by | December 1, 2025
Day-Tripping in DeLand
Spend a weekend in this indie-meets-friendly small town.
Prior to becoming a “main street” community focused on preserving its walkable downtown and historic buildings 40 years ago, DeLand was once derisively nicknamed “Deadland”—a place thought to have seen its best days. But by 1997, the National Trust for Historic Preservation gave DeLand its Great American Main Street Award. Today, this small city of around 50,000 people is buzzing with energy, boasting one of Florida’s most charming downtowns—complete with a lively dining scene, public art installations and a modern mom-and-pop vibe. DeLand is best explored on foot, so here are some can’t-miss stops in what just might be Florida’s coolest small town.
DeLand grew up around Stetson University, founded in 1883 by the town’s namesake and baking soda magnate, Henry DeLand. The picturesque campus on the edge of downtown features historic buildings such as Stetson Mansion and a striking statue of John B. Stetson—inventor of the iconic cowboy hat and the man who rescued the school financially after Henry DeLand suffered tremendous financial loss as a result of citrus freezes in the 1890s.
Stroll south along Woodland Boulevard, the city’s main drag, and stop in at Pat and Toni’s Sweet Things for free samples of old-fashioned candy. On the same block, Santorini Greek Cuisine serves what many locals swear are the best gyros and tzatziki in Florida. Book lovers will enjoy browsing The Muse Book Shop and Cliff’s Books; music fans can dig through vinyl at Groovy Records and Steve’s Downtown Music. Don’t miss Nest, a cafe with gifts and home decor; Sidecar Market & Bar, an atmospheric cafe bar that sells craft drinks and furniture; and Pretty Little Things of DeLand, a charming boutique for vintage fashion and furnishings.
Once called Persimmon Hollow, Henry DeLand envisioned the area as a city of the arts. That spirit lives on at the stunning Italian Renaissance–style Athens Theatre. Having hosted concerts and plays since 1921, the theater often lets curious visitors step inside for a peek. The Museum of Art–DeLand showcases an excellent contemporary collection, while downtown DeLand features a historic mural walk and sculpture walk. Stop by the West Volusia Tourism Bureau Visitor Center for guides.
On Friday nights, head to the lively Artisan Alley Farmers Market, featuring fresh produce, local artisans and food stands from local vendors. The alley is closed to traffic and allows open containers, giving the market a festive, street-party vibe. Around the corner on Georgia Avenue, you’ll find the Scottish-inspired Hyderhead Brewery and Trilogy Coffee Roasting Co., serving single-origin, artisan-roasted coffee.
For a main-street stay, book a room at The Historic Artisan Downtown Hotel, a 1924 Spanish Colonial building that once housed the DeLand Hotel. Grab a meal inside at Chicas Cuban Cafe for authentic Cuban dishes and pastries. Finally, cap your evening off at Cafe DaVinci, DeLand’s most happening open-air bar and music venue.
