Beyond the Contest: Fredericksburg and DeLand Share Main Street Successes

What began as a little friendly competition has grown into something much more meaningful.

After Fredericksburg, Virginia, and DeLand, Florida, found themselves competing for Garden & Gun’s title of “Best Main Street in the South,” leaders from both communities recognized that the greatest value wasn’t in winning a contest it was in creating an opportunity to learn from one another.

From July 23–25, 2026, Mayor Kerry Devine and Fredericksburg Main Street Executive Director Chris Allen traveled to DeLand for a three-day visit focused on downtown revitalization, community engagement, and the unique qualities that make each Main Street a destination.

Throughout the visit, the Fredericksburg delegation explored the businesses, attractions, and traditions that contribute to DeLand’s vibrant downtown while sharing ideas about the partnerships, programs, events, and initiatives that have helped shape Downtown Fredericksburg.

The visit began at De Leon Springs State Park, where Mayor Devine and Allen enjoyed breakfast at the historic Old Spanish Sugar Mill Grill & Griddle House before taking a scenic boat tour through the spring-fed waters. Along the way, they experienced one of the area’s most cherished attractions a manatee swimming in its natural habitat. Just as otters have become a beloved symbol along the Rappahannock River, manatees are a source of local pride in DeLand, serving as a reminder that every community has its own unique character and traditions.

The trip also included a community gathering at Pioneer Park, where residents and local leaders celebrated the connection that had grown from the friendly rivalry. Rather than focusing on the outcome of a contest, the event highlighted the shared commitment both communities have to supporting small businesses, preserving historic downtowns, and creating welcoming places for residents and visitors.

On Saturday morning, the Fredericksburg delegation attended DeLand’s 16th Annual Mayor’s Backpack Giveaway, where hundreds of students, families, volunteers, and community organizations came together to prepare children for the upcoming school year. The event reinforced an important lesson shared by both cities: thriving downtowns are built on strong community connections and a shared commitment to investing in people.

The visit provided an opportunity to exchange ideas, celebrate successful downtown initiatives, and explore new approaches that can strengthen both communities. Economic development is driven not only by investment and infrastructure, but also by relationships, collaboration, and a willingness to learn from communities facing similar opportunities and challenges.

Fredericksburg is grateful for the warm hospitality extended by the City of DeLand and looks forward to continuing the relationships established during the visit. While Garden & Gun readers named Fredericksburg the Best Main Street in the South, the greatest takeaway was discovering that some of the best ideas and lasting friendships begin with a little friendly competition.