Crooked Can Brewery in Winter Garden Near Orlando

Expect the Unexpected in Orlando Neighborhoods

Think you know Orlando? If you’ve only experienced our tourism districts, think again! Beyond the theme parks and attractions, Orlando’s neighborhoods and nearby cities offer endless adventures with dining, nightlife, arts & culture, outdoor recreation, shopping, and other surprises that locals love — and that you deserve to experience during your next visit. And now, you can get a sneak peek before you even arrive via Tripadvisor's Visit Orlando Experience on Alexa. Just say, “Alexa, launch Visit Orlando!” 

What’s more, the Main Street America-accredited Orlando Main Streets program makes it a snap to track down eclectic neighborhoods that are worth your attention, with a focus on distinct areas that stretch from Orlando International Airport (MCO) to downtown Orlando and beyond. While intriguing neighboring cities aren’t included in Orlando Main Streets, they’re also easy to find, with most being located no more than 30 minutes from downtown Orlando.

So, secure a rental car, taxi or ride-share service, or hop on a tour bus or the SunRail commuter train service — it’s time to explore the unexpected side of Orlando! 

Please note: Depending on the timing of your visit, some experiences may be temporarily modified. Learn more about healthy travel in Orlando, and check with your favorite attractions, restaurants and other businesses for their current status.

Orlando Main Street Districts

The following Orlando Main Street districts include downtown Orlando and its adjacent neighborhoods. If you’re only visiting the destination for a limited time and want a taste of local living, these are the areas that best deserve your attention.

Aerial photo of downtown Orlando and Lake Eola
Lake Eola Park in Downtown Orlando

City District and Parramore

Our central Main Street District encompasses the dynamic heart of downtown Orlando and provides immediate access to many other neighborhoods you’ll want to visit. This is where “authentic Orlando” begins!

Learn more: Downtown Orlando

First up, City District and Parramore host a majority of the city’s professional and collegiate sporting events. These include the NBA’s Orlando Magic and ECHL’s Orlando Solar Bears at the Amway Center, the MLS’ Orlando City Soccer Club and NWSL’s Orlando Pride at Exploria Stadium, and NCAA bowl games and other matchups at Camping World Stadium.

Learn more: Orlando Sports

If you seek culture, make a date with downtown’s state-of-the-art Dr. Phillips Center for the Performing Arts, which hosts Broadway productions, the Orlando Ballet, concerts, comedians and more. You can also enjoy live music at the Amway Center, Camping World Stadium, the Beacham Theatre and several intimate venues, as well as improv at SAK Comedy Lab. Alternately, the Orange County Regional History Center and Heritage Square Park spotlights 12,000 years of Central Florida history, while the historic Wells’Built Museum explores African-American culture and our region’s contributions to the civil rights movement. You can even view varied, rotating exhibitions from local and international artists at CityArts, a funky collective of independent art galleries.

Learn more: Downtown Orlando Virtual Tour

City District boasts an enticing variety of dining and nightlife, too. Acclaimed downtown restaurants include Artisan’s TableThe Boheme at Grand Bohemian Hotel OrlandoDoveCote Restaurant, Reyes Mezcaleria, and 310 Lakeside.

Try the motor-centric Ace Cafe Orlando for a mix of pub fare and nightlife, including live music on select nights, or grab a brew at Motorworks Brewing. You can also chase the night at Wall St. Plaza, which features seven different themed bars, or the Sky Lounge at Amway Center, among other options. Or, take in an evening of risqué entertainment at HÄOS on Church, close to Exploria Stadium.

Learn more: Orlando Breweries

Plenty of great businesses await in the Parramore area, too. The city’s only commercial National Register Historic District is home to restaurants such as Foodies Cafe and Nikki’s Place Southern Cuisine, plus retailers that include Neu Blooms, Popcorn Junkie, Chloe Lane Embroidery and Palmer Feed Store, among others.

