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Tightwad, Mo.

Firefighter outside fire station in Tightwad, Mo. (© Gary Gladstone/Corbis)

Welcome to Tightwad
Back in the early 1900s, the postmaster of this Missouri town 70 miles southeast of Independence got cheated in a deal for a watermelon at the local store. Out of spite, he named the town Tightwad, and the name stuck. That quirky sense of humor remains to this day: The most famous institution around these parts is the Tightwad Bank, which reopened in 2008 with its own product line of hats, shirts and coffee cups.


Chicken, Alaska

Downtown Chicken, Alaska (© James Schwabel/Alamy)

Once a Gold Rush town, Chicken is now a tiny town — population about seven — off the Taylor Highway, southeast of Fairbanks. The name “chicken” likely refers to a ptarmigan; when the post office opened in 1906, the townspeople couldn’t agree on how to spell the state bird, so they settled on chicken, instead. Downtown Chicken has a bar, a post office, a café (try the cinnamon rolls) and a gift shop, where you will likely find a copy of the book “Tisha,” which details the experiences of schoolteacher Anne Hobbs, who lived in Chicken in 1927.

Hell, Grand Cayman
A service station in Hell, Grand Cayman Island (© Nordicphotos/Alamy)
Amid this Caribbean heaven is a small piece of Hell — a strange stretch of black limestone rock that seems very out of place in West Bay. Enterprising locals have set up a devilishly blood-red gift shop next to it with a “Welcome to Hell” sign.
Monkey’s Eyebrow, Ky.
Man in a tobacco field, Monkey's Eyebrow, Ky. (© Gary Gladstone/Corbis)
Monkey’s Eyebrow is a blink-and-you’ll-miss-it kind of place near Padacuh. (There’s a Monkey’s Eyebrow Road, but no signs tell you that you’ve arrived.) How did it get its name? One theory states that a map of Kentucky’s Ballard County looks a bit like a monkey’s head, and this hamlet is about where the eyebrow would be. Others posit that it’s named for a crescent-shaped ridge called Beeler Hill, which is reminiscent of a bushy eyebrow when the grass grows tall. If you’re in the neighborhood, be sure to take a side trip to equally unique Possum Trot.
Hot Coffee, Miss.
During the 1800s, people traveling by horse and wagon from Natchez to Mobile, Ala., would stop at the local inn for a cup of coffee. Eventually named Hot Coffee, this small community off of Highway 532 southeast of Jackson is still serving coffee, but mainly at the general store, where you can also pick up some hoop cheese and moon pies. The inn is long gone. Many of the area’s residents are descended from 18th-century German Baptist settlers who today still live simply, without electricity, phones or cars.
Knockemstiff, Ohio
Cousins stand together, Knockemstiff, Ohio (© Gary Gladstone/Corbis)
This town is likely most familiar to fans of Donald Ray Pollock’s short stories of the same name. The book “Knockemstiff” is a dark, violent collection, which Pollock followed with the novel, “The Devil All the Time,” also partially set in this town where he grew up. Pollock told The New York Times in an interview that the town’s name likely came from a local moonshine, but no one knows for sure. Knockemstiff is an empty, rundown crossroads with a handful of folks living in the area, so it may only live on in the pages of Pollock’s books.  
Hell, Mich.
Town sign of Hell, Mich. (© Jim West/Alamy)
A typical day in Hell, a half-hour’s drive north of Ann Arbor, involves stopping at Screams for an ice cream, eating ultrahot wings at the local restaurant, buying mugs emblazoned with Damnation U, and mailing a postcard at the post office located in the Hell Country Store. About 10,000 people each year come to get the unique postmark, especially around tax time. People in Hell are not shy about capitalizing on the name: On the town’s website you can sign up to be mayor for a day for $100. Before balking at the price, know that the job has benefits. Mayors get horns to wear for the day, 1 square inch of Hell (a deed and a vial of dirt), and an “Official Mayor of Hell” T-shirt with “impeached” stamped on the back.
Cut and Shoot, Texas
The City Hall of Cut and Shoot, Texas (Doyle Welborn/courtesy Wikimedia Commons)
This oddly named town north of Houston has multiple versions of its origin. Many of the stories are long, especially the one on Cut and Shoot’s own website. Suffice it to say it involved an early 1900s religious dust-up among townspeople who did not want an Apostolic preacher to hold services in their community hall. Knives and guns were present (get it?), but it ended without incident. Cut and Shoot is not huge, only about 1,100 residents, but in 2006 it was officially designated a city.