(Previous page, cover photo of Acorn Street in Beacon Hill, Boston: Guilherme Nicholas/text overlay and color change/CC BY 2.0)

Don’t get stuck in the city this weekend! This summer, Atlas Obscura and Zipcar have partnered up to bring you inspired day trips in and around major American metropolises. We guarantee there’s something right around the corner that will surprise and delight you.

True kings of the road will appreciate this circuit, which introduces travelers to the idiosyncratic castles of Massachusetts and the surprising stories behind them.

Trip Highlights

  • See the place that inspired Edgar Allen Poe’s “The Cask of Amantillado”
  • Try having tater tots for breakfast
  • Add some board games to your lunchtime feast
  • Visit a castle large enough to have its own drawbridge
  • See a castle small enough to look like a movie set piece


Sullivan’s. (Photo: Dale Cruse/cropped/CC BY 2.0)

1  Chow(der) Down  8:30AM

Sullivan’s, Castle Island, Boston Harbor, MA


Conveniently located on Castle Island, Sullivan’s opened in 1951 and since then has been serving up a beloved menu of classic seafood (think fried clam bellies and clam chowder), hearty sandwiches, hot dogs, burgers and a breakfast menu that, gloriously, includes tatertots. Sullivan’s is open from the last week of February to the last weekend of November from 8:30 to around 9:30. (Sullivan’s sometimes close up shop early due to weather or if there are more “seagulls in the parking lot than cars” according to their website.)

Sullivan’s, 2080 William J Day Blvd, Boston, MA 02127

The view of the fort at Castle Island. (Photo: Robert Linsdell/CC BY 2.0)

2  Seek Safe Harbor  9:00AM

Castle Island, Boston Harbor, MA


You just ate at Sullivan’s; you’re already here! Strategically located Castle Island has been the site of military outposts dating back to 1634. The current fort was built in 1801 by the English and helped protect Boston from the English in the War of 1812. Popular legend holds that an unfortunate fellow was walled up in the fort’s dungeon, and that this inspired Edgar Allen Poe to write “The Cask of Amontillado”. No longer an island, visitors can stroll along a man made walkway or drive across a causeway that connects Castle Island to the mainland. Once islandside, relax on three miles of beach and parkland or tour the fort. Fort tours are available only during summer months. Check the website for seasonal tour schedules.

Castle Island, Boston, MA 02127

Bancroft Tower. (Photo: Anatoli Lvov/CC BY-SA 3.0)

3  A Proper Tower  11:00AM

Bancroft Tower, Worcester, MA


Pose with this diminutive castle to feel like a giant. This odd little 56-foot stone tower looks like an elaborate movie set piece or a playhouse for an especially spoiled child. It is neither. Built in 1900, this tower was erected in honor of George Bancroft, who founded The United States Naval Academy at Annapolis and served as the 17th U.S. Secretary of the Navy. Today the tower is part of Salisbury Park in Worcester. Although never occupied, the tower does include several small rooms which are gated off from the public.

Bancroft Tower, 3 Bancroft Tower Road, Worcester, MA 01609 

A game of Scrabble in progress. (Photo: thebarrowboy/CC BY 2.0)

4  Game Break  1:00PM

The Castle Board Game Cafe, Beverly, MA


Take a break from real castles and build an imaginary kingdom with a game of Settlers of Catan. Or, if Catan isn’t your thing, choose another game from the over 300 offerings at this highly specific cafe. In addition to a game library, the cafe employs a “GameMaster” for the purposes of giving you advice on what games to play and even to help you settle any debates over gameplay.

The Castle Board Game Cafe, 240 Rantoul St, Beverly, MA 01915

Hammond Castle Museum. (Photo: Robert Linsdell/CC BY 2.0)

5  Secret Rooms and a Drawbridge  2:30PM

Hammond Castle Museum, Gloucester, MA


A man’s home is his castle. This one, built by inventor John Hays Hammond Jr. (pioneer of electronic remote control) even has a drawbridge (sadly, not remote controlled.) Hammond built this medieval-inspired castle between 1926 and 1929 on the Atlantic shore and filled it with Roman, medieval and Renaissance artifacts collected on his travels. Now a museum, you can wander through the castle’s many rooms including a secret passageway, Gothic tapestries and an indoor pool. In the courtyard there’s a (formerly) nude statue of Hammond which he had commissioned in the Renaissance style. His wife insisted he apply a figleaf to it for modesty.

Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930

Winnekenni Castle. (Photo: Diane (Beckwith) Zink/CC BY 2.0)

6  Another Man’s Castle  5:00PM

Winnekenni Castle, Haverhill, MA


Fertilizer can grow a lot of things, but a castle is probably the least expected. In 1861, chemist and inventor Dr. James R. Nichols bought Darling Farm, situated on hill above placid Lake Kenzoa in Haverhill, so he could do experiments with the acrid agricultural staple. After a trip to England and Scotland he was inspired to begin building a castle on the grounds in 1873 as a royal summer getaway. Winnekenni Castle, when completed, included a Pompeian-style dining room and Gothic flourishes. A fire tore through the castle in 1967, but the structure, which now belongs to the city, has since been restored. Today the castle is part of the 700 mile Winnekenni Park Conservation area, and is open to the public for occasional events, including monthly psychic nights. Park open year-round, check castle website for events.

Winnekenni Castle, Castle Rd, Haverhill, MA 01830