Small town hospitality meets historic charm at the iconic Main Street.
Every community has its Main Street, where essential transactions take place, stories are swapped over coffee, and delicious meals are enjoyed among friends and families. While some Main Streets have lost their luster, taking a back seat to big city development, others celebrate their history, embrace preservation-based economic development, and are enjoying new vitality. Cooperating with Main Street America, a program of the National Trust for Historic Preservation, prominent buildings are being artfully restored and reused for offices, retail settings, and exciting new coffee shops, bars, and restaurants. These are a few of our favorites across the South.

Main Streets Across the South

Historically Hip | Hammond, Louisiana
Although Hammond was established in 1818, the railroad’s arrival in 1854 transformed this town into a transportation hub and eventually a tourist destination. Where the railroad tracks meet Thomas Street today, you’ll find beautifully renovated Victorian, art deco, and mid-century modern architecture. Along with its shops, Hammond has become “historically hip.”
When it comes to the town’s culinary culture, it’s said that if you’ve discovered Tope La and Streetside restaurants, you’re on the right path. Tope Là offers exceptional Creole Cajun cuisine, while Streetside Market, reminiscent of an open market, serves both Southern and internationally inspired specialties. Also important are Luma Coffee Roasters in the restored Rexall Drugs building, offering delightfully casual meals. Plus, you won’t want to miss the Voodoo pizza from Tommy’s on Thomas. True to Louisiana, this house special is made with Creole barbeque sauce, then topped with alligator sausage and much more. So delicious it’ll put a spell on you. If you’re in town on Saturdays, you can enjoy all of this plus the weekly farmers market.
Southern Delights | NewTown Macon, Georgia
Settled 17,000 years ago along the Ocmulgee River, NewTown Macon is where extraordinary history and remarkable culture come together. Home to Otis Redding, Little Richard, and Allman Brothers Band, the town is also adjacent to the Ocmulgee Mounds National Historic Park.
If you’re feeling a touch peckish, H&H Soul Food is extolled for its stick-to-ya-ribs soul food including the Red Dog (biscuit, fried chicken), Jamioe Bowl (catfish, cheese grits), and Soul Rolls (fried chicken egg rolls). There’s also Kudzu Seafood Company, serving up fresh Gulf seafood and Southern specialties.
For the ultimate in casual, The Rookery’s burgers and soul-satisfying Jimmy Carter shake (peanut butter, bacon) are local favorites. Nu-Way Weiners’ red-hued hot dogs have been pulling crowds since 1916. Craving something sweet? Dovetail’s “cracked pie,” featuring a cookie crust, pecan filling, and salted caramel gelato, is a wonderful Southern specialty.

Fair Winds and Following Seas | Easton, Maryland
With the Chesapeake Bay in its backyard, Easton’s main street is ideal for weekend adventures. Its rich history, well-preserved Colonial and Victorian architecture, stylish boutiques, and award-winning restaurants have made it one of the most appealing small towns in America.
Chef Harley Peet (2024 James Beard Award recipient for Best Chef: Mid-Atlantic) is the maestro behind Bas Rouge, promising exceptional cuisine, wines, and service. Other acclaimed destinations include The Wardroom, an epicurean marketplace during the day, a relaxed yet sophisticated wine and pasta bar at night, and The Stewart, best known for its $1 million collection of rare whiskeys and vintage Champagnes. Alternatively, Tiger Lily, a vibrant and somewhat eclectic tiki bar with an internationally flamboyant menu, and Out of the Fire, an unpretentious destination with a menu emphasizing fresh, locally produced foods, are both hometown favorites.
With so many alluring options, visitors can take in a progressive dinner with drinks at one place and meals at another, for an extravagant and multifaceted experience.
A Taste of History | Bardstown, Kentucky
Established in 1780, Bardstown is recognized as the Bourbon Capital of the World. With nearly 200 buildings on the National Register of Historic Places, a stroll through Bardstown is a passage through time. And although there are plenty of attractions, bourbon is the hallmark of this community.
The Old Talbott Tavern stocks more than 200 bourbons along with an inspired menu. The Bar at Willett, part of the longstanding Willett Distillery estate, offers vintage whiskeys and innovative small plates, including “the best egg salad sandwich ever.”
For exemplary regional cooking, Mammy’s Kitchen & Bar is the place. Their iconic hot brown, adapted for breakfast, lunch, and dinner, is an essential place to start, but you’ll probably want to return for a Kentucky Cornbread Mafia Burger as well.
Should you prefer travel by rail, My Old Kentucky Dinner Train serves gourmet meals while you wind through bourbon country in the comfort of their beautifully restored 1940s vintage dining cars.

A Different Kind of Thrill | Park Avenue District, Orlando, Florida
The stylish Park Avenue District in Orlando’s Winter Park neighborhood, renowned for its public artworks, distinctive shopping experiences, and edifying museums that surround the town’s verdant Central Park, offers considerably more than its theme park neighbors to the south. The visually distinctive Craftsman-style Winter Park rail station at the park, served by Amtrak and SunRail, makes a visit as easy as stepping off the carriage.
Start by visiting The Morse Museum, housing the world’s most comprehensive collection of works by Louis Tiffany. Alternatively, the Scenic Boat Tour through local lakes and narrow manmade canals is an enjoyable pastime.
The neighborhood is also home to an impressive selection of fashionable cafés, bakeries and restaurants. A meal at Prato, led by James Beard-nominated chef Brandon McGlamery, immerses you in refined Italian gastronomy. Coupled with sophisticated decor, Prato mirrors everything that’s wonderful about this community.
If you’d like something more bespoke, Ômo by Jônt is an uncommon experience. Meals are served as a progressive tasting menu limited to 16 guests, with each course enjoyed in a different room.
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