Driveable Destinations: DeLand

This Main Street America town offers a glimpse at its past as it celebrates its future.

This hidden gem in Volusia County has been voted Best Main Street in Florida five times and its quaint, historic downtown is ideal for a day trip.

Just a short, scenic drive across the Ocala National Forest takes you to the charming small town that founder Henry DeLand envisioned as the educational and cultural mecca he called “the Athens of Florida.” With wide, pedestrian-friendly sidewalks and artworks sprinkled liberally throughout town, this city of around 40,000 residents was one of the first in Florida to receive the Main Street America designation nearly 40 years ago. 

About 60 miles from Ocala, you’ll find DeLand’s business district centered around the intersections of state Highway 44, known locally as New York Avenue, and state Highway 17, or Woodland Boulevard. Parking is free at several lots within a few blocks.

History and Higher Education

Baking soda manufacturer Henry DeLand visited a tiny community then known as Persimmon Hollow in spring 1876 with his brother-in-law, who wanted to grow oranges. The New Yorker fell in love with the rolling pine meadows along the eastern shore of the St. Johns River and purchased his own homestead. When he donated land for a school, church and main thoroughfare a few years later, residents named the town in his honor.

The educational institution that opened in 1883 as DeLand Academy was renamed Stetson University in 1889 after John B. Stetson, the trustee and donor who made his fortune in hats. The private university’s 175-acre campus is designated by the National Register of Historic Places for Florida’s oldest collection of education-related buildings, including DeLand Hall, the oldest building in Florida in continuous use in higher education, and Sampson Hall, opened in 1908 as a Carnegie library.

Photo courtesy of Main Street DeLand Association
Photo courtesy of Main Street DeLand Association

Now open to visitors for holiday tours in November, December and January, the Stetson Mansion, known as “the house that hats built,” is Florida’s only Gilded Age mansion. When hatmaker Stetson built his innovative, three-story winter retreat in 1886, it had all the modern conveniences: Steam heat, indoor plumbing, electricity—installed by Thomas Alva Edison himself—and a private railway spur, thanks to Henry Flagler. The estate was purchased in 2005 by J.T. Thompson and Michael Solari and, after extensive renovation, they opened their residence to the public for holiday tours. The 10,000-square-foot Victorian manor, with a blend of Gothic, Tudor, Moorish and Polynesian details, features rare parquet wood floors and 10,000 panes of original leaded glass windows. 

The historic Athens Theatre, a jewel of Italian Renaissance architecture, has been restored to look much as it did when it opened in 1922. Now the home of the Athens Theatre Company and Athens Theatre Youth Academy, the venue hosts live plays and music events. 

An Abundance of Art

In downtown DeLand, even parking lots are adorned with art. Lot No. 2, just east of the city center, celebrates the city’s 2019 designation as Florida’s first Monarch City USA with a dozen larger-than-life butterflies on a vibrant blue background. Gazing at them from the lot’s north side is beloved bootblack Rufus Pinkney, on a mural marking the spot where Rufus’ Shoe Shine Parlor stood for nearly 40 years before he passed away in 2016 at age 84.

The city’s website at offers a downloadable guide to the DeLand Sculpture Walk, which features a dozen 3D works curated by the Museum of Art-DeLand. You’ll find 10 DeLand Butterflies throughout downtown, with their translucent wings reflecting brilliant yellow and orange onto the sidewalk, as well as functional art such as the Sunflower Whisper Bench, where you can stop and rest among oversized blooms created from steel and hand-blown glass.

The shady Chess Park at the Courthouse Plaza is a haven for chess players, with permanent chess tables and a life-size chess board, and is a cool respite for anyone, with benches overlooking the mural, A Conversation Over Chess in 1929, and the soothing sound of the water wall fountain.

Don’t forget to look down—the 20 works in the Miniature Art Adventure, a collaboration between the city and the art museum, adorn mundane grates, pipes and steps with colorful and whimsical touches throughout the business district. Thanks to another city-museum collaboration, a dozen utility boxes throughout town are wrapped with original art.   

