The Best Ghost Towns to Visit in Massachusetts

Find out if you're getting ripped off on your car insurance in less than two minutes.
Find insurance savings (100% Free)
No long forms · No spam · No fees
Why you can trust Jerry
Jerry partners with some of the companies we write about. However, our content is written and reviewed by an independent team of editors and licensed insurance agents, and never influenced by our partnerships. Learn more baout how we make money, review our editorial standards, reference out data methodology, or view a list of our partners
Massachusetts is home to everything from colonial-era history to pumped-up Boston sports fans. Whichever scene’s more your style, there’s something here for you in terms of haunted spots and ghost towns. 
Here are the tales of Dogtown, Questing, Quabbin Reservoir, and Whitewash Village, alongside travel tips for visiting them. 
If you’re planning to visit these fascinating ghost towns all in one trip (or trying one at a time on a weekend splurge), make sure you have the right car insurance to stay protected as you journey. Looking for a better policy? Jerry can find you a new one in minutes—and for free!
Here, Jerry explains everything special (and sometimes downright supernatural) about four of the best Massachusetts ghost towns.


Black and white harbor, large crane arm above wooden building
Gloucester Harbor, Massachusetts

What is the story of Dogtown?

The state government records that Dogtown was settled by Europeans in 1623. The “Commons Settlement,” as it was called, used its rocky inland location for protection from pirate attacks and hostile tribes. 
Multiple legends survive to explain Dogtown’s name (which wasn’t widely adopted until the 20th century, long after its abandonment). 
Some believe that the wives of sailors and Revolutionary War-era soldiers kept dogs for safety and companionship, and after they left or died, the dogs became a feral group that roamed the area thereafter.
Between 1750 and 1800, 50-100 families lived in the area in modest homes. Many were farmers or fishers, and as travel became easier and the threat of British coastal attacks subsided after the War of 1812, many residents of Commons Settlement left for the harbor or to move west.
The story goes that as the financially able left, only poor and unscrupulous individuals remained. Single or widowed women who stayed behind allegedly practiced witchcraft. These people—vagrants, renters, or loner types—may also have been the “dogs” of Dogtown.
Today, you can explore a huge park where Dogtown once stood. Carved stones and old cellar holes are still visible. Members of the current generation intent on preserving Dogtown’s creepiness have added a toy cemetery full of old dolls and stuffed animals.

What makes Dogtown special?

Dogtown is a true chilling ghost town replete with legends of witchcraft, pieces of pre-Revolutionary War history, and even modern tall tales.
  • Locals claim to have seen a massive gray wolf-like apparition in 1984. They found a mutilated deer (torn apart but not eaten) on the beach—and someone saw the monster galloping into the nearby woods
  • Visit the Dogtown Common park, where you can walk, bike, and cross-country ski beside old cellar holes and engraved stones. The park is open from dawn to dusk and is pet-friendly.

How to visit Dogtown

From Gloucester, take Route 128 to the Grant Circle Rotary. Take the exit toward Lanesville to hop onto Route 127. Then turn right into Poplar Street, turn left onto Cherry Street, and continue just over a mile to park on Dogtown Road
Pro Tip Before you begin your adventure, stop by the Gloucester Office of Tourism to grab a Dogtown Common Trail Map. Their phone number is (978) 282-4101. 
Thousands of customers saved on average $887/year on their car insurance with Jerry
This app is great, but the customer service is even better! Not to mention convenient! My husband and I got the lowest rate (much lower than the rates I was finding online through my own searches), quickly, and pretty much all through text message! Thank you so much for a hassle free experience👍
Gabriella R.
Find insurance savings (100% Free)
rating primary
4.7/5 Rating on App Store


Ski lift over town, river flowing through the middle
Ski Lift, Massachusetts

What is the story of Questing?

This early colonial settlement was named for the Questing, an uncatchable beast in King Arthur legends. Questing was the birthplace of the first children of European settlers in the New Marlborough area. 
There doesn’t appear to be a dramatic story to Questing’s decline: it seems that the village was abandoned in the late 1800s as its inhabitants simply moved further west
The untouchable magic of the Questing beast is still visible in this now-idyllic natural area: visitors can enjoy a nationally recognized wildlife preserve with hardwood forest, wildflower fields, and natural springs and pools.
Today, you can follow a walking path to view the town’s ruins and some spectacular nature. One prominent building that remains is the Leffingwell family homestead, which features cellar holes and stone walls.

What makes Questing special?

Questing is a beautiful and well-recognized 438-acre nature preserve with plenty to do, including:
  • Dog walking, hiking, birdwatching
  • Skiing and snowshoeing
  • Special guided events such as “Owl Prowls” and “Full Moon Adventures”

How to visit Questing

From New Marlborough, take M-183 to New Marlborough Hill Road. You’ll run right into the Questing entrance.
(New Marlborough is about an hour west of Springfield.)

Quabbin Reservoir

Midshot, river framed with tress and a rocky beach on the left and right
Quabbin Reservoir, Massachusetts

What is the story of Quabbin Reservoir?