Last but not least, be sure to visit Lake Eola Park, the crown jewel of downtown Orlando. Take a ride on one of the park’s rentable, swan-shaped paddleboats for a trip around the namesake lake, and you’ll see why we’re called The City Beautiful!

Learn more: Orlando Public Parks

Exterior of Russell's on Lake Ivanhoe in Orlando during the day
Russell’s on Lake Ivanhoe in Downtown Orlando

Ivanhoe Village Main Street

Adjacent to downtown Orlando, Ivanhoe Village Main Street has something for just about everyone, including historic homes, acclaimed dining, cultural venues, specialty shopping and funky street art. Until its revival as a nightlife hub, the district’s namesake thoroughfare, Ivanhoe Boulevard, was colloquially known as Antique Row. While you can still get in some quality antiquing when you visit, the district has added many forward-looking retailers, too.

Learn more: Ivanhoe Village

But make no mistake: dining and indie flair are the main draws here. For upscale-casual dining with an unbeatable view, reserve a table at Russell’s on Lake Ivanhoe, overlooking its beautiful namesake. Other delicious Ivanhoe Park eateries include Santiago’s Bodega, The Greek Corner, Ta-Ke Sushi Bar and White Wolf Cafe.

The homegrown beers at Ivanhoe Park Brewing Company serve as an excellent complement to the district’s dining options. Other bars and lounges include The Lucky Lure, The Imperial at Washburn Imports, Hideaway Bar, Nora’s Sugar Shack and The Matador, as well as LGBTQ+ venues such as The Hammered Lamb and Savoy Orlando.

Learn more: LGBTQ+ in Orlando

Even nature-lovers will enjoy Ivanhoe Village, which connects to the Orlando Urban Trail. The 3-mile path runs from Lake Highland in Orlando to Mead Botanical Garden in Winter Park, passing six gorgeous lakes along the way.

Aerial shot of the exterior of the Orlando Museum of Art
Orlando Museum of Art at Loch Haven Cultural Park in Orlando

Loch Haven Cultural Park

Although it’s not a neighborhood, this unique, 45-acre public park is part of Ivanhoe Village Main Street district, adjacent to Audubon Park Garden District and Mills 50, and minutes from downtown and other Orlando districts. More importantly, it’s home to museums and galleries that are must-visits for patrons of the arts.

Learn more: Orlando Museums & Galleries

Venues include Orlando Museum of ArtThe Mennello Museum of American Art, Orlando Shakespeare Theater (aka Orlando Shakes), Orlando Repertory Theatre (aka Orlando Rep), Orlando Fire Museum and the headquarters of Orlando Ballet, which performs at downtown’s Dr. Phillips Center for the Performing Arts.

In May, Loch Haven Park hosts the Orlando International Fringe Theatre Festival, aka Orlando Fringe, which is the longest-running event of its type in the U.S. The park also has Orlando Science Center, one of our best STEM attractions.

Learn more: Orlando STEM Attractions

A large white and green sign with the Se7en Bites logo stands above a lime green arch, with blue skies behind it, in Orlando, Florida.
Se7en Bites in Orlando’s Milk District

The Milk District

About 10 minutes east of downtown Orlando, The Milk District is named after its centrally located T.G. Lee dairy plant, which features an eye-catching, rooftop cow statue. This area serves as a progressive lifestyle, music and cultural hub, and it also has plenty for gourmets.

Dining options include one of Orlando’s oldest: Beefy King, which has been serving an award-winning selection of hot sandwiches and crispy tater tots for more than 50 years. The district also lays claim to Stasio’s Italian Deli & Market, MX Taco, and Se7en Bites. Food Network fans might recognize the latter’s award-winning Chef Trina Gregory-Propst, who’s been featured on Guy Fieri’s Diners, Drive-Ins and Dives and Guy’s Grocery Games.

Another major draw for foodies is Tasty Takeover, a weekly food truck event that takes place on Tuesday nights. In fact, the program has been so successful that it inspired the launch of A La Cart Orlando, where long-term and mobile vendors serve some of Orlando’s best street-food fare and locally produced beers.

