What began as a little friendly competition has grown into something much more meaningful.
After Fredericksburg, Virginia, and DeLand, Florida, found themselves competing for the title of “Best Main Street in the South,” leaders from both communities decided the real victory was not winning a contest. It was creating an opportunity to learn from one another.
Mayor Kerry Devine and Fredericksburg Main Street Executive Director Chris Allen traveled to DeLand July 23–25, 2026, for a visit centered on collaboration, community and celebrating the unique character of two nationally recognized Main Street communities.
Experiencing the best of DeLand
Over three days, the Fredericksburg delegation explored the places, people and traditions that make DeLand a vibrant destination while sharing ideas about the programs, partnerships and events that have helped shape downtown Fredericksburg.
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The visit began with breakfast at the historic Old Spanish Sugar Mill Grill & Griddle House inside De Leon Springs State Park, followed by a scenic boat tour through the spring-fed waters. Along the way, Mayor Devine and Chris Allen enjoyed one of the area’s most beloved attractions — a manatee swimming in its natural habitat.
For Fredericksburg, otters have become a favorite symbol along the Rappahannock River. In DeLand, that same affection belongs to manatees. Seeing one in the wild offered a fun reminder that every community has its own unique treasures and the wildlife that locals proudly call their own.
Celebrating award-winning Main Streets
One of the highlights of the trip was Friday evening’s ceremonial exchange at Pioneer Park.
Community members gathered as leaders from Fredericksburg and DeLand celebrated the friendship that had grown from their friendly rivalry. The ceremony symbolized something larger than a contest. It represented two communities committed to preserving historic downtowns, supporting local businesses and creating memorable experiences for residents and visitors alike.
Community at the heart of it all
Saturday morning provided another memorable experience as the Fredericksburg delegation attended DeLand’s 16th Annual Mayor’s Backpack Giveaway at Earl Brown Park.
Watching hundreds of local students and families come together for the annual event reinforced a common thread shared by both communities: Successful downtowns are built on strong community connections.
Looking ahead
While the contest may have introduced Fredericksburg and DeLand to one another, the relationships built during this visit are what will have the greatest lasting impact.
The exchange provided an opportunity to share ideas, celebrate successes and discover new approaches that can benefit both communities for years to come. It also served as a reminder that some of the best ideas come from connecting with others who are passionate about preserving the character and vitality of their downtowns.
As both communities continue investing in their award-winning Main Streets, the connections formed during this visit lay the foundation for future collaboration, shared inspiration and perhaps a few more friendly competitions along the way.
Sometimes the best prize is not a trophy. It is a new partnership. And while we made some wonderful new friends in DeLand, we have to admit, it still feels pretty good to be able to call Fredericksburg the Best Main Street in the South, as voted by Garden & Gun readers.
