Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop
Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop
5.0
(1)
5
hikers
01:49
6.73km
90m
Hiking
Explore the Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop, an easy 4.2-mile hike in Lynn Woods Reservation.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
1.01 km
Highlight • Cave
Tip by
2.11 km
Highlight • Monument
Tip by
3.00 km
Highlight • Monument
Translated by Google •
Tip by
3.03 km
Highlight • Viewpoint
Tip by
4.23 km
Highlight • Viewpoint
Tip by
4.55 km
Highlight • River
Tip by
6.73 km
End point
Way Types & Surfaces
Way Types
5.85 km
696 m
166 m
< 100 m
Surfaces
3.96 km
995 m
915 m
681 m
138 m
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Elevation
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Weather
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Today
Saturday 30 May
14°C
7°C
37 %
Additional weather tips
Max wind speed: 16.0 km/h
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This route was planned by komoot.
This loop typically takes around 1 hour and 49 minutes to complete. It covers a distance of approximately 6.7 kilometers (4.2 miles).
Yes, this trail is generally rated as easy. While it's relatively flat with an elevation gain of about 91 meters, be prepared for some rocky sections and potential mud after rain, so appropriate footwear is recommended.
The trail features several notable landmarks. You'll encounter the historic Dungeon Rock, the Stone Tower (a former fire tower), and the Mount Gilead Lookout. From the Steel Tower and Stone Tower, you can enjoy expansive views, including vistas of Boston. You might also catch a glimpse of Walden Pond and a Serene Riverbank.
The terrain is diverse, winding through wooded areas with lush foliage. It includes both single-track paths and wider roads. While mostly flat, expect some rocky sections. The path can become quite muddy after rainfall, so waterproof hiking shoes are a good idea.
The trail is accessible year-round. Spring and fall offer pleasant temperatures and beautiful foliage. Summer is also great, but be mindful of insects. Winter hiking is possible, but conditions can be icy or muddy, so check local weather and trail reports.
The trail typically starts from Pennybrook Road. There is parking available near the trailhead on Pennybrook Road within the Lynn Woods Reservation.
Yes, the trails within Lynn Woods Reservation are 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.
No, there are typically no entrance fees or permits required to access the trails within Lynn Woods Reservation, including this loop. It's a public park for everyone to enjoy.
Dungeon Rock is a fascinating historic rock formation with a man-made cave. Legend says a pirate hid treasure here. Later, Hiram Marble dug a new cave in search of it. During warmer months, park rangers sometimes open the steel door to the cave for exploration; a flashlight is recommended if you plan to go inside.
Yes, the route utilizes several paths within the extensive Lynn Woods Reservation. You'll find yourself on sections of Pennybrook Road, Dungeon Road, Great Woods Road, Burrill Hill Road, and Boulder Path during your hike.
You'll experience a diverse forest park environment within the 2,200-acre Lynn Woods Reservation. The trail winds through natural forestland with lush green foliage and tall trees. You'll also see three active reservoirs, various rock formations, and crags, in addition to the expansive views from the towers.