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  • Northern Virginia Town Wins ‘Best Main Street in the South’ Competition
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Northern Virginia Town Wins ‘Best Main Street in the South’ Competition

The town won the 15th annual ‘Garden & Gun’ competition, which included 16 competitors.

By Debbie Williams April 9, 2026 at 10:46 am

Historic Fredericksburg has something brand new to brag about. Caroline Street won Garden & Gun’s 15th annual competition for the Best Main Street in the South.

Fredericksburg bested several competitors in the March Madness–style bracket competition. Voters chose the area over Eureka Springs, Arkansas; Bristol, Tennessee; and Blowing Rock, North Carolina.

The final round pitted Caroline Street against Woodland Boulevard in DeLand, Florida.

The three-week competition had hundreds of thousands of votes, Garden & Gun reported. “Fredericksburg and DeLand brought the battle to social media, with local shops and organizations rallying people to vote right up until the last second,” according to the publication.

“It was truly a shared effort across the whole community,” Fredericksburg mayor Kerry Devine told Garden & Gun. “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.”

Some of the businesses along Caroline Street include sci-fi inspired cookie shop Smugglers Cafe; children’s toy store Jabberwocky; rare book seller Riverby Books; and casual eatery Sammy T’s.

Feature image, stock.adobe.com

Debbie Williams

Debbie Williams

Senior Editor

Northern Virginia Magazine Senior Editor Debbie Williams is a George Mason University graduate and longtime NoVA resident. She has more than 20 years of experience writing and editing for a variety of nonprofit, lifestyle, and government publications, including for AARP.org and USA TODAY magazines.

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