Entry No. 37 — the Boston file — filed under: ghost-town
Dogtown Common & the Babson Boulders
A 3,600-acre stretch of forest reclaimed from a settlement abandoned by the early 1800s, riddled with numbered cellar holes. During the Depression, eccentric millionaire Roger Babson paid unemployed stonecutters to carve roughly three dozen boulders scattered through the woods with blunt inspirational mottos — 'GET A JOB,' 'KEEP OUT OF DEBT,' 'NEVER TRY NEVER FAIL,' 'HELP MOTHER' — turning a ghost town into an outdoor self-help gauntlet in stone.
The story
In the late 1600s, colonial settlers built 'The Commons' deep in the rocky interior of Cape Ann, placing their homes inland to stay hidden from pirates and foreign warships. But after the War of 1812, when coastal defense was no longer a life-or-death concern, the population steadily migrated down to Gloucester Harbor. Left behind were the elderly, the destitute, and widows who kept ferocious guard dogs for protection—earning the decaying village its morbid nickname. By the 1830s, the last inhabitant had passed away, leaving only stone cellar holes to be swallowed by brush.
Enter Roger Babson in the early 1930s. The eccentric millionaire, statistician, and Babson College founder—whose own ancestors had lived in the settlement—decided Dogtown's spooky reputation for witches and vagrants needed a stern dose of Protestant work ethic. During the Great Depression, Babson hired unemployed Finnish quarrymen to chisel two-foot-tall capital letters into the giant glacial boulders scattered across his land. His family publicly accused him of defacing the wilderness, but Babson ignored them, describing his weird commission as a book of life lessons written directly on rock.
Today, nature has reclaimed the pastureland, turning Babson's stoic lecture hall into a dense, 3,600-acre forest maze. As you walk the overgrown colonial tracks, you'll pass numbered granite blocks marking where 18th-century homes once stood, only to round a bend and be confronted by a massive rock ordering you to 'GET A JOB,' 'KEEP OUT OF DEBT,' or 'HELP MOTHER.' It remains one of New England's stranger woods: equal parts forgotten ghost town, glacial erratic deposit, and stern Depression-era self-help gauntlet.
What it's like
Pulling into the unpaved Cherry Street trailhead lot off Reynard Street, you step straight onto dirt paths where cell service vanishes almost immediately. Wandering the trails without a physical paper map or a pre-downloaded trail guide is a fast track to getting turned around among identical-looking oak trees, granite outcroppings, and unmarked forks. The vibe is quiet, heavy, and distinctly isolated, especially when fog rolls in from the nearby reservoirs. Wear thick pants and sturdy boots, and cover yourself in tick repellent—the tall grass and leaf litter around the cellar holes are notorious North Shore tick habitat.
The move: Park at the Cherry Street entrance and turn the hike into a scavenger hunt for as many inscribed boulders as you can find before the trail forks get confusing — bring a boulder map or download one first.
- 📍 Gloucester / Rockport (Cape Ann)
- 💸 Free
- ⚡ Up for anything
- 🌗 Outdoors
Where: Dogtown Common trailhead, Cherry Street, Gloucester, MA 01930
Hours: Added 2026-07-20 — confirm current hours before you go.
Pair it with
- Paper House — Pair Dogtown's granite-carved moral maxims with a house built entirely out of varnished 1920s newspaper just three miles away in Rockport.
- Yin Yu Tang: A Chinese Home — Follow up a hike through Cape Ann's overgrown 18th-century cellar holes with a fully intact 200-year-old merchant home reassembled in Salem.
- Wenham Museum (doll & model-train collection) — Contrast the eerie, unpaved silence of Dogtown's forgotten woods with thousands of antique dolls and model trains housed inside a 1655 colonial home.
Good to know
How much does it cost to visit Dogtown and the Babson Boulders?
It is completely free to enter and explore; the area is preserved as a public municipal watershed and park.
Where do I park to access the boulder trail?
The primary public access point is the gravel parking area at the end of Cherry Street in Gloucester, which leads directly onto unpaved Dogtown Road.
Why are there numbers carved on some of the rocks?
Before inscribing his inspirational proverbs, Roger Babson mapped the long-abandoned settlement and hired stonecutters to chisel numbers into rocks next to cellar holes to identify where specific colonial families once lived.
What kind of mottos are carved into the Babson Boulders?
There are roughly three dozen carved glacial erratics along the trails featuring blunt maxims such as 'GET A JOB,' 'KEEP OUT OF DEBT,' 'HELP MOTHER,' 'COURAGE,' 'NEVER TRY NEVER FAIL,' and 'WORK.'
Plan a visit & invite your people →
Further reading: Wikipedia · historyofmassachusetts.org · theothercape.com · my.northshore.edu
last checked: 2026-07-20