The Milk District has numerous places to catch live music, too, starting with The Plaza Live, which hosts the Orlando Philharmonic and a wide range of shows. You can also see bands at Southern Craft, The Nook on Robinson, and Whiskey Lou’s Lounge. Other places to get a drink in The Milk District include Sideward Brewing Co., Sportstown Billiards and LGBTQ+ nightclub Southern Nights.

For shopping in The Milk District, stop by the Milk District Spot to see local homegrown vendor pop-ups. While you’re at it, visit the other retail and restaurant locations along Robinson Street and Bumby Avenue, including Etoile Boutique and Pom Pom’s Teahouse & Sandwicheria, which is open late night to serve up popular sandwiches — especially the Mama Ling Ling’s Thanksgiving Sandwich! Nearby, Colonial Plaza is a walkable, open-air center with a mix of national and local retailers, plus some tasty restaurants. Several smaller shops can also be found along Mills Avenue and Colonial Drive.

A colorful mural featuring a DJ, disco ball, and a dancing woman on the side of a building in the Mills 50 area of Orlando, Florida.
Large-Scale Murals Are a Hallmark of Orlando’s Mills 50 District

Mills 50

Featuring colorful, large-scale street murals created by professional artists, and heavily influenced by Asian and Pacific-Islander culture, Mills 50 is named after its main, intersecting streets: Mills Avenue and State Road 50 (aka Colonial Drive). One of Orlando’s oldest neighborhoods, the district has transformed into a nightlife hotspot in recent years, up to and including making its own alcohol at Quantum Leap Winery and Ten10 Brewing Co.

Learn more: Mills 50

Mills 50 doesn’t lack for bars and lounges, either. Will’s Pub and its sister venue, Lil Indies, are some of the best places to see live music, particularly if your tastes run to the eclectic side. Even without entertainment, Will’s is a memorable place to get a drink. Grumpy’s Underground and Wally’s Mills Avenue Liquors offer unique ambience of their own.

You certainly won’t go hungry while visiting Mills 50, not with eateries like The Strand Food & Drink and Bites & Bubbles. Eastern cuisine is king, though, including options like Chuan Lu Garden, Nha Trang Subs, Little Saigon, Hawkers Asian Street Fare, Mamak Asian Street Food, Poke Hana, Pop Thai, Shin Jung Korean Restaurant, and Yamasan Sushi & Grill. Just east of Mills 50 proper, Kabooki Sushi serves the creations of James Beard Award-nominated Chef Henry Moso.

Learn more: Asian-American and Pacific Islander History & Culture

If you prefer Hispanic and Latin flavors, stop by Black Bean Deli or Black Rooster Taqueria. And for sublime fusions, try Pig Floyd’s Urban Barbakoa or Tako Cheena.

Learn more: Hispanic and Latino History & Culture

This neighborhood’s unique character extends to its retailers. One of the oldest is Colonial Photo & Hobby, where you can get the latest camera gear or feed your favorite pastimes. Other notable stores include Dong A Imports, Lacastro Store and Out of the Closet Thrift Store. And for pure pampering, it’s tough to beat Mills 50’s collection of full-service spas and salons.

A street view of the Thornton Park neighborhood featuring a fountain and restaurant in the background.
Downtown Orlando’s Thornton Park District

Thornton Park District

On the east side of Lake Eola Park in downtown Orlando, Thornton Park District is a stylish dining and nightlife area known for brick-lined, canopied streets with a distinctly European feel.

A local favorite for dining, Maxine’s on Shine is nestled between Thornton Park District and Mills 50, and it’s a must-visit when you’re in this area. Thornton Park is home to several other delicious eateries, including local favorites such as Soco Restaurant, The Stubborn Mule, RusTeak Thornton Park, Jinya Ramen Bar, Anthony’s Pizzeria & Restaurant, The 808, Island Time, Cavos Bar & Kitchen, and Mason Jar Provisions.

