Three Awesome Small Towns, Best Seen by Road Trip

In the past few weeks, I’ve spent plenty of time in small towns. They’re the kinds of places you only visit on a road trip, when passing through, going to bigger cities and bigger sites that aren’t sequestered below the Mason-Dixon, far from a major airport or hidden, for example, in rural Mississippi. (I’ve never heard my friends, otherwise adventurous types, talk about catching the next flight out of New York to Tupelo.)

But there are great travel experiences to be had in small-town America, where you don’t need a lifetime to peel back the layers of history like you might in Philadelphia or Boston. These small towns are manageable, navigable and just plain visitable. (It helps that every single person I met was super-friendly too.) These towns, all with fewer than 50,000 residents, have been some of my favorites stops on the trip, and here’s how to see them.


Natchez, Mississippi
Natchez is, as it’s always been, a quintessential river town. A little bawdy, rough around the edges and a stopping point by definition: It’s at the head of the Natchez Trace Parkway. There’s not much to do here but wait for the next ship to come in, whether its a coast guard cutter–there’s one stationed here–or a boatload of luck at the Isle of Capri, a smoky riverboat casino that provides some contact with the gambling past–and present–of the Mississippi.

What often happens, though, is that visitors set up headquarters at the Natchez Grand Hotel and simply slow down. If they’re feeling adventurous, there are antebellum mansions to tour because the town surrendered to General Grant in the Civil War, sparing its buildings to watch history, like the river, wash on by. The even more intrepid visitor will brave the Under the Hill Saloon, a honky tonk with guest rooms upstairs that come with a disclaimer: “One demanding complete silence before 2 a.m. should probably stay elsewhere.”

Tupelo, Mississippi
On first glance, there’s one thing to see in Tupelo, Mississippi. Elvis’ first home is here, a two-room shack built for $180, where the singer was born January 8, 1935. But a downtown arena–where The Eagles, Tom Petty, Cirque du Soleil and Bill Cosby have played since its opening in the 90s–has sparked new development, with restaurants and bars taking up storefronts where stalwarts like Reed’s Department Store and Booth’s Tupelo Hardware Company still carry on.

Nautical Whimsy is a wine bar and Italian bistro, while 212 Cafe does a fantastic lunch and brisk coffee business starting at sunrise. Romie’s, a local BBQ titan, has a new location on Troy Street, around the corner from Fairpark Grill, a perhaps surprisingly good steakhouse and bar. (The small business world isn’t all success stories: Joe Joe’s Espresso went under recently but still sells fantastically roasted beans to 212.) Not bad for a town of 40,000, halfway to Nashville along the Trace.


Paducah, Kentucky
In Western Kentucky, at the confluence of the Tennessee and Ohio rivers, Paducah is a town of just 25,000, not quite 200 years old, founded by William Clark, of Lewis and Clark renown. But the last 20 years have turned it into a creative capital under even the most powerful of radar. Thanks to talkative artists who have taken up residence there, word is starting to leak out about this enclave by the rivers: The town was recently named one of the National Trust for Historic Preservation’s 12 destinations of distinction. The recognition, says the Trust, guarantees “an authentic visitor experience [featuring] dynamic downtowns, cultural diversity, attractive architecture, cultural landscapes and a strong commitment to historic preservations, sustainability and revitalization.” Sounds like Paducah!

A city-sponsored artist relocation program has turned the LowerTown neighborhood into a gallery hopper’s dream, just a few blocks from downtown, with dozens of homes and studios to visit. The biggest ticket in Paducah may be the National Quilt Museum–it has more thrills than you’d expect!–but creative local businesses are making small-town life exciting: Max’s serves outstanding brick-oven pizza, Etcetera has the best coffee in town and Kirchhoff’s Bakery is a family-run institution, re-opened in its original location after 40 years with the ovens off.

The city center is quite manageable by foot, but the city tourism bureau has put together a cell phone walking tour that lets visitors dial in for more info as they explore historic shop buildings, theaters and churches. (The number is 270-854-3050. Try it now!) More importantly, it’s a small enough town that people will happily strike up a conversation with you, just to find out what the heck you’re doing in Paducah. More often than not, it’s someone fascinating, like Shane Lee, the clothing designer I met while getting a cup of coffee. For personal connections and experiences like that, maybe it is worth hopping a plane to flyover country.