Fredericksburg Parent

18 Fredericksburg Parent and Family • August 2026 Fredericksburg may have been crowned "Best Main Street in America" by Garden & Gun magazine's 15th annual competition in April 2026, but the runner-up is well worth a road trip of its own. DeLand, Florida, a quaint town about 40 miles north of Orlando, took the number two spot in this year's main street competition, and its very own Woodland Boulevard has plenty to offer families. Whether you make it a standalone getaway or tack it onto a Disney trip, here's what you'll find along DeLand's charming main street. Culture DeLand is home to Stetson University, whose historic campus sits on the edge of downtown. Among its most striking buildings is Stetson Mansion, named for John B. Stetson, the phi- lanthropist and inventor of the cowboy hat. Tours of the three-story home and its grounds are available year-round, and the mansion is a popular destination at Christmastime. Families can catch a concert or play at Athens Theatre, an Italian Renaissance-style venue that has hosted musical and theatrical performances since 1922. Art lovers can explore the galler- ies lining DeLand's main street corridor, along with the DeLand Historic Mural Walk, which features more than a dozen outdoor murals throughout the historic downtown. On Friday evenings, Artisan Alley Farmers Market is the place to be. The street closes to vehicles, creating a festive, pedestrian-friendly atmosphere with local food vendors, artisans and live entertainment. Artisan Alley is a gath- ering space in the heart of downtown DeLand with a restaurant, a brewery, a butterfly garden and more. Shopping and Dining Woodland Boulevard is lined with mom-and- pop gift shops and boutiques perfect for window-shopping or finding a one-of-a-kind souvenir. Book enthusiasts can browse Cliff's Books or Muse Book Shop, while music lov- ers should head to Groovy Records or Steve's Downtown Music. Other standout storefronts include Empire's Emporium, a men's clothing store; Pretty Little Things of DeLand, which specializes in vintage fashion and home décor; the pet boutique Gurrs & Purrs; DeLand Asian Market; and Marketplace at Rivertown, an antiques shop selling antiques and nostalgic collectibles with rotating inventory for a unique shopping experience. Hungry families won't struggle to find something to eat while there. Downtown DeLand offers everything from Asian and Mexican cuisine to sandwich shops and pizza joints. Locals rave about the gyros and tzatziki at Santorini Greek Cuisine, and no visit is complete without a stop at Pat and Toni's Sweet Things for chocolate, pralines and fudge. For something cold and sweet, try BerryVille DeLand or Whit's Frozen Custard. Beyond Main Street DeLand has plenty to offer past its downtown core, too. Lake Beresford Park features hiking and biking trails, playgrounds and picnic pavilions, while Bill Dreggors Park includes a playground and a sensory butterfly garden. The Reptile Discovery Center houses more than 100 reptiles and offers interactive programs, while history buffs can explore Stetson University's Gillespie Museum, dedicated to earth science. However, the museum is only open for tours during the academic year, so be sure to check current hours before your visit. Families with extra time should consider a trip to Hontoon Island State Park. Accessible only by public ferry or private boat, the park offers a playground, picnic area and nature trails, along with fishing, canoeing and kayaking for those who want to spend the day on the water. Where to Stay For a true main-street experience, book a room at The Historic Artisan Downtown Hotel, right in the heart of downtown. Chain hotels and vacation rentals are also available nearby, and for those who enjoy the great outdoors, Hontoon Island State Park offers incredible camping options. Why DeLand Is Worth the Drive With its historic architecture, walkable downtown and vibrant mix of culture, food and nature, it's no wonder DeLand was a close contender in this year's "Best Main Street in the South" competi- tion. Well done, DeLand. You continue to prove that some of Florida's best family memories are made off the beaten path. For more information, visit mainstreetdeland.org. DeLand, Florida WRITTEN BY BRANDY CENTOLANZA Takes Its Turn in the Spotlight Small-Town Charm Stetson Mansion Athens Theatre Hontoon Island State Park

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