For our fifteenth annual March Madness-style bracket challenge, Garden & Gun took the big dance to the streets to crown the region’s best small-town main drag. After three weeks and hundreds of thousands of votes cast, it came down to Fredericksburg, Virginia’s Caroline Street vs. DeLand, Florida’s Woodland Boulevard. On April 7, as the 11:59 p.m. voting deadline loomed, G&G editors were continuously refreshing results as the contest remained too close to call. In the end, Fredericksburg eked out the victory in our most hotly contested final matchup ever.

A downtown main street
Photo: Fredericksburg Main Street Fredericksburg, Virginia’s Caroline Street.
In an impressive show of local pride, both Fredericksburg and DeLand brought the battle to social media, with local shops and organizations rallying people to vote right up until the last second. “It was truly a shared effort across the whole community,” says Fredericksburg mayor Kerry Devine. “In fact, during Sunday’s watch party—cheering on our University of Mary Washington Eagles, as they won the Division III basketball National Championship—we had the packed house vote during halftime. And did the same during the season opener at the FredNats (our minor league baseball team) and voted during the seventh-inning stretch. We are incredibly proud of our community, and I think this really shows just how much we love it here.

While Caroline Street is the historical and cultural epicenter of Fredericksburg, it hasn’t always been the walkable, charming downtown stretch it is today. In the 1980s the main street was largely big-box stores. But when a nearby mall opened, those chains ditched downtown. “This created an opportunity for many entrepreneurial businesses to move into downtown, and these independent shopkeepers have brought their creativity downtown with them,” Devine says. Beloved tenants of Caroline Street now include Riverby Books and Sammy T’s, a corner pub in an early-1800s building that once served as an auction house and the town’s post office. (Fredericksburg bears the distinction of being George Washington’s boyhood home and the place where James Monroe practiced law.) Likewise, runner-up Woodland Boulevard in DeLand, Florida—which knocked out Paducah, Kentucky, to reach the Championship match—has evolved over time (locals recall the days of Woolworth’s in the 1960s) to become the re-energized, creative stretch of shops it is today. “The heart of our city is more than just the buildings and streets. It is also the people that fill them,” says Deland mayor Chris Cloudman. “The spirit of community pride, service to others, and love for everything that makes DeLand special is shared by fifth-generation residents and new arrivals alike.” No matter the time of year, when you visit this tree-lined passage through the heart of the city, you’re likely to stumble upon a community event—whether it’s a 5K, Mardi Gras dog parade, arts festival, or Santa skydiving into downtown. “There is always an opportunity to join several thousand neighbors in celebration of what makes DeLand…DeLand.” Congratulations to Fredericksburg and DeLand, and all of their passionate residents and fans, for an impressive show of local pride. Thank you to everyone who voted in the bracket.