Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop
Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop
5.0
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hikers
Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop
01:49
6.73km
90m
Hiking
The Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop offers a delightful blend of natural scenery and historical intrigue, making it a fantastic choice for an easy outing. You'll traverse diverse wooded paths, catch glimpses of the tranquil Walden Pond, and ascend to viewpoints like the Steel Tower Lookout, which provides expansive vistas over the woods and even Boston. The trail is generally accessible, though some sections can be rocky, and it's worth noting that it can get muddy after a good rain.
This 4.2-mile (6.7 km) hike, with a gentle 299 feet (91 metres) of elevation gain, is rated as easy and typically takes around 1 hour and 49 minutes to complete. It's a great option for families or anyone looking for a rewarding experience without a strenuous climb. Remember that access to the top of the Stone Tower and the interior of Dungeon Rock may require contacting park rangers, so plan ahead if those are must-sees for you.
One of the most unique features of this loop is Dungeon Rock, a site shrouded in pirate legends and 19th-century spiritualist excavations for buried treasure. This historical element, combined with the panoramic views from the Stone Tower and Steel Tower, makes the trail stand out in the Lynn Woods Reservation. It's a perfect example of how the second-largest municipal park in the United States blends natural beauty with fascinating local history.
Last updated: June 9, 2026
Waypoints
Start point
Parking
Get Directions
1.01 km
Dungeon Rock
Highlight • Cave
Today you can visit Dungeon Rock which was formerly known as Pirates' Rock by hiking along. Maybe you will find the treasure?
Tip by
2.11 km
Stone Tower
Highlight • Monument
Tip by
3.00 km
Mount Gilead Lookout
Highlight • Monument
Translated by Google •
Tip by
3.03 km
View of Boston from Steel Tower Lookout
Highlight • Viewpoint
Tip by
4.23 km
View of the Island in Walden Pond
Highlight • Viewpoint
Tip by
4.55 km
Serene Riverbank
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
Sunday 19 July
26°C
16°C
0 %
Additional weather tips
Max wind speed: 24.0 km/h
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This route was planned by komoot.
Frequently Asked Questions
How long does it take to hike the Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop?
This loop typically takes around 1 hour and 49 minutes to complete. It covers a distance of approximately 6.7 kilometers (4.2 miles).
Is this trail suitable for beginners?
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.
What are the main landmarks and viewpoints along the route?
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.
What is the terrain like on this hike?
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.
When is the best time of year to hike this loop?
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.
Where can I park for the Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop?
The trail typically starts from Pennybrook Road. There is parking available near the trailhead on Pennybrook Road within the Lynn Woods Reservation.
Is this trail dog-friendly?
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.
Are there any fees or permits required for hiking in Lynn Woods Reservation?
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.
What should I know about Dungeon Rock?
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.
Does this trail connect with other paths in Lynn Woods?
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.
What kind of scenery can I expect on this 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.
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