Tucked away on Cape Ann, Massachusetts, Dogtown has a rich and fascinating history that dates back to colonial America. Home to everyone from early settlers and suspected witches to today’s hikers and boulderers, Dogtown is a modern-day ghost town that comprises portions of Gloucester and Rockport, preserved in large part by the efforts of Henry Babson, who left his own peculiar mark on the area. Don’t miss the opportunity this spooky season to explore this historic New England ghost town.

Credit: Tim Peck

Dogtown’s Colonial History

Originally known as “the Commons Settlement,” this upland section of Cape Ann was initially used for logging and livestock grazing by residents in the nearby port of Gloucester. As the port community grew in the early 1700s, the Commons Settlement was opened for development, with local residents constructing simple houses consisting of a cellar hole and an above-ground wooden frame.

Located on the main road between Rockport and Gloucester, by the mid-1700s the Commons Settlement reached the height of its prosperity. Due to its location at the center of Cape Ann, many considered it the best part of town. Sixty of Gloucester’s most prominent families lived along Commons Road.

Following the Revolutionary War, however, the Commons Settlement population began to decline—the land, already strewn with boulders from the terminus of a glacier that had once covered the region, wasn’t particularly favorable for farming while most of the trees had been cut down for timber or to provide grazing lands. There were also better economic opportunities elsewhere, with the port of Gloucester a few miles away offering residents more lucrative work in fishing, shipping, and other industries.

As the Commons Settlement’s original families moved away, the less prosperous—such as ship crews, freed slaves, and widows who could not afford to live near the harbor—began to take their place. It was said that roughly 60 widows of Revolutionary soldiers resided in Dogtown. Soon, the once-prestigious area became better known for its poverty.

The Witches of Dogtown

With its population changing and dwindling, Dogtown became more culturally and socially isolated. Between the extreme poverty, the houses literally falling into ruins, and some of the elderly widows working as herbalists and healers, it wasn’t long before some of Dogtown’s new residents were suspected of witchcraft.

The best-known of the Dogtown witches is Thomasine “Tammy” Younger. Referred to as “the Queen of the Witches,” Younger lived on the main road that passed through Dogtown near what is now Cherry Street and would tell fortunes, entertain men, and host card games. She would also act as a toll keeper—threatening to curse passersby unless they gave her goods or money. Upon Younger’s death, the cabinetmaker tasked with building her coffin felt an evil spirit in his presence and believed she was still lurking around.

Judith Rhines is another of the well-known Dogtown witches. Her witchy reputation was likely gained by her fortune-telling and lifestyle. Rhines was believed to be one of three women that made up Dogtown’s red-light district. Rhines also lived (and was rumored to have a romantic relationship) with Cornelius “Black Neil” Finson, a freed slave.

Another Dogtown witch, Peg Wasson, was accused of flying around on a broomstick or in the form of a crow. Legend has it that, while flying as a crow over a camp of soldiers, she was shot by a soldier with a silver button from his coat—the same silver button was later removed from Wasson’s leg by a doctor.

More than 250 years later, the contemporary embellishment of these women’s reputations is as much a reflection of 18th- and early 19th-century prejudices as it was their actual supernatural powers. Indeed, as Elyssa East writes in her book Dogtown: Death and Enchantment in a New England Ghost Town, “there were two types of women [primarily] who were referred to as witches in eighteenth and early nineteenth-century America: the midwife/folk healer and the social outcast, who was often destitute, accused of licentiousness and of possessing unusual, if not supernatural, power…” All impoverished and living outside contemporary societal norms, Younger, Rhines, and Wasson clearly fit the bill.

Credit: Tim Peck

Dogtown’s Demise

By 1814, just six of Dogtown’s original 80 houses were standing. And in 1830, Dogtown’s last resident—Cornelius Finson—departed. In 1845, the last remaining home in Dogtown was demolished. However, the area, still predominantly open fields, remained a prominent destination for visitors and locals alike.

