The Coolest Small Towns of 2025

Livingston, MT | Visit Livingston
For Wildsam's inaugural Road Trip Awards we asked a panel of seven expert judges for the places that will make your next voyage through America unforgettable. Here, we're taking a look at Charming Towns, places with a vibrant “main” street, cultural renown and new residents flocking. Bonus points for a mayor on a first-name basis with everyone.
LIVINGSTON, MT
You want it Western? Livingston shall provide. The stately brick main drag glows with old-school neon, echoing with train whistles and a stroll away from the wild Yellowstone River, gliding through town after leaving the national park. (The Roosevelt Arch gateway is less than an hour’s drive south.) Stalwart businesses like Dan Bailey’s Fly Shop (1938) and Bob’s Outdoor (1946) thrive on the town’s sporting and agriculture heritage, while Elk River Books sources new and rare old titles true to Livingston’s mystique among writers and artists. Campione Roman Kitchen, a cozy-corner Italian spot, is one of the best restaurants in the Mountain West.
Traverse City, MI
Gateway town to the magic of Northern Michigan’s rolling dunes along lake waters in Caribbean blues. Leafy drives through storybook towns bubbling with vibrant creative energy.


Florence, AL
Largest city in The Shoals, perched along Tennessee River, has long history of artistry among natural beauty. “Now more than ever it’s a very vibrant creative community,” says our judge, renowned designer Natalie Chanin.
Millerton, NY
Antiques and atmosphere in an urbane village. After pursuing patina at Montage and Millerton Antiques Center, make it a Double Header Cheesy Style burger at classic Oakhurst Diner.
Brooklin, ME
The “boat-building capital of the world,” home to Brooklin Boat Yard and WoodenBoat Magazine, maritime dreamers’ journal. Brooklin General Store is a staple; treasure Blue Hill Books lies just 20 minutes up the road.

Boone, NC
Hit hard by Hurricane Helene, Boone also showcases the Blue Ridge region’s resilience. In every season, this college-town gem contains multitudes, from rowdy football tradition to an annual fiddler’s convention.
Lockhart, TX
This barbecue bastion is fast-emerging as a Hill Country refuge for creative and enterprising Texans. The Kreuz-to-Smitty’s-to- Black’s-to-Chisholm BBQ rotation requires strategy.


Ashland, NE
“This Platte River town down the road from Omaha is one of those places you don’t know you need til you get there. Within Nebraska, it pioneered strategies around tourism and culture; its retail and food offerings are exceptional for a place of its size. Postscript Press stocks fi rst-class paper goods, books and that Italian pencil you suddenly must have. Salt Creek Mercantile is everything for the home, from candles to locally sourced honey. Just around the corner from both, you’ll fi nd Fariner Bakery, a true stunner—one the best bakeries outside of France? Stock up on pastries, fresh sourdough and focaccia and fi nds from the small market; then, take backroads out of town for long, quiet drives, open sky and sunlit rivers and creeks.”
—Erin Austen Abbott, author, Small Town Living
The Road Trips Awards
We scoured the map. We asked our smartest, most well-traveled friends. The results are in.

Read more like this
