.95 miles, turn right at the fork, following
signs for theblue-blazes and the sign for thedRidge Trail.
- At 1 mile, bear left to continue
onfollowing signs for the Ridge Trail.
- At 1.52 miles, turn right to continue on the blue-blazes, following signs for the
dRidge Trail.
- At 1.55 miles, bear left, continuing to follow the Ridge Trail sign and yellow blazes.
- At 1.95 miles, bear left on the wide, gravel path then stay left again, following the signs for Tower Trail and Cedar Hill Overlook.
- At 2.17 miles, bear left to follow the sign to Cedar Hill Vista (this is the steep section heading up to Cedar Hill).
- At 2.25 miles, after taking in the view of Cedar Hill, continue on the wide path as it bends around to the right.
- At 2.3 miles, turn right then take a quick left following signs for Cedar Hill Trail.
- At 2.5 miles, bear right, following signs for Noanet Trail.
- At 2.72 miles, bear left on the gravel path, then stay to the right (away from the Private Property sign) and follow straight out to the parking lot, stopping for one last swim on the way.
That's it, friends! I hope this trail guide for the Rocky Woods Reservation Ridge & Cedar Hill Loop gives you all the info and inspiration you need for a fun and successful hike here.
Please feel free to leave any questions or comments below. I'd love to hear if you end up hiking here and how you like it! :))
Happy Trails! 🐾🐶🥾