This district has many unique ways to light up the night, too — literally in the case of Stardust Lounge, an underground club that features retro-chic Vegas stylings and shares a building with Aku Aku Tiki Bar, which is upstairs. Thornton Park’s entertainment options also include The Abbey, a unique venue that hosts themed music nights and live theater.

Visitors outside of the OnePulse Foundation Memorial at night
Pulse Interim Memorial in Orlando

SoDo District

As its name implies, this increasingly lively district is south of downtown Orlando. At the very south end approaching the city of Edgewood, you’ll find one of Orlando’s most acclaimed, longest running restaurants, Le Coq au Vin, which is a must-visit for connoisseurs of French cuisine. Nearby, Delaney’s Tavern specializes in friendly, New American fare and spirits.

More delicious fare can be had at Brick & Fire Pizza, Mediterranean Blue, Numero Uno Cuban Cuisine, Clean Eatz, SoDo Sushi Bar & Grill, Johnny’s Fillin’ Station, The Aardvark, Shaka Donuts and Shaka Ice, and Sugar Divas Cakery. For nightlife, try Orlando Brewing (Orlando’s oldest microbrewery), Rockpit Brewing and Swirlery Wine Bar. You can get your shop on in SoDo, too, with options like Freshfields Farm, Fleet Feet and Foreign Accents.

SoDo is also home to the Pulse Interim Memorial. Located on the site of the former Pulse nightclub, this temporary memorial is dedicated to a hopeful future where all people will be free to live their own truths. Free to visit, it’s open daily from 7:30 a.m. to 9 p.m., with extended hours during Pulse Memorial Week and select holidays.

A statue of a frog trimming a shrub at Harry P. Leu Gardens.
Harry P. Leu Botanical Gardens in Orlando’s Audubon Park District

Audubon Park Garden District

Audubon Park Garden District is a Great American Main Street Award-winning community, located 15 minutes from downtown Orlando. It is the hub of Orlando’s organic movement, thanks to an organic community garden and urban “farmlettes” created in part by Fleet Farming, which teaches homeowners how to grow their own food.

The area’s west side also has Harry P. Leu Botanical Gardens, offering 50 acres of beautifully cultivated flowers and plants. In 2019, the National Wildlife Federation designated the Audubon Park Garden District as the region’s only Community Wildlife Habitat, making it the first in Central Florida and the 18th in the State of Florida to receive this honor.

Learn more: Audubon Park

The charming district is anchored by East End Market, where you can purchase farm-to-table cuisine and artisanal merchandise. One of the best reasons to visit this venue is Gideon’s Bakehouse, which specializes in small-batch, handcrafted cookies and cakes. In fact, Gideon’s is so popular that they had to open a second location at Disney Springs®. East End Market also houses La Femme du Fromage, Winter Park Biscuit Co., Old Hearth Bread Company, Domu, La Boutique, and Dochi Donuts. The district’s main strip, Corrine Drive, has more can’t-miss sweetshops, including P Is for Pie Bakery, The Salty Donut and Kelly’s Homemade Ice Cream.

For main courses, try the sandwiches at Bikes, Beans & Bordeaux Cafe. Other options include Kadence, Sushi Lola, Bem Bom, 1803 Pizza Kitchen, and Junior’s Diner & Mexican Grill. And when you’re ready for a good brew or spirits, head to Redlight Redlight Beer Parlour or Stardust Video and Coffee, the latter of which boasts an impressive Scotch collection. Finish off your evening and show off your vocal skills at Big Daddy’s with nightly karaoke beginning at 9 p.m.

Guests dining in the outdoor patio at The Tap Room at Dubsdread in College Park
The Tap Room at Dubsdread in Orlando’s College Park Neighborhood

College Park Main Street

Orlando is one of several U.S. cities with a College Park area. But whereas most are designated as such because they’re close to a college, ours derives from the fact that many of its streets are named after famous colleges. While you’re there, see if you can find your own alma matter!

