Wild, weird and wonderful: hiking Gloucester’s Dogtown

Discover the five square mile wooded center of Cape Ann, smack in the middle of Gloucester, its villages and Rockport

Let’s start with the wild part: While there is a trail system, the area is also criss-crossed with unmarked trails and stone walls go hither and yon, a mute testament to the toils of long-ago settlers. Brambly, rocky, scraggly, Dogtown defies parsing easily. I’ve been lost in minutes detouring around wind-fallen trees, followed deer trails hopefully, encountered odd intersections, been asked repeatedly by my hiking companions if I know where the heck I was and loved every minute! If you’re less comfortable with uncertainty than I am, a map can be found here. The numbered intersections are handy ways to reorient yourself, but be forewarned that some of the signs are removed by locals more happy to navigate by instinct or habit. 

Which brings us the Babson Rocks and the weird part. Imagine you are walking through the woods and you come across a glacial erratic – that’s a big rock sitting all by its lonesome – and as you pass you notice the words HELP MOTHER carved boldly in neat block letters on one side. What you’ve just discovered is one of 16 Babson Boulders, the work of Babson College founder and Gloucester benefactor Roger Babson. Viewing all 16 will take some industry on your part – and you will see an INDUSTRY-inscribed boulder in the process. A map of the Boulders can be found here.

Oh, and did we mention witches? Oh yes, several women who lived in Dogtown in the early 1800s were suspected of witchcraft, and lost hikers have claimed to hear a cackle occasionally coming from the woods.

But let’s get back to the wonderful part: Once you get your bearings, it’s possible to ride a bike from Gloucester to Lanesville or Rockport without a car in sight. There are loops from a mile to 5 miles that traverse scrub, wetlands, hardwood forests, and there are entrances in Gloucester, Annisquam, Lanesville and Rockport. Hikers will pass old landmarks like Whale’s Jaw – sadly no longer identifiable as its namesake as the rock formation collapsed years ago – Peter’s Pulpit and Andrew’s Rock.

Our hike today is a loop that will cover the central part of Dogtown and is easily accessed from Gloucester. First, locate Cherry Street off of Route 128 and follow it to the Dogtown Commons entrance – there is a sign on Cherry Street. Drive up the road and you’ll find parking near the end, or, if there aren’t any available slots, backtrack to the parking lot by the entrance. Follow the route shown below and enjoy the meandering trails as you pass through the woods, spotting signs of civilization from years gone by.

If you like to have a good old hardcopy map on hand, they are available at the entrance, but the supply is not reliably replenished. A quick print-out of an official map may be reassuring to have tucked away in your backpack.