Fredericksburg’s downtown is charming, rich in historical significance, home to a vibrant small-business community and the rest of the South is taking notice. This year, in its 15th annual regional competition, Garden & Gun named Downtown Fredericksburg’s Caroline Street the Best Main Street in the South.
The bracket-style competition featured 16 main streets from across the South, with hundreds of thousands of public votes cast over the course of three weeks to determine the winner. The competition was a close call, with voting happening up until the last minute and Woodland Boulevard in DeLand, Florida taking second place.
City officials heavily promoted the competition, local businesses put out repeated calls for participation and residents rallied one another, leading to Fredericksburg taking the win, reflecting the community’s spirit and commitment to our city.
Over the years, downtown Fredericksburg has grown into a vibrant district that blends history with modern tastes. Its historic roots can still be seen in colonial-era buildings, museums and landmarks.
Visit the Fredericksburg Area Museum, the James Monroe Museum and Memorial Library or Historic Kenmore, where George Washington’s sister, Betty Washington Lewis, and her husband, Fielding Lewis, lived. Other historic sites include the Hugh Mercer Apothecary Shop and the Mary Washington House, where George Washington’s mother, Mary Ball Washington, spent the last 17 years of her life.
Complementing downtown Fredericksburg’s historical sites are the numerous modern art galleries, restaurants, boutiques, coffee shops, bakeries, antique shops and bookstores. On Caroline Street, alone, a family can shop for literary finds at Riverby Books, discover artwork and handmade goods from regional artists at PONSHOP and enjoy authentic Italian food at Orofino.
Downtown Fredericksburg is also home to many unique businesses that you would be hard-pressed to find elsewhere. Not many cities can boast that they have a shop like Possum-bilities, where you can purchase nature-related gifts while attending storytime with an opossum, or Smugglers Cafe, an immersive sci-fi cafe with freshly baked, half-pound cookies.
The downtown area is also known for its proximity to the Rappahannock River with many parks and walking trails nearby, trolley rides and an active farmer’s market. Locals have come to love and expect annual activities like sidewalk sales, First Fridays, Scarecrow Fest, Window Wonderland and the Annual Christmas Parade.
With its extensive history, unique small businesses and lively events, the downtown area is an integral part of Fredericksburg. With this new and well-deserved title of Best Main Street in the South, the city joins a growing list of Southern destinations receiving national attention for their history, character and community charm; just some of the many reasons we love to call Fredericksburg home.
FredParent is your go-to resource for raising a family in the ’Burg. Whether you’re making smart money moves, celebrating local wins like Caroline Street earning national recognition, or diving into our much-anticipated 12th Annual Family Favorites issue, we’ve got you covered. Plus, find tips for traveling abroad with kids and what to know before you go, explore our helpful guide to pools and splash pads around Fredericksburg this summer, and take a closer look at a flexible, college-prep online high school option for your gifted student. From everyday moments to memory-making milestones, it’s all here.
