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Explore the mysterious Dogtown woods, visiting multiple historical points of interest like the Babson Boulders.

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181' 55 m


62' 19 m


262' 80 m


262' 80 m



Avg Grade (1°)


Max Grade (6°)

Dogs Leashed

Features Birding · Fall Colors · Historical Significance

Open sunrise to sunset, daily.


Whether its the spooky lore surrounding these woods since its settlement by colonists in 1693 or the extensive, sometimes confusing, maze of trails, Dogtown has largely remained a local's spot and there's nothing quite like it on the North Shore.

This moderate loop run traverses this Essex National Heritage area, distinguished by its beautiful, quiet stretch of forest between Rockport and Gloucester, making it a great option for folks who are looking for solitude and maybe don't mind getting a little lost.

Need to Know

Multi-use trails.

Runner Notes

Great spot for a secluded run, though some trails can be unmaintained with very uneven tread.


From the parking area off Cherry St., head further into the woods along a nice stretch of uphill road. Because this run is a loop, folks can decide to stick to this clockwise routing (as mapped) or do it in reverse. Doing it in reverse gets to the Babson Boulders first, while this routing saves them for last.

For this run, continue straight onto the wide, unimproved Dogtown Road. After 0.7 miles, keep an eye out for the spur trail to the "Never Try Never Win" boulder and the Jas Merry gravestone from 1892.

Continue along Dogtown Road to the northeast to the Dogtown Square intersection. Stay left, continuing onto Wharf Road as it winds north to intersect with Common Road (Wharf Road splits, stay right, though either section will get to Common Road).

Turn right onto Common Road, a wide unimproved road, toward Peter's Pulpit.

Continue north toward intersection 16 onto the Luce Trail to head to the Whale's Jaw, a glacial erratic (granite boulder leftover from a melting glacier) that split after an uncontrolled fire in 1989, losing its namesake resemblance.

Stay to the right at the intersection with the Denison Trail Connector and continue toward intersection 18. This marks the northernmost point of this loop run. Continue along the Luce Trail as it bends to the east (right) and look for the Briar Swamp Trail heading right (south).

The Briar Swamp Trail skirts along the eastern side of Briar Swamp before passing the Boardwalk section and an intersection with the Luce Trail and Nellie's Trail. Turn left onto Nellie's Trail, which is riddled with rocks and roots to watch your footing on. After 4.3 miles, look for the spur trail to the Prosperity Follows Service boulder and the intersection with Dogtown Road. Take the road for a short section before heading left onto the Babson Boulder Trail.

This is one of the more popular trails in Dogtown due to the namesake Babson Boulders, which dot the sides of the path, sometimes facing the opposite direction. These boulders were charitably commissioned by Roger Babson during the Great Depression in order to help stimulate the stone cutting industry of this area.

Enjoy the downhill stroll through this stretch of woods before returning on the Old Gravel Road along the northeast boundary of the Babson Reservoir.

History & Background

Settled by colonists in 1693 until it's abandonment in 1830.


Land Manager: City of Gloucester, MA

Shared By:

Zander Göpfert

Trail Ratings

  3.5 from 4 votes


  3.5 from 4 votes
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in Massachusetts


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Current Trail Conditions

Add Your Check-In


Oct 22, 2020
Ronan Kelly
Western side of the loop is easily navigable but on the Eastern side of the loop, you'll be on secondary trail which is slow going. 5.6mi — 2h 00m
Jun 27, 2020
David S
lots of thorns along the trail. started off the wrong way, but was pretty obvious once backtracked. pretty flat but with technical rocky regions 6.6mi — 1h 41m

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