The 8 Hipster Districts of Orlando to Explore Like a Local

Venture off the beaten path with this guide to popular districts in Orlando for soaking up the arts, dining and shopping experiences that locals love.

Orlando is known around the world as a theme park playground for children and adults alike. Yet visitors often miss out on the relatively undiscovered sections of Orlando, cherished by locals as up-and-coming cultural havens. In our humble opinion, these neighborhoods—your friends may not have heard of them yet—are a destination vacation in and of themselves.

Explore our suggestions tailored with a fine, hipster lense on the best neighborhoods to adventure through.

Thornton Park
Graffiti Junction in Thornton Park is a great place to play trivia or watch the game while chowing down on some of Orlando's best burgers. (@Thornton Park District)

Thornton Park

Just east of Lake Eola Park and Orlando’s bustling downtown financial district, this quaint shopping, dining and arts village with brick-lined streets and European atmosphere is one of the city’s most stylish districts.

Here you’ll find locals dining alfresco at upscale restaurants like Soco and Dexter’s, enjoying craft-beer and wine while perusing local art at The Falcon Bar & Gallery or getting stylish at one of the many hair salons and fashion boutiques. You won’t want to miss Thornton Park’s "Wine Walk + Art Stroll" happening every second Thursday of the month.

Audubon Park
Monthly cyclist meet-ups gather outside Audubon Park's famous Bikes, Beans & Bordeaux cafe. (©Audubon Park Garden District)

Audubon Park

Tucked around a retro residential neighborhood known for its gardens and wild peacocks, Audubon Park is home to award-winning, farm-to-table restaurants, boutiques, live-music venues and a thriving nightlife scene. Just a short walk from beautiful Harry P. Leu Gardens, a 50-acre botanical oasis, and anchored on its east side by expansive Blue Jacket Park, Audubon Park is registered by the National Trust for Historic Preservation and is an accredited Main Street program as well as an Orlando EcoDistrict.

The area also hosts some of Orlando’s most original events including street parties, costume balls, regular happy-hour socials, book readings, wine tastings, foodie events, kid-friendly activities, guest lectures, cult TV trivia nights, bicycle rides and adventure races. You won’t want to miss the community market that takes place every Monday evening from 6-10 pm outside Stardust Coffee & Video. This weekly gathering of growers, ranchers, fishermen, chefs, artists, hand-crafters, musicians and neighbors is a hometown hangout where visitors can shop for handmade goods and fresh, local fare.

Among the many reasons to visit, specific highlights include Blue Bird Bake Shop, known for some of the best cupcakes in the area; East End Market, which is full of unique local vendors and home to Central Florida’s foodie movement; Park Ave CDs with its full calendar of in-store performances by touring bands and Redlight Redlight Beer Parlour, renown for its huge selection of crafts-brews.

Milk District
The Milk District is a favorite among hip locals and celebrities alike, especially on "Tasty Tuesdays" when food trucks take over the dining scene. (©The Daily City)

The Milk District

The area aptly named for the T.G. Lee Milk national headquarters smack-dab in its center, the Milk District is a dining, shopping and nightlife district that dates back to the 1950s.

Hungry locals—and even visiting celebrities including Jimmy Fallon—frequent Beefy King, an Orlando institution since 1968 and one of only two of the original roast beef fast-food sandwich joints in the United States. For fashionistas, Etoile Boutique features eclectic, handmade and vintage clothing and accessories that never go out of style. Here you’ll find local brands, wearable art pieces, vintage items including hats, ties and suspenders and products made from recycled goods. The nearby Plaza Live Theatre, opened in 1963 as Orlando’s first twin-screen movie venue, is now one of Orlando’s premier live venues, showcasing both local and touring artists.

A happening nightlife scene surrounds the hip bar-strip that’s home to funky watering holes like Milk Bar, Spacebar and Sandwich Bar, as well as the weekly food truck bazaar "Tasty Tuesday." For traditional bar entertainment, head to Sportstown Billiards. This cavernous pool hall has the best craft-beer selection and prices in town and also features pingpong, air hockey, foosball, skee-ball and various board and console games.

Plant Street Market
From a local butcher shop to European bakery, artisan chocolate to in-house roasted coffee, gourmet pub grub to craft-beer brewed on-site, you'll find it all at Plant Street Market in historic downtown Winter Garden. (©Plant Street Market)

Historic Downtown Winter Garden

Cobblestone streets lined with ancient oaks make the sun-dappled historic downtown of Winter Garden a picturesque destination for the whole family. Listed on the National Registry of Historic Places, the former citrus town hosts one of the top regional Farmers Markets in Central Florida and is home to the thriving new Plant Street Market, which houses a variety of local vendors and eateries as well as celebrated Crooked Can Brewery.