One prominent visitor was Henry David Thoreau, who visited the area in September 1858. In his journal, he recounted a lengthy walking tour in and around Dogtown. As they traveled through the area, Thoreau’s party “found [them]selves in the midst of boulders scattered over bare hills and fields,” a setting that he described as “ the most peculiar scenery of the Cape.” Of course, that didn’t stop Thoreau and his party from staying in the region after sunset, as they watched the moon rise over Dogtown. As they watched, the moon soon dwarfed the boulders on the horizon that had once seemed immense but now looked “no larger than nutshells or burlnut against the moon’s disk…”

Babson’s Depression Era Project

The chance to experience Dogtown’s spooky history today is largely thanks to Roger Babson, a prominent business leader during the early 20th century who left his own peculiar mark on the community. During the Depression, Babson, a Gloucester local and descendant of some of the first colonists in the area, hired unemployed local quarry workers to find many of the cellar holes and foundations of Dogtown’s colonial residents. In a pamphlet titled Gloucester’s Deserted Village, Babson included a map that numbered each cellar hole his workers found (40 in total), explaining that he’d had the workers carve corresponding numbers on boulders placed near the ruins. This allowed visitors to view each house and to find other area landmarks, including Dogtown Square.

Although Babson found a “pathos and tragedy in the old forsaken cellars of [Dogtown’s] original inhabitants,” his work in the area did not stop there. As he described in his autobiography, Actions and Reactions: An Autobiography of Roger W. Babson, “Another thing I have been doing…is the carving of mottoes on the boulders at Dogtown.” Despite his family saying that he was “defacing the boulders and disgracing the family with these inscriptions,” Babson found “the work g[ave him] a lot of satisfaction, fresh air, exercise, and sunshine,” allowing him to “revert to a boyhood which I once enjoyed when driving cows” in the area. Moreover, the engraving work enabled him “to write a simple book [for posterity] with words carved in stone instead of on printed paper.”

All told, Babson’s quarry workers carved short motivational inscriptions into 36 of Dogtown’s boulders. Among the many moralizing and eccentric mottos that can still be found today are “Get a Job,” “Spiritual Power,” “Keep Out of Debt,” and “If Work Stops Values Decay.”

Credit: Tim Peck

Dogtown Today

Around the same time that Babson was documenting Dogtown’s historic homes and engraving his values on the area’s boulders, he also purchased much of Dogtown. He later donated the land to the City of Gloucester as a park and watershed for the city’s reservoir. As a result of Babson’s actions, visiting Dogtown is a fantastic way to spend a fall day.

These days, hiking is the most common form of recreation at Dogtown. The terrain is mellow, as much of the area is quite flat and the main trails—remnants of the old colonial roads that bisected the area—are wide and smooth. From the main parking lot on Dogtown Road (just off Cherry Street), it’s easy to spot the engraved, numbered boulders (map) as you walk along Dogtown Road toward Dogtown Commons. The cellar holes themselves are typically a few feet off the road, with some more readily discernible than others due to the passage of time, surrounding growth, and the basement’s original depth.

Just past Dogtown Commons—engraved D.T. SQ on an easy-to-see boulder—those interested in Babson’s inscribed boulders should venture off right and do an out-and-back on Babson’s Boulder Trail. Along this trail, many of Babson’s boulders are easy to spot, although finding a few requires a little poking around. As compared to Dogtown Road, expect slightly more challenging terrain on Babson’s Boulder Trail.

In addition to hiking, Dogtown is also popular for mountain biking and bouldering. Three boulders that are easy to find along the main Dogtown circuit are Whales’ Jaw, Peter’s Pulpit, and the engraved-by-Babson “Spiritual Power” boulder. Just right of the Spiritual Power engraving, there are two wonderful warm-ups—a stellar V0 hand crack and a super-fun V1 seam—along with some more challenging options on the boulder’s rear. Whales’ Jaw—a historic destination because it used to look like a whale’s open mouth—has a fun V3 with some difficulties down low. And Peters’ Pulpit has a host of problems ranging from V0 to V6.

So if visiting a ghost town is on your agenda this spooky season, grab your hiking boots, mountain bike, or bouldering pad and head to Cape Ann to check out one of Massachusetts’ most unusual landmarks.