Learn more: College Park Main Street

The college-named streets are not the only quirky aspect about this traditional, walkable, neighborhood commercial district, which pairs a hometown, close-knit community feel with superb dining, shopping and cultural opportunities, just 10 minutes from downtown Orlando. Famed author Jack Kerouac liked the area so much that he started writing The Dharma Bums while living in College Park from 1957 to 1958, which is the same period during which On the Road was published. Today, the historic home gives burgeoning writers a place to live and hone their craft as part of The Kerouac Project.

College Park has much for shoppers, too, including one-of-a-kind finds at Driftwood Market, Bijou’s Boutique, Ritzy Rags and Top Drawer Consignments. You’ll also find everything you need for bicycling at Orange Cycle, hip music and clothing at Foundation, handcrafted bath and body products at Naked Bar Soap Co., and even cosplay gear at Embellish FX.

Learn more: Neighborhood Shopping

This district’s culinary options range from counter-service to fine dining. Highlights include The Taproom at Dubsdread, The Soda Fountain, Southern Home Bakery, Armando’s, Jade Sushi & New Asian, Tin & Taco, College Park Cafe, Christo’s Cafe, and Trevi Pasta.

A bartender pours a draft beer from the tap at Roque Pub.
Roque Pub

Curry Ford West

Curry Ford West is one of the city’s Market Streets, a sub-designation of the Orlando Main Streets program. Curry Ford West is set apart from other districts with its distinct, mid-century modern-inspired design and architecture, and commitment to being a truly family-friendly neighborhood focused on embracing the deep community roots. In fact, many families have lived in the neighborhood for multiple generations! The district runs along Curry Ford Road and is about 15 minutes from the city’s core and a short walk or bike ride from beautiful Lake Underhill Park.

You’ll find a vast collection of beer in Curry Ford West — both locally brewed and from around the world — at venues like Roque Pub, The Commission Beer Chamber, Claddagh Cottage Irish Pub and Hourglass Brewing.

Meanwhile, this district’s restaurants bring international flare to the table, encompassing Cuban, Greek, Irish, Italian, Lebanese and Mexican cuisine — not to mention some of the best pizza in Orlando courtesy of Pizza Bruno. Some local favorites include La Fiesta Mexican Grill, JJ’s Fresh From Scratch, Daybreak Diner, Uncommon Catering & Eatery, Cilantro’s Taqueria, Kathi Rolls, Theo’s Kitchen, Papa Llama, and more. While you’re there, make sure to stop and snag a cookie from Charlie’s Bakery, one of Orlando’s oldest bakeries, having served the community now for more than 50 years.

An airplane preparing for takeoff at Orlando International Airport
Orlando International Airport

Gateway District

Designated as an official Orlando Market Street, Gateway District stretches northward on Semoran Boulevard from Orlando International Airport to State Road 408, making it the primary route for visitors who have just touched down in Orlando. It’s known as the world’s gateway to Orlando and Orlando’s gateway to the world!

Gateway District is an international area and a melting pot of cultures and cuisines, including deep roots in Hispanic and Latino culture. The area has numerous restaurants, nightspots and retailers, including notables such as Rock & Brews, El Cafetal Bakery & Restaurant, Bonchon Orlando, High Tide Harry’s, Oh Que Bueno, El Cilantrillo, Thai Island, and Napoli Italian Pizzeria.

Whether you’re looking to shop small or visit large-scale retailers, the Gateway District is the place to be: dd’s Discounts, Shoe Land, Kiara Beauty Supply, Ulta, Beall’s Outlet, Five Below, Michaels, Walmart, and Petco to name a few! Visit the new mural in the Gateway District at Sedano’s Supermarket for a photo-op, too.

The perfect date night could be a trip to the Gateway District’s own Marlow’s Tavern for a delicious dinner, followed by a feature film at Epic Theatres in the Lee Vista Promenade. In the Gateway District, there’s something for everyone.