A great location to spend a lazy weekend day or evening, here you’ll find relaxing swings around the fountain and clock-tower gazebo, a fun splash pad for the kids to cool off and the West Orange Trail, perfect for cyclists and joggers, that runs through the center of town.

Concerts and productions at the historic Garden Theatre, exhibits at the SoBo Art Gallery and sunsets over nearby Lake Apopka are not to be missed.

Jack Kerouac House
The Jack Kerouac House near College Park hosts aspiring writers and literary events. (©Wikimedia Commons)

College Park

The quiet yet urban bungalow neighborhood of College Park derives its name from its many streets named for colleges like Princeton, Harvard and Yale.

Ride the bike lane-laden main drag to peruse local retailers and award-winning restaurants as well as the 1950s-era Publix. Enjoy a healthy lunch at Infusion Tea before indulging in hand-made ice cream, shakes, malts and sundaes from The Soda Fountain.

Nestled just outside downtown is the historic home of Jack Kerouac, whose house still stands as a literary museum and host to writers-in-residence.

White Wolf Cafe in Orlando, Florida
White Wolf Cafe is the perfect place for brunch or dinner in Ivanhoe Village. (©White Wolf Cafe)

Ivanhoe Village

Formerly Orlando’s historic “Antique Row,” this unassuming stretch of old Orlando lakefront is a walkable and bicycle-friendly district home to eclectic dining, funky shops and swanky nightlife.

If brunch is your happy-place, visit White Wolf Café and Bar or Santiago’s Bodega for some of the best bloody marys, mimosas and small plates in town.

For a sophisticated evening, check out the Imperial Wine Bar at Washburn Imports; a dark-wood, global-imports store by day and intimate craft-beer and wine bar by night. On the opposite side of the nightlife spectrum is the Hammered Lamb, a casual haunt for bar bites and hefty train shots out on the garden-district-like patio.

In terms of entertainment, here you’ll find Orlando’s cultural corridor where you can take your pick from high-brow burlesque at The Venue, classic and contemporary art at Mennello Museum of American Art and Orlando Museum of Art, live theater at the Orlando Shakespeare and Repertory theaters or mind-expanding, hands-on exhibits at the Orlando Science Center.

Mills 50 District
Mills & Lake Highland.

Mills 50

Described as Orlando’s intersection of culture and creativity, this hipster hub fosters a mix of artists, restaurants, businesses, specialty shops, markets and bars. You’ll know you’re in the right place when you see larger-than-life surrealist graffiti and murals covering walls, dumpsters and electric boxes.

Here you’ll find unofficial Orlando landmarks like Colonial Photo & Hobby Shop, Track Shack, Wally’s Liquors and Will’s Pub.

The district is also home to Orlando’s Asian community where restaurants like Hawker’s, Mamak, Pho 88 and Little Saigon create an affordable and eclectic concentration of alternative dining options. Look to the Black Bean Deli for authentic Cuban cuisine and Anthony’s Pizza for a taste of New York. Tako Cheena is a must-visit for foodies who love funky fusions of local ingredients served late into the night.

But if you really want the hometown vibe, head to the somewhat hidden Dandelion Communitea Café, a vegetarian teahouse set in a historically refurbished and colorful, bungalow-style home. Check out the “Dandy” for nightly events and performances as well as monthly full- and new-moon parties and drum circles.

Church Street District
Church Street in downtown Orlando has a rich history as a popular entertainment district and is home to Orlando's sports scene. (©Church Street District)

Downtown Orlando/Church Street District

With history dating back to the 1800s, Historic Church Street juxtaposes the past with the present. The downtown home of Orlando’s top entertainment venues, the Church Street District features an eclectic mix of fine dining, professional sports, live entertainment and booming nightlife.

Ride the SunRail from any of the Central Florida stops to Church Street Station where you can enjoy upscale restaurants like Artisan’s Table, Ceviche, Rusty Spoon and Kres Chop House.

After dinner you can take in some culture by attending a performance at Mad Cow Theatre, one of Orlando’s most respected professional theatre companies, or the new, state-of-the-art Dr. Phillips Center for the Performing Arts.

Sports fans can cheer on the Orlando Magic at the nearby Amway Center or Orlando City Soccer at the Citrus Bowl just down the road. Music lovers can see their favorite bands perform at The Social and the Beacham Theater, some of Orlando’s premier live venues.

Grab drinks at one of the many area bars including One 80 Grey Goose Lounge, a sophisticated vertical retreat featuring unparalleled views from its perch nestled below the spire of the Amway Center, or Latitudes, downtown Orlando’s tiki-inspired rooftop bar, where the sky is the ceiling and the skyscrapers are the walls.

Map: The 8 Coolest Orlando Neighborhoods