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.
103 W. Indiana Ave., DeLand, 386-734-3740, cressrestaurant.com
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, facebook.com/southofnewyorkmarket
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, trilogycoffee.com
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.
112 W. Georgia Ave., DeLand, 386-736-0008, cafedavincideland.com
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, persimmonhollowbrewing.com
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, neighborsdeland.com
Snuggled into an elbow of the Café DaVinci courtyard, Neighbors serves up tacos from tame to adventurous plus house-made guac, queso and salsa.
100 block of South Woodland Boulevard, DeLand, facebook.com/delandwings
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.