More Orlando Neighborhoods & Nearby Cities

The following cities, towns and neighborhoods are destinations in their own right. Better still, all are about 30 minutes or less from downtown Orlando.

Park Avenue in Winter Park
Park Avenue in Winter Park Near Orlando

Winter Park

Luxury-minded visitors won’t want to miss the charms and wonders of Winter Park, located 20 minutes northeast of downtown Orlando. Along its tree-lined, cobblestoned streets, you’ll encounter some of Central Florida’s finest dining, acclaimed museums and galleries, exquisite shopping opportunities, and natural splendor. We’d call it a hidden gem, but the charming city’s reputation precedes itself!

Learn more: Winter Park

Winter Park’s epicenter is Park Avenue, a gorgeous, walkable thoroughfare that runs along Central Park with restaurants, museums and exceptional shopping. It terminates at Rollins College, which boasts the Rollins Museum of Art. Offering free admission, the facility houses more than 5,600 pieces of art ranging from the ancient to modern periods.

A portion of the museum’s offerings is displayed as the Alfond Collection of Contemporary Art at The Alfond Inn, a stately hotel that’s also operated by Rollins and is home to a farm-to-table eatery, Hamilton’s Kitchen. Other museums in Winter Park include The Charles Hosmer Morse Museum of American Art, featuring a massive selection of work by Louis Comfort Tiffany, and the Albin Polasek Museum & Sculpture Gardens, dedicated to its namesake artist.

Learn more: Winter Park Virtual Tour

These offerings are complemented by the annual, nationally recognized Winter Park Sidewalk Art Festival in March, as well as October’s Winter Park Autumn Art Festival, which exclusively features Florida artists. If you prefer live entertainment, get tickets to The Winter Park Playhouse, or enjoy live music and a tour of historic Casa Feliz on Sunday afternoons.

When you’re ready to eat, you can’t go wrong with The Ravenous Pig, a seasonal gastropub headed by James Beard-nominated Chefs James and Julie Petrakis, who also run The Polite Pig at Disney Springs. Another James Beard nominee, Brandon McGlamery, is the driving force behind Park Avenue’s Prato, as well as Luke’s Kitchen in nearby Maitland. Other can’t-miss Winter Park eateries in the immediate Park Avenue area include blu on the avenue, Chez Vincent, 310 Park South and Umi Sushi. More great restaurants are just a short drive away, including The Glass Knife, Bulla Gastrobar, Christner’s Prime Steak & Lobster, Reel Fish Coastal Kitchen, and Rocco’s Italian Grille & Bar.

Learn more: Orlando’s Top Chefs

Meanwhile, Park Avenue’s collection of boutiques challenge you to shop till you drop with fashion, jewelry, books, gifts and much more, including options that range from high-end local boutiques like The Ancient Olive Gourmet to nationally recognized retailers. Just a short drive from Winter Park’s core, Winter Park Village has even more shopping and dining.

Finally, don’t skip on Winter Park’s many opportunities for outdoor activities and relaxation, starting with the Winter Park Scenic Boat Tour. It will give you a taste of Winter Park’s chain of lakes, which encompass 2,781 acres of pristine waterways over 12 major bodies of water. The city also has 11 amenity-laden public parks as well as the Winter Park Golf Course, which has nine holes and is on the U.S. National Registry of Historic Places.

A group of people gathered inside Boxi Park in Lake Nona at night
Boxi Park in Orlando’s Lake Nona District

Lake Nona

Less than 10 minutes from Orlando International Airport and 20 minutes from downtown Orlando — but still inside Orlando city limits —  Lake Nona is a globally recognized, 17-square-mile community that’s home to superb dining, one-of-kind entertainment experiences, world-class sports venues, hundreds of annual events, one of Central Florida’s most robust public art programs, and some of the region’s most gorgeous scenery. And in fall 2021, it’s adding all-new, state-of-the-art, boutique accommodations courtesy of the Lake Nona Wave Hotel.

