Caroline Street has danced its way all the way to the finals of Garden & Gun magazine’s “Best Main Street in the South” showdown, and it’s time to turn up the volume on those voting fingers.
In a March Madness-style bracket that’s had the whole South buzzing since mid-March, Fredericksburg’s historic downtown drag finds itself in the ultimate two-street final against Woodland Boulevard in DeLand, Florida.
Public voting for the championship round is underway now and runs through Thursday, April 7, at 11:59 p.m. The winner will be announced on Wednesday, April 8.
It’s been quite the run. Garden & Gun’s selection committee started with a Sweet 16 of standout Southern main streets chosen for their community feel, independent businesses (no cookie-cutter chains here), historic character, walkability, events, and that unmistakable local vibe that makes you want to linger. Public voting kicked off March 17, with rounds rolling roughly weekly.
Along the way, some serious contenders fell by the wayside: the mountain charm of Blowing Rock, North Carolina; the creative energy of Paducah, Kentucky’s Broadway; the split-personality appeal of Bristol on the Virginia-Tennessee line; and the historic warmth of Shepherdstown, West Virginia’s German Street, among others. But Caroline Street? It kept showing up, powered by overwhelming local love and relentless cheering from residents, visitors, and small-business owners.
“This is an incredible moment for Downtown Fredericksburg,” said Chris Allen, Executive Director of Fredericksburg Main Street. “This recognition is a direct reflection of our small businesses, our vibrant downtown experiences, and a community that continues to show up and support one another.”
The nonprofit Fredericksburg Main Street has been firing on all cylinders with a press release, social media blitz, and in-store signage urging everyone to vote early and often. The pitch is simple: Caroline Street’s brick-lined blocks capture everything special about Fredericksburg—its layered history, independent shops and restaurants, lively parades and farmers markets, and that warm, walkable energy that makes downtown feel like home.
Voting couldn’t be easier. Head to the Garden & Gun bracket page. No account needed, no personal info required. You can vote once per hour per device. Takes less than 10 seconds. Every single vote counts in what’s shaping up to be a nail-biter.
Now, let’s talk about the two finalists in this friendly Southern showdown—because both streets bring serious flavor, just in very different ways.
Caroline Street in Fredericksburg, Virginia, is pure time-travel magic with a modern heartbeat. Tucked in a town just an hour south of Washington, D.C., this colonial and Civil War-era gem sits within a 40-block National Historic District. Stroll its brick sidewalks and you’ll find zero chain stores—only independent gems like Riverby Books for your next great read and Sammy T’s, a cozy corner pub tucked inside an early-1800s building that once served as the post office and an auction house. It’s the kind of place where chef-owned restaurants, craft breweries, antiques shops, and boutiques spill out onto the street during festivals, First Fridays, parades, and the weekly farmers market.
The vibe? Proudly historic but never stuffy. You can feel the echoes of George Washington’s boyhood nearby (his birthplace and several battlefields are a short drive away), yet the energy today is all about community gathering. It’s walkable, welcoming, and unapologetically local—exactly the kind of main street that makes you slow down, chat with neighbors, and leave with a full belly and a lighter wallet in the best possible way.
Woodland Boulevard in DeLand, Florida, brings a whole different kind of sunshine to the party. This palm-lined thoroughfare is the creative heart of Central Florida’s DeLand, blending Victorian storefronts with a youthful, artsy edge thanks to its proximity to Stetson University.
Think vibrant murals, the DeLand Sculpture Walk, a Historic Mural Walk, galleries, boutiques, cafes, and bookstores. Live music drifts from venues, farm-to-table spots highlight local flavors, and outdoor art festivals keep the calendar packed. It’s got that relaxed “Old Florida” charm with nearby natural springs and beaches just a short hop away. DeLand’s downtown previously earned Great American Main Street recognition, and its creative, sun-dappled vibe offers a laid-back cultural counterpoint to more traditional Southern streets.
Side by side: Fredericksburg delivers deep-rooted American history, brick-and-mortar stories from the 1700s and 1800s, and that classic Virginia small-town pride wrapped in parades and patriotism. DeLand counters with artistic flair, palm trees swaying overhead, and a bohemian creativity that feels like a breezy Florida embrace.
“We’re one step away from bringing this title home,” Allen added. “This is where every vote truly matters. We’re asking everyone to take a few seconds, cast their vote, and continue showing up for Downtown Fredericksburg.”
