In the Internet age, cool is decentralized. What was once the sole bragging right of hip urban centers, with their concentrations of creative industries, arts and culture, is dispersing more and more to smaller towns across the country. Tiny and remote Marfa, Texas became a darling of the American art scene, was profiled on 60 Minutes, and the town’s Ballroom Marfa alternative space penetrated Manhattan with the initiative “Marfa Dialogues.” Marfa, in fact, may be too cool—it was neatly skewered on The Simpsons and I Love Dick—but other American towns are just the right balance of charm, breathing room, and that most elusive and prized quality in any travel destination, authenticity.
Manchester, New Hampshire
An obligatory stop for presidential candidates, Manchester's Puritan Backroom restaurant won a 2020 “America's Classics Award,” a James Beard Award recognizing great American restaurants that still have true regional authenticity.
Manchester also offers natural beauty (Lake Massabesic and White Mountain National Forest) and the 1926 splendors of the Palace Theatre, where Chubby Checker once performed. Best of all, Manchester is home to the cool brilliance of Zimmerman House, designed by Frank Lloyd Wright and open to the public.
Williamson, West Virginia
A forward-thinking revelation situated on the Tug Fork River bordering Kentucky, this hamlet of just over 3000 boasts the Williamson Farmer’s Market on Saturdays and a dining scene that includes El Sazon Mexican restaurant, the circa-1968 Tunnel Drive-In and Brooklyn-style coffee houses. Each room at the Mountaineer Hotel, built in 1925, is named after illustrious guests of the past, including Paul Newman, John F. Kennedy and Loretta Lynn. The entire town is on the National Register of Historic Places, and the citizens of Williamson take a light-hearted approach to local history: The Hatfield and McCoy feud inspired a hotel (Hatfield McCoy House) and a festive race, the Hatfield McCoy Marathon.
Clarksdale is the heart of the Delta and the perfect place to experience the African American roots of blues music. The famed “crossroads,” where Robert Johnson—according to legend—sold his soul, is marked by a giant guitar. At the Delta Blues Museum, take in the shack where Muddy Waters grew up. The Riverside Hotel is great for channeling legendary blues artists (Bessie Smith died at the hotel when it was a hospital) and the Shack-Up Inn is an authentic and beat-up shotgun shack. Abe’s BBQ has been a standard since 1924, and the joint is always jumpin’ at Ground Zero Blues Club.
A former mining center and once known as the “wickedest town in the west,” Jerome, a 40-minute drive west of Sedona, became a kind of ghost town before it was rejuvenated by post-hippies. The Jerome Historical Society saved the buildings in “Ghost City” and created a town that’s akin to a free-floating museum, starting with the event space “Spook Hall,” set in a former J.C. Penney. At “Art Park,” local residents sell such handicrafts as handmade jewelry. For most visitors, the Jerome Grand Hotel, located in a 1920s building, is the right atmospheric choice: The hotel also features the accomplished Asylum restaurant.
San Luis Obispo, California
The center of cool in this pretty California town is the Madonna Inn, a remarkable high-kitsch affair with rooms done up in individual themes, such as the “Caveman Suite” (lots of animal prints) and the pink-beyond-measure “Love Nest.” Retro fare like Shrimp Louis is available at the Madonna Inn’s Copper Café, and the hotel’s Gold Rush Steakhouse is pure spectacle. San Luis Obispo is full of diversions, from “Bubblegum Alley” (a 70-foot-long alley of gum sculpture created by visitors) to such restaurants as Mee Heng Low Noodle House. Outside of town, the winery beat includes such standouts as Autry Cellars.