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Routes
Hiking trails & Routes
Essex County
Lynn

Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop

Routes
Hiking trails & Routes
Essex County
Lynn

Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop

Easy

5.0

(1)

5

hikers

Pennybrook Road to Steel Tower, Stone Tower, Dungeon Rock Loop

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

A

Start point

Parking

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1

1.01 km

Dungeon Rock

Highlight • Cave

Dungeon Rock is full of history and mystery! In the middle of the 17th century, four pirates – one of them named Thomas Veale – sailed up the Saugus River …

Tip by

2

2.11 km

Stone Tower

Highlight • Monument

The Stone Tower is the highest point in Lynn Woods Reservation. Climb the stairs on top of tower to enjoy the impressive views of Boston skyline.

Tip by

3

3.00 km

Mount Gilead Lookout

Highlight • Monument

Unfortunately, you can no longer climb the tower.

Translated by Google •

Tip by

4

3.03 km

This lookout near the Steel Tower is a short climb from the trail and offers panoramic views over the woods, Boston, and the ocean. The structure is basic but sturdy—worth …

Tip by

5

4.23 km

View of the Island in Walden Pond

Highlight • Viewpoint

There’s a small island in Walden Pond that you can see from this point on the trail. The views of the lake are especially beautiful during autumn, and sunset is also a great time to visit.

Tip by

6

4.55 km

Serene Riverbank

Highlight • River

well in woods by side of road

Tip by

B

6.73 km

End point

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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

Elevation

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

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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.

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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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