Photo courtesy of Main Street DeLand Association

Be sure to venture down Artisan Alley, where you’ll find the perfect selfie spot: The Wings, mural, painted in 2014 by local artist Erica Group after wings she chalked onto a door for a dress shop photo shoot went viral and the building owner requested that she paint a permanent version. Farther down the alley, another Group mural, Beer—Grain to Glass charts the Persimmon Hollow Brewing Company’s process along the side of its taproom. Get more details about these and 13 other murals, as well as a downloadable guide to the DeLand Mural Walk, at

Photo courtesy of Main Street DeLand Association
Photo courtesy of Main Street DeLand Association

Stroll, Shop and Sip

The wide sidewalks of Woodland Boulevard were made for strolling and window shopping. North of New York Avenue, stop in Boho Collective, Pinup Parlor and Shellsea for boutique apparel and accessories and distinctly Florida fashions. For artsy gifts and accessories, visit the Museum of DeLand’s expansive museum store and find juried works by more than 30 local artists around the corner at the ArtWorks DeLand co-op gallery on West Indiana Avenue.

Venture south of New York Avenue for vintage finds from clothing to records to home décor. Look for the powder-blue antique Oldsmobile convertible parked in front of Nancy’s Vintage and Retro. Next door, Ms. Preppy Pants offers upscale women’s consignment and another neighbor, Steve’s Downtown Music, sells new and used CDs, records, posters and T-shirts. Continue down the block to the Marketplace at Rivertown, a three-story antique mall. Just don’t pass up the Muse Book Shop, where the local owner has offered bestsellers, Floridiana and fine old, rare and out-of-print books since 1980. Around the corner, Florida Victorian Architectural Salvage, in a restored 8,000-square-foot 1926 building, is packed to the rafters with antique lighting fixtures, doors, windows and miscellaneous building bits.

When you’re ready to wet your whistle, choose from diverse options including craft cocktails, fine wine, fresh microbrews or high tea. The venerable Elusive Grape offers more than 40 wines by the glass as well as wine flights. The eclectic Sidecar Market features a beer, wine and coffee bar and sangria slushies with seating among upcycled furniture, local art and retro décor. Persimmon Hollow Brewing Company, which hearkens back to the area’s original name, pours pints of ales and lagers in the expansive taproom. Both the Tea Room at Destinations and Sweet Tea Café DeLand offer English-style high tea with savories and sweets served on fine china.

Photo courtesy of Main Street DeLand Association

Delightful Bites

If you visit on Saturday or Sunday, don’t be afraid to venture underground for a bottomless brunch—with optional endless mimosas—featuring a Southern-inspired menu of scratch-made small plates such as shrimp and grits and fried chicken plus waffle, omelet and dessert stations. The Table, located at the main intersection, features outdoor seating in a sunny basement courtyard next to the River Life manatee mural fountain.

Photo courtesy of Main Street DeLand Association

In Artisan Alley, BakeChop offers locally sourced, handcrafted sandwiches and salads six days a week. On North Woodland Boulevard, chef and owner Manny Politis serves up authentic Greek and Mediterranean dishes, including gyros, spanakopita and baklava at Santorini Greek Cuisine, open for dinner Tuesday-Thursday and lunch and dinner on Friday and Saturday. On South Woodland Boulevard, Chicas Cuban Café, located in the Artisan Hotel, features authentic island favorites, from traditional Cuban sandwiches to roast mojo pork and picadillo, plus specialty Cuban coffee drinks. Chicas is open for breakfast, lunch and dinner seven days a week.

In the mood for something sweet? At Pat and Toni’s Sweet Things, on North Woodland Boulevard, choose from hand-dipped chocolates or an extreme topped milkshake.

Sky High Adventure

With more than 100,000 skydivers a year, this small town is known as the skydiving capital of the world. Adventurers have been skydiving at the DeLand Municipal Airport since 1959, and more than 600 local residents are employed at 24 parachute equipment manufacturing and other skydiving-related businesses. At one of the country’s busiest drop zones, beginners can take tandem jumps and bona fide adrenaline junkies can take accelerated freefall training and participate in freestyle and free flying competitions.

Not sure you’re ready to take the plunge? Watch the skydivers from the ground from the outdoor deck at the onsite Airport Restaurant and Gin Mill, open for lunch, dinner and happy hour, with live music in the evenings. OS

To learn more, go to

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