Connecticut’s quirky small towns are defined by their unusual names, eccentric local landmarks, and offbeat festivals rather than by any official designation. While there is no state registry of “playfully peculiar” places, several towns and villages have earned reputations for their oddities—from a town named after a mythical sea creature to a village that legally changed its name to a Christmas carol. This article highlights the most genuinely peculiar places in the Nutmeg State and explains what makes each one stand out.
What Makes a Town “Playfully Peculiar”?
Peculiarity in Connecticut usually comes from three sources: an unusual name, a strange historical event, or a quirky modern tradition. A town might have a name that sounds funny out of context (like Barkhamsted), host a festival celebrating an odd local product (like Deep River’s Fiddlers’ Convention), or contain a village whose identity is tied to a joke that stuck (like Christmas Village). These traits make a place memorable to visitors and proud residents alike, even if the official town government has nothing to do with the whimsy.
Towns With Unusual Names
- Mystic – Though not a town (it spans Groton and Stonington), its name evokes the supernatural, and it leans into that with the Mystic Seaport and a famous sea monster legend. The name likely comes from the Pequot word “missi-tuk,” meaning “great tidal river,” but the modern association with mystery is purely playful.
- Barkhamsted – This rural town’s name sounds like a dog kennel, but it actually derives from the English village of Barkham in Berkshire. Locals embrace the canine pun with an annual “Barkhamsted Dog Parade” every June.
- Uncasville – Named after the Mohegan sachem Uncas, the name sounds like “uncommon” to some ears. It’s the home of the Mohegan Sun casino, which adds a modern twist to its historical name.
- Bantam – This village in Litchfield shares its name with a small chicken breed, and the local diner, Arethusa Farm, actually keeps bantam chickens on display. The name comes from a Native American word for “bold,” but the poultry association is hard to ignore.
- Noank – A coastal village whose name sounds like “no anchor,” which is ironic for a fishing community. The name is likely from the Pequot word “nauank,” meaning “point of land,” but sailors joke that the harbor is too rocky for anchoring.
Villages That Changed Their Names for Fun
One of the most literal examples of playful peculiarity is Christmas Village, a small neighborhood in the town of West Haven. In 1995, residents of a 20-home street petitioned to rename their community “Christmas Village” to attract holiday tourists. The name stuck, and the village now hosts an annual Christmas tree lighting and carol sing-along, even though it’s not an official municipality. Similarly, the borough of Fenwick in Old Saybrook is known for its “Toadstool” houses—a cluster of whimsical mushroom-shaped cottages built in the 1920s. The name Fenwick is not unusual, but the architecture is so quirky that the neighborhood is a local landmark.
Festivals That Celebrate Odd Local Traditions
- Deep River’s Fiddlers’ Jamboree – Held every July, this festival celebrates old-time fiddle music, but its real quirk is the “Fiddler’s Parade” where participants dress as instruments. It’s one of the oldest continuous folk festivals in New England.
- Essex’s “Shad Derby” – This May festival honors the shad fish, which once spawned in the Connecticut River. The derby includes a parade with a giant shad puppet and a “Shad Queen” crowned in a ceremony that is equal parts earnest and absurd.
- Mystic’s “Sea Monster Hunt” – In 2013, the Mystic Chamber of Commerce sponsored a fake sea monster sighting in the Mystic River, complete with a blurry photo and a reward for capture. It was a publicity stunt, but it revived the town’s old legend of “Sock” the sea serpent, which had been reported in the 19th century.
Architectural Oddities and Landmarks
Connecticut’s peculiarity is also visible in its built environment. The Gilbert’s Castle in Eastford is a 19th-century stone tower built by a local eccentric who believed the world would end in 1881; he built the tower to observe the apocalypse. Today it’s a state park. In New Haven, the “Whale” building (officially the Long Wharf Theatre) has a wave-shaped roof that locals say looks like a beached whale. And in Litchfield, the “Milk Bottle” building is a former dairy store shaped like a giant milk bottle, now a coffee shop. These structures are not official landmarks, but they define the towns’ quirky character.
How These Towns Compare to Other Quirky New England Towns
Compared to Vermont’s “Pie” town (Pie Town is actually in New Mexico) or Massachusetts’ “Blandford” (which is anything but bland), Connecticut’s peculiar towns are more understated. They don’t have a town named “Nothing” or “Why,” but they have a higher density of colonial-era names that sound funny to modern ears (like Wethersfield or Poguonock). The difference is that Connecticut’s quirkiness is often tied to its maritime and industrial history, rather than pure whimsy. For example, Mystic’s sea monster is rooted in actual 19th-century newspaper hoaxes, while Deep River’s shad festival is a genuine celebration of a fish that once fed the town.
Common Misconceptions About Connecticut’s Quirky Towns
A common misconception is that “Christmas Village” is a separate town; it’s actually just a neighborhood. Another is that “Mystic” is a town; it’s a village and a census-designated place, not a municipality. People also assume that “Bantam” is named after the chicken, but it’s a Native American word. Finally, many think that “Noank” means “no anchor” in English, but it’s a Pequot word. These misconceptions are harmless, but knowing the real origins adds depth to the playful reputation.
Frequently Asked Questions
What is the most oddly named town in Connecticut?
Most people point to Barkhamsted because it sounds like “bark ham sted,” evoking dogs and ham. But Noank and Bantam are close runners-up. The official “oddest” is subjective, but these three are the most cited in travel blogs and local polls.
Is there actually a town called “Christmas Village” in Connecticut?
Yes, but it’s not a town. It’s a neighborhood in West Haven that renamed itself in 1995. It has no municipal government, but it does have a community association that organizes holiday events.
Can you visit the mushroom houses in Fenwick?
The “Toadstool” houses are private residences on private streets. You can drive by or walk on the public sidewalk, but you cannot enter the properties. The best view is from the water or from the end of Fenwick’s main road.
Are there any towns that celebrate their oddity with a museum?
Yes, Deep River has the “Shad Museum” (officially the Deep River Historical Society’s Shad Room), which displays fishing gear and memorabilia from the shad industry. It’s open by appointment and is as quirky as it sounds.
Do any of these towns have official “sister city” agreements based on their names?
No, but Barkhamsted has a loose cultural exchange with Barkham, England, though it’s informal and not an official sister city. The connection is mostly historical, as the town was named after the English village.
Conclusion: Embracing the Quirk
Connecticut’s playfully peculiar towns are best enjoyed by driving through them, stopping at their local diners, and chatting with residents who are happy to explain the local joke. Whether it’s the sea monster of Mystic, the shad of Deep River, or the Christmas lights of West Haven, these places prove that New England’s charm often lies in its refusal to take itself too seriously. For a day trip, start in Mystic, head north to Deep River, then west to Barkhamsted, and you’ll have seen the state’s finest oddities in a single loop.
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