The Bracket Rivals Who Became Main Street Pen Pals

The Final That Felt Like a Tie

The annual bracket that pits sixteen of the South's best main streets against each other reached a final that still feels close. Caroline Street in Fredericksburg, Virginia, faced Woodland Boulevard in DeLand, Florida, in a head-to-head that came down to the narrowest margin in the contest's history. When the online voting closed, Fredericksburg had taken the title, but DeLand held its head high, and the two towns traded congratulations that felt more like mutual recognition than concession. The friendship that followed wasn't orchestrated. Fredericksburg's mayor, Kerry Devine, was already heading to Florida to visit family and noticed she'd be staying near DeLand. She floated the idea of a quiet drop-by to Chris Allen, the city's main street planner. He declared he'd come along, emails flew, and DeLand's crew—led by main street director Stephanie Mullins—jumped into planning a welcome.

A Day of Pancakes and Manatees

The welcome Devine and Allen received was warm, hands-on, and thoroughly DeLand. Their itinerary opened with a make-your-own pancake breakfast at Sugar Mill, where both guests flipped their own cakes on the griddle. From there, a boat ride at De Leon Springs State Park drifted past manatees in the clear spring run—a species that would later become a token of the friendship. The rest of the day was given over to wandering downtown, poking into shops, and talking with local business owners. Mullins, who helped set the schedule, says the town was proud to show off what it has built. For Devine, the visit answered a question she had carried since the bracket: why so many people love DeLand. The answer, she'd later say, was visible in the details—the window displays, the lack of empty storefronts, the way people stopped to chat.

Two Towns, Same To-Do List

Once the pleasantries were done, Devine and Allen got down to the real business of comparing notes. Both towns are home to universities, both have historic centers, and both run mural and public sculpture programs. The conversation turned to the nitty-gritty of downtown upkeep: what business hours actually work, which community programs draw families out, and how to find new uses for historic buildings like the old courthouses that anchor both main streets. Stephanie Mullins summed up the shared challenge: "We are both balancing growth with staying true to who we are." The dialogue wasn't a competition; it was a workshop. For two planners who spend their days solving the same puzzles, the exchange was as practical as it was friendly.

From Dead Land to Destination

The shared history goes deeper than current charm. Before each town underwent its main street revival, DeLand was known locally as "Dead Land" and Fredericksburg as "Dead Fred" because both were empty of visitors and businesses. Mullins had a good laugh over that with the visitors, noting how rewarding it is to see years of community engagement paying off. Residents are now so proud of their downtowns that they'll vote in an online bracket until their fingers go numb. The transformation didn't come from a single project or a sudden grant. It was the slow accumulation of small, deliberate moves—storefront renovations, event programming, pedestrian-friendly tweaks—that turned two dying streets into places people refuse to lose.

Keys, Mascots, and a Return Invitation

To make the friendship official, the mayors exchanged keys to their cities, a ceremony made lighter by a second trade: stuffed animals representing each town's mascot. Fredericksburg offered a river otter; DeLand countered with a manatee—the same creature that had surfaced in the springs earlier that day. The visit closed with talk of a return trip, and DeLand's representatives are already planning to head north. "Of course, we'd love to host DeLand in return," Devine said. "These days, it's so important to remember how much we all have in common, and we definitely came away from this visit with that." She added that the two towns should learn from each other rather than compete. The bracket may have produced a winner, but the partnership looks like the real prize.