Quabbin Reservoir covers what used to be four towns: Dana, Enfield, Greenwich, and Prescott. The towns’ residents would have happily continued their lives there—if fate (in the form of bureaucracy) hadn’t interfered. 
Boston and its suburbs noticed that drinking water was becoming scarce in the 1920s. Officials determined that they would need to create a new reservoir—and the four towns sat on the perfect land to flood. 
All four towns campaigned to have the reservoir relocated, arguing that the money needed to exhume and relocate thousands of dead bodies (among other costs) would make the transition too expensive, but the state decided to go through with its original plan. 
After each one held a special good-bye celebration filled with storytelling and dancing, the towns ceased to legally exist and were flooded in 1938. Most structures, except for Native American burial grounds and select buildings, were cleared away before the water took over. 
What’s left of Enfield and Greenwich is completely lost under the water, but some features of Dana (the town at highest elevation) are visible, including an old cellar.
Once a year, the Swift River Valley Historical Site puts on a tour where the public can see the Prescott town hall.

What makes Quabbin Reservoir special?

  • The 39 blue acres of Quabbin Reservoir make it a popular spot for fishing and boating and are considered a beautiful (though manmade) natural area
  • Dana Commons, officially settled from 1763-1938, is on the National Register of Historic Places
  • In Dana Commons, you can walk trails which include pictures and signs detailing the buildings that once stood in the area
  • The Swift River Valley Historical Society has a museum honoring the four towns. It’s open to the public during limited hours 

How to visit Quabbin Reservoir

There are several ways to access the Reservoir’s different boat launches or Dana Common. 
To reach the historical site, head along Route 32A in Petersham and park at Gate 40
You can see old homes, the town hall, school, and a hotel. If you’re curious about the names of past residents, head over to Quabbin Park Cemetery in Ware.
The Swift River Valley Historical Society is located north of the reservoir, off of Elm St and Hessian Lane in New Salem

Whitewash Village

Boats on foggy water, crop of land coming from the left side.
Chatham, Massachusetts

What is the story of Whitewash Village?

Whitewash village was inhabited from 1711 to roughly 1860. Its name probably comes from whitewashed rocks or buildings on Monomoy Island. 
Life on the island was rough, and it was initially merely a haven for shipwrecked or traveling sailors. Accordingly, Stewart’s Tavern was one of the first major buildings there.
Later on, Whitewash grew into a community of around 200 people known as “Powder Hole Harbor.” Fishing was unsurprisingly their main source of income, and fishermen sold cod and mackerel to the bigger cities inland. 
Alongside two wharves, there was a school, inn, and other public amenities.
Despite the harsh weather that made sailing and living near Monomoy taxing, the real challenge came in 1860, when a winter storm changed the coastline. Sand filled the harbor, making it harder to launch boats. Gradually, the inhabitants packed up and left to go inland.
After its 19th-century abandonment, Whitewash Village became property of the US government. It was the Monomoy Island gunnery range during 1944 in World War II. Later, in the 1970s it became a US Fish and Wildlife Service national refuge. 
Today, most of the original buildings are gone thanks to the region’s rough weather, but Monomoy Island is a beloved destination for wildlife viewing and fishing.

What makes Whitewash Village special?

Monomoy Island is a national wildlife refuge. Today, you can:
  • Fish (including sport fishing)
  • Watch for wildlife including seals, whales, and migratory birds
  • Take a Monomoy Island Ferry Boat Ride or go on a special shark tour 
  • Visit Monomoy Point Lighthouse, one of the only long-lasting structures on the island

How to visit Whitewash Village

Whitewash Village’s ruins are mostly underwater, but Monomoy Island is still well worth a visit.
The island is located off of Chatham. Drive from US Route 6 East to State Route 137 South. Then take State Route 28 East to the rotary. Take the Main Street exit to Shore Road. Turn right and proceed past Chatham Lighthouse to reach the island access point.

Find affordable car insurance

While you’re busy traversing the Old Bay State, don’t let a blown tire, fender bender, or other unexpected incident ruin the trip. Don’t blame it on a ghost (even if there was one)—instead, pick a high-coverage, affordable insurance policy from the get-go!
Jerry can find you a more affordable policy with just a few swipes and clicks. Just enter a few pieces of information, and Jerry will present you with your current policy and dozens of competitive quotes. 
Chose the one you like best and—just like that—Jerry will get all the paperwork for you to register your new policy. They’ll even help you break up with your old insurer!
“I heard about Jerry through a podcast and decided to try it out. My 2008 Range Rover Sport was costing me $168/month before Jerry found me the exact same coverage for $84/month under Plymouth Rock. I’ll definitely keep shopping for insurance with Jerry.” —Eileen P.
kemper logo
Jerry Rating
See rates
nationwide logo
Jerry Rating
See rates
progressive logo
Jerry Rating
See rates
travelers logo
Jerry Rating
See rates

Easiest way to compare and buy car insurance

No long forms
No spam or unwanted phone calls
Quotes from top insurance companies
Find insurance savings — it's 100% free