Athens Theatre, which dates to 1921, is one of the few existing examples of a classic American theater in Central Florida.

DeLand

DeLand is the “Mayberry” of Central Florida cities, with a downtown seemingly stuck in time, with older architecture dating back to the 1920s. 

Sure, they have a chocolatier with old-fashioned goodies, a one-off donut shop that opens at 5:00 a.m. without fail and even boasts parades for Christmas, 4th of July, Veterans Day and Memorial Day, but that is where the “Mayberry” comparison ends.

Underneath its somewhat sleepy exterior, this city has a lot of meat to it. Take Bake Chop, known for their amazingly fresh sandwiches and sides; their space in Artisan Alley has single and shared tables, so don’t be surprised if you’re seated next to a friendly neighbor. Have a chat … you may like what you hear. Down the street you’ll find Persimmon Hollow Brewing Co., a popular local brewery offering a fun, relaxed environment for everyone, even families and well-behaved pups. For a refreshing summer brew, try the Daytona Dirty Blonde, a blonde ale that is light, crisp and perfect for a hot Florida day. Across the alley, you’ll find Café DaVinci, the city’s premier outdoor music venue. Set against the backdrop of a majestic oak tree wrapped in twinkling lights, it’s a great spot to catch a local band or a traveling one. Head back to the main street and pop into Urban Brick, a family-owned Italian restaurant with some unusual menu items you won’t see elsewhere. 

The Architecture 

Take a walk down North Florida Avenue and there you’ll find the Athens Theatre, one of the few existing examples of a classic American theater in Central Florida. Once the centerpiece of DeLand, the Athens Theatre is a jewel of Italian Renaissance architecture. This historic theater was designed in 1921 by prominent Orlando architect Murray S. King. On Woodland Boulevard, you can spot the Artisan Inn, the original DeLand Hotel in the late 1920s, later renamed the Landmark Hotel. A short stroll or drive down Woodland will take you into the heart of Stetson University. Built in 1884 as the campus’ first building, DeLand Hall was restored in 1981, and placed on the National Register of Historic Places in 1983. It was restored again in 2002. Wanting a peek inside a home of the past? Take a tour of Florida’s First Luxury Estate, built in 1886 for famed hat maker John B. Stetson. It is the largest, grandest and most historic home ever built in Florida before the 20th century. Stetson is often referred to as Florida’s first snowbird and was a famous hat baron. The home has been restored and updated in a timeless fashion. Historic tours are offered between February and September.

On Woodland Avenue, you’ll find Pat & Toni’s Sweet Things, where Elizabeth O’Hara, Sofia Boza and Tanya Bustamante (below) showcase award-winning treats.

A Little More About the Food

Is your mind drifting back to thoughts of the local chocolatier? A trip to Pat and Toni’s Sweet Things is a must. Set in the heart of historic downtown on Woodland, Pat and Toni’s does things the old-fashioned way. As you enter the store, their fudge selection is on full display. To the right, their chocolate counters are filled to the brim with everything imaginable you could dip in chocolate; potato chips, Oreos, pretzels, peanut butter cups and more. What really makes them a standout is their selection of truffles and chocolate-covered fruit. Get the kiwi and the orange slices; you’ll thank us later. DeLand is not without its fancy spots too. Cress Restaurant is a great example, which is celebrating 16 years in downtown DeLand in August. Owned by Tom and Suran Brandt, this husband-and-wife-led restaurant serves up a feast for the eyes and stomach with amazingly thoughtful, locally sourced dishes.  

Downtown DeLand beckons with the Persimmon Hollow Brewing Co. on west Georgia Avenue.

Specialty Shops Abound

DeLand’s historic main street has more to offer than just great restaurants; shops are more eclectic, often with the same owners for decades. Take Cliff’s Books, an unassuming storefront tucked into Woodland’s main street. Since 1983, Cliff’s Books has been the go-to source for books, comics and all things collectable in downtown DeLand. 

Warehouses on DeLand’s west Georgia Avenue have been converted into restaurants, retail and a craft brewery.

Annual Events 

The city’s main street hosts regular events throughout the year. Every Friday night, vendors post up to sell their goods in Artisan Alley, while Persimmon Hollow Brewing supplies homegrown beers brewed in-house and board games for those who need a little more distraction (or fun)! The weekly farmers market happens every Friday evening from 6–9 p.m. Bigger annual events include the DeLand Ice Cream Walk (a great summer kick-off), a craft fair in the fall, a craft beer festival in the spring and several other amazing events that bring in people from all around Florida, and beyond.

 The neighborhoods surrounding DeLand’s main street are equally pretty. You’ll see fewer cul-de-sacs and curvy roads and more intersecting grids, making getting in and out of the neighborhood fairly easy. Home styles range from large Victorian-style homes with welcoming front porches to wood frame vernacular style homes, more commonly known as cracker architecture. You may spot a few Tudor revivals or even prairie style homes in the area. Whatever you choose, you’re bound to enjoy this small-town vibe. 

Main Street Orlando