click to enlarge persimmonhollow3_jby.jpg

Wandering through historic DeLand is a day well spent 

It’s a college town – home to Stetson University – with a historic downtown bustling with people of all ages. You may feel as though you’ve stepped into Stars Hollow when you realize how tight-knit the community is, but don’t worry, they like strangers too. So feel free to wander among the restored old buildings repurposed into shops, restaurants, brewpubs, wine bars and artisanal food purveyors. If you overindulge, you can always book a room at the Artisan Downtown boutique hotel – unless it’s Game Day or Parents’ Weekend at the college.

Cress Restaurant

103 W. Indiana Ave., DeLand, 386-734-3740,

Also known as "the reason a lot of Orlandoans drive to DeLand." Hari and Jeneffer Pulapaka serve pristine prix-fixe tasting menus with perfectly paired wines, and use only local and sustainable ingredients.

South of NY Market

100 S. Woodland Blvd., DeLand, 386-279-7630,

Finally, someone combined shopping with wine. Shop or grab a spot at the bar in this vintage market that mixes modern elements with retro style all the way down to their penny-tiled floors.

Trilogy Coffee Roasting Co.

136 W. Georgia Ave., DeLand, 386-624-6057,

Enjoy your caffeine fix in DeLand's newest coffeehouse in a clean, neutral aesthetic with pops of greenery. You'll also find goods by local businesses for sale in the café.

Café DaVinci

112 W. Georgia Ave., DeLand, 386-736-0008,

The character-rich live music venue offers indoor and outdoor stages, plus a charming – and huge – courtyard bar area. Booking is eclectic; keep an eye on their calendar.

Persimmon Hollow Brewing Co.

111 W. Georgia Ave., DeLand, 386-873-7350,

It would be harder to think of reasons not to drink at Persimmon Hollow than to list all the reasons you should – but the pros include the historic building, the stellar beers brewed in-house, and the close proximity to Neighbors Artisan Taqueria.

Neighbors Artisan Taqueria

112 W. Georgia Ave., DeLand, 386-279-0394,

Snuggled into an elbow of the Café DaVinci courtyard, Neighbors serves up tacos from tame to adventurous plus house-made guac, queso and salsa.

DeLand Wings

100 block of South Woodland Boulevard, DeLand,

Painted by a local DeLand artist, these wings are appropriately found in Artisan Alley. With almost 2,700 #DelandWings posts on Instagram, you won't be able to resist adding your own.

We welcome readers to submit letters regarding articles and content in Orlando Weekly. Letters should be a minimum of 150 words, refer to content that has appeared on Orlando Weekly, and must include the writer's full name, address, and phone number for verification purposes. No attachments will be considered. Writers of letters selected for publication will be notified via email. Letters may be edited and shortened for space.

Email us at

Orlando Weekly works for you, and your support is essential.

Our small but mighty local team works tirelessly to bring you high-quality, uncensored news and cultural coverage of Central Florida.

Unlike many newspapers, ours is free – and we'd like to keep it that way, because we believe, now more than ever, everyone deserves access to accurate, independent coverage of their community.

Whether it's a one-time acknowledgement of this article or an ongoing pledge, your support helps keep Orlando’s true free press free.

More in Annual Manual


Never miss a beat

Sign Up Now

Subscribe now to get the latest news delivered right to your inbox.

Read the Digital Print Issue

February 24, 2021

View more issues


© 2021 Orlando Weekly

Website powered by Foundation