Discover Historic DeLand on a Date Day Trip

ByNancy Devault Updated Things to do
Date Daytrip to Historic DeLand

Craving a charming escape with your special someone? Look no further than DeLand, Florida! This vibrant town, nestled just a short drive or SunRail ride 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 September 2025

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.

READ MORE: 10 Things to Do on a Sunday in Orlando

DeLand House Museum

137 W Michigan Ave, DeLand, FL 32720

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.

Athens Theatre

124 North Florida Avenue, DeLand, FL 32720

Designed in 1921, the Athens Theatre is one of the remaining classic American theatres. It opened in 1922 and originally featured vaudeville acts and silent movies. The theatre has evolved significantly over the years, once serving as a home to a dinner theater, video game room, and prom parties!

Now, the theatre is home to a range of entertainment, including musicals, comedy shows, live concerts, movies, dance performances, and more. Catch your favorite show at the theatre for a fun matinee or evening night out.

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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 remain in place until 2025.

Pat & Toni's Sweet Things

124 N Woodland Blvd, DeLand, FL 32720

Treat yourself to some handmade sweets! Named Best of Florida three years in a row, Pat & Toni's Sweet Things is the perfect place to pick up fresh chocolate or indulge in a sweet and savory snack.

There's something to satisfy any sweet tooth, with seasonal items such as caramel apples, blueberry pie Oreo balls, Dubai-style pistachio liquor truffles, as well as year-round hand-dipped chocolates and fudge.

Check out More Shops

Historic Downtown DeLand is home to multiple boutiques to explore.

DINE

Persimmon Hollow Brewing Company

111 W Georgia Ave, DeLand, FL 32720

You may recognize the name of this brewery, as it had 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.

A thick beer glass with the logo of Persimmon Hollow Deland sits on a table
Persimmon Hollow Deland – Dani Meyering

The Twisted Chopstick

111 W Georgia Ave, DeLand, FL 32720

If you love Japanese cuisine, then this is the place for you. Owner and Executive Chef, Jeoffrey Curtis, learned the basics and art of Japanese cooking from his mother and has been cooking for over a decade, opening The Twisted Chopstick in 2017.

The restaurant offers a variety of dishes, including sushi rolls, sashimi, poke bowls, ramen, bento boxes, and sushi burritos, with indoor and patio seating. Plus, you can enjoy lunch specials during the week from 11:30am – 3pm, Tuesday-Friday, and Sushi Saturdays (3 Rolls for $20).

Check out More Local Restaurants

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

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 Abbey Bar and The Elusive Grape. 

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

Check out more lounges

Sit back, relax, and enjoy good conversation over food and drinks.

LEARN

Stetson University

421 N. Woodland Blvd, DeLand, FL 32723

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?

DeLand House Museum

137 W. Michigan Avenue, DeLand, FL 32720

Learn about the history of West Volusia, discover WWI and WWII artifacts, and explore galleries, including the West Volusia Black Heritage Gallery, and more. This historic Victorian-style house was built in 1886 by Henry Addison DeLand, previously known as the Frame Vernacular house. It later underwent renovations and opened as a museum in 1990.

House tours are available Tuesday through Saturday at 12:30pm and 2:30pm.

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 and 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.

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Feature image credit: blog.eragrizzard.com

Nancy DeVault is a fitness enthusiast, news junkie, shoe lover, adult beverage fan and travel addict. She works as a Florida-based freelance writer and editor. Nancy is always down for date night, girls night out and family fun adventures.