Craving a charming escape with your special someone? Look no further than DeLand, Florida! This vibrant town, nestled just a short drive away, offers the perfect blend of historic allure, cultural delights, and romantic charm. Embark on a day trip to DeLand and discover a treasure trove of antique shops, captivating museums, and delightful cafes – all waiting to create unforgettable memories for you and your sweetheart.

Updated March 2024 by Meghan Roth

Downtown DeLand – Things to Do, Dining, and Shopping

PLAY

Highland Park Fish Camp

2640 W. Highland Park Road, DeLand, FL 32720

This rustic hidden gem is located on the Norris Dead River, a portion of the St. Johns River, beside a 23,000 acre preserve. Bring your own boat or rent one to take in the “Old Florida” scenery. The water is loaded with largemouth bass year-round making this an ideal spot for fishing and other outdoorsy fun.

Guided tours are available for novice fishermen. Spend the day or rent a cabin for an overnight wilderness adventure.

Highland Park Fish Camp – Image from Highland Park Fish Camp

Skydive DeLand

1600 Flightline Blvd, DeLand, FL 32724

Thrill seekers can take to the sky to fly from 14,000 feet. Skydive DeLand states, “The method of tandem skydive and the equipment was conceived and developed here in DeLand, Florida.” So that seems to make this place pretty legit!

In fact, because of Skydive DeLand, this small town is recognized as the Skydiving Capital of the World. Newbie divers will take in a bird’s eye view via tandem dive, and well-experienced divers can brave the Accelerated Freefall.

Fellow Earthlings Rage Room

1611 FL-15 Alt, DeLand, FL 32720

Life is full of stressors… and sometimes it’s beneficial to vent out these frustrations. Rage rooms invite adults to break the cycle of tension by breaking all sorts of stuff (plates, bottles, electronics, etc.) – while wearing safety gear within a specialty-furnished room.

If a rage room sounds like the total opposite of romance, well you might be right. But this will certainly create a unique, shared memory!

Wise Axe DeLand

303 N. Woodland Blvd, DeLand, FL 32720

You already hit the bull’s eye when you started dating your love. Now, see who can score the most bull’s-eye points on an axe-throwing date night. The adrenaline rush from throwing an axe and actually making it stick to the wooden target is pretty thrilling. An axe coach will gladly assist you with technique and things to know before letting you bravely take a stab at it.

Also Try:

Dyno Climb – 528 S Woodland Blvd, DeLand, FL 32720
Lake Beresford Park – 2100 Fatio Rd, DeLand, FL 32720
MindQuest Escape Rooms – 207 North Woodland Boulevard, DeLand, FL 32720
Tiny Houseboat Adventures

Downtown DeLand Historic District

The most well-known thing to do in DeLand is the awesome historic district. This main drag exudes a quintessential vibe of historic living. See notable 19th-century buildings, shop quaint boutiques, savor local eateries and more.

Keep reading for the best places to eat and shop in Historic Downtown DeLand.

STROLL & SHOP

Locally, you’ve wandered along Plant Street in Winter Garden, Park Avenue in Winter Park and Main Street in Mount Dora. Similarly, this main drag in DeLand exudes historic living.

The two of you will surely discover one-of-a-kind bookstores, antique vendors, vintage clothing retailers and even groovy record stores. Stroll, shop and nosh the day away.

DeLand Indie Market at Artisan Alley

113 W Georgia Ave DeLand, FL 32720

This curated indoor/outdoor market event is typically held four times a year. It features roughly 70 pop-up boutiques, artists and handcrafted vendors from all over the Sunshine State.

Check their Facebook page for updates.

Orlando Art Markets We Love — Image credit: DeLand Indie Market at Artisan Alley

DeLand Mural Walk

Explore the city with the DeLand Mural Walk as your guide for a masterpiece day trip date.

Click HERE to download the Mural Walk brochure. You’ll be tickled pink exploring the Downtown area through this creative and beautiful experience.

If sculpture is more your thing, check out the DeLand Sculpture Walk. The walk is free and open to the public year-round, so everyone can enjoy these engaging works of art. The sculptures, which are changed out every two years, will be in place until 2025.

DINE

Persimmon Hollow Brewing Company

111 W Georgia Ave, DeLand, FL 32720

You may notice the name of this brewery as it has a Lake Eola location as well. But the DeLand site was pouring out the goodness first. So, the motto of this microbrewery is: “Drink responsibly, but get weird.” Okay, sounds like a plan!

The tap room, opened by two local besties who poured their passions for beer into a business venture, offers a great selection of brews, including core concoctions like the Funky Freddy Fitz (Belgian stout, ABV: 6.5%) and Beach Hippie (IPA, ABV: 7.1%), in addition to limited releases.

Persimmon Hollow Deland – Dani Meyering

Check out the Local Restaurants

Skip chain establishments to get a taste of DeLand’s locally-owned restaurants.

Santorini, authentic Greek grub
De La Vega, modern Latin fusion fare with gluten-free and vegetarian options
Urban Brick, farm-to-table fresh Italian food
The Table DeLand serving breakfast, lunch, dinner & Sunday Brunch
Cook’s, a hearty, homestyle buffet
BakeChop, an artisan kitchen with serious dessert skills
DeLand Fish House, offering all-u-can-eat shrimp and more.

Raise a Glass at these DeLand Bars and Lounges

If you’re up for some interesting bartender chatter, grab a stool at a local tavern. Within The DeLand Hotel, Hemingway’s Bar & Lounge has a way with craft cocktails.

If you’re more in the mood for a pit stop to catch the game on a large screen, pop over to Half Wall, where you’ll see a wall full of beer taps, including local brews from DeLand and the surrounding area.

Other options include City Limits Taproom and The Blind Pig.

Cocktails from The Table in downtown DeLand – image by Dani Meyering

LEARN

Stetson University

421 N. Woodland Blvd, DeLand, FL32723

You don’t need to be an enrolled student to learn here. Check out Stetson’s events page to find guest speakers, screenings, and other community happenings. After all, smart is the new sexy, right?

Hontoon Island State Park

2309 River Ridge Road, DeLand FL 32720

This island is accessible only by private boat or park ferry so getting there is half the fun! Canoe and enjoy a picnic lunch, then pop into the Hontoon Island Museum to learn about the area’s first inhabitants to gain an understanding of their past and natural habitats.

Pulptown's Guide to Downtown DeLand — Hontoon Island State Park | Image credit: Florida State Parks

Check out our complete guide to Visiting Hontoon Island State Park.