Learn more: Lake Nona

Many of the top reasons to visit this area can be found at Lake Nona Town Center. Here, you’ll find chef-driven restaurants like Chroma Modern Bar + Kitchen and Canvas Restaurant & Market, exceptional Turkish fare at Bosphorous, and wood-fired pizza and house-brewed beer at Park Pizza & Brewing Company.  More great food, plus beach volleyball, nightly live entertainment, a kids' playground, a dog park and more, can be enjoyed at Boxi Park, a deconstructed food hall built from repurposed shipping containers.

Learn more: Lake Nona Virtual Tour

Just a short drive away, you can cool off at Nona Adventure Park. Test your skills on a floating aqua park, a cable park for wakeboarding and waterskiing, a climbing tower, and a ropes course, plus a pro shop and bistro. Play like the pros on the tennis, padel or pickle ball courts of the U.S. Tennis Association National Campus, the largest tennis campus in the world. And when you’re ready to practice your swing, head over to Drive Shack Orlando, which turns golf into fun games like Monster Hunt and the blackjack-influenced ShackJack.

A woman views a large mural of Zora Neale Hurston in Eatonville
Zora Neale Hurston Mural in Historic Eatonville Near Orlando

Historic Eatonville

Historic Eatonville, located about 15 minutes north of downtown Orlando, has much for art and history aficionados. Part of the Florida Main Street program, it’s one of the oldest African-American municipalities in the United States, having been incorporated in 1887. No less important is that the town was the childhood home to celebrated author Zora Neale Hurston (Their Eyes Were Watching God), whose legacy continues to be felt to this day.

Learn more: African-American History & Culture in Orlando

Hurston is honored at the Zora Neale Hurston National Museum, aka the Hurston, which serves as a memorial to its namesake and provides gallery space to artists of African descent. While donations are encouraged, admission is always free.

Eatonville also pays homage to the author with the annual Zora Neale Hurston Festival of the Arts and Humanities, aka ZORA!® Festival. Held at locations in Eatonville and around the Orlando area, the week-long celebration focuses on the arts and education, including several events that are free to attend. The festival traditionally takes place in late January and early February.

Some of the Orlando area’s best Black-owned restaurants can be enjoyed in Eatonville, too. Top options include Brick & Spoon, Mad Crab Seafood & Wings, and Soul Food Fantasy.

A row of shops in downtown Winter Garden
Plant Street in Winter Garden

Winter Garden

Not to be confused with Winter Park, the city of Winter Garden is one of Central Florida’s most beloved communities. You could easily spend a day or more exploring its dining, nightlife, entertainment and outdoor adventures, all just 30 minutes west of downtown Orlando and 20 minutes north of Walt Disney World® Resort.

Learn more: Winter Garden

Running through the middle of the city’s bustling downtown district, Plant Street boasts historic architecture and superb dining and entertainment. It’s anchored by Plant Street Market, home to Crooked Can Brewing Company and numerous eateries and lounges. Plant Street Market itself is a gourmet’s dream, with a range of cuisines that pair perfectly with the brewery’s house-made beer selection. RusTeak Restaurant & Wine Bar and Urban Flats are other top choice for foodies in Winter Garden.

Plant Street also has the Garden Theatre, which dates to 1935 and hosts a robust schedule of live theater and concerts, plus classic films. Also in this area, the Winter Garden Heritage Foundation operates the Winter Garden Heritage Museum and the Central Florida Railroad Museum, while American Ghost Adventures offers walking tours of the city’s spooky side.

But for those who love the great outdoors, Winter Garden has no bigger draw than the West Orange Trail, a paved, bucolic pathway that stretches 20.8 miles to Apopka in the north. With gorgeous scenery and ample amenities, including playground equipment for kids, the trail is perfect for hiking and biking. Didn’t bring a bicycle with you? Check out Winter Garden’s West Orange Trail Bikes & Blades Co., which offers bike rentals for adults and children, and even trailers for kids who are too young to pedal.

Learn more: Orlando Ecotourism

Top