Orlando is composed of many Main Street Districts, but Mills 50 captures the city through every element. The Mills 50 District comes to life at the intersection of Mills Avenue and Colonial Drive and includes all of the surrounding streets and businesses located along this stretch.
The area is filled with eclectic local businesses, each bringing their own uniqueness, while different cultures mix to provide the ultimate Orlando experience. Art of all types is welcomed and allowed to cultivate. The Mills 50 District is also filled with quality local eateries and shops who in turn support each other’s endeavors, adding character and a focus on community to lead the city by example. Better yet, the district is full of opportunities for a fun and budget-friendly date night.
Explore the Arts
The Mills 50 District is incredibly unique in that there is a form of art almost everywhere you turn. In addition to the Storm Drain Art Project and the Art Box Project, there are also over a dozen murals that decorate the walls of several buildings and establishments along Mills Avenue and connecting streets. Many business owners encourage artists to adorn their locations with murals for the city and all its visitors to enjoy. Some of these murals were created following the tragedy at Pulse Nightclub, as the LGBT Center of Central Florida and The Zebra Coalition reside in the district.
A must-do when in the area is to go on a mural tour on bike or foot. You will find art within walking and biking distance, it will be cost effective, and you'll see a completely different perspective of the city when you leave your car and explore.
Just outside of Mills 50, the Orlando Science Center, Orlando Museum of Art, and Mennello Museum of American Art round out the incredible abundance of art and creativity that fills this section of The City Beautiful. Admission to the Mennello Museum of Art is only $5, and with advance notice, you can arrange for a guided tour of the museum at no additional charge.
Get Active
The Orlando Urban Trail is approximately 3 miles long and takes you from Ivanhoe Village, through Mills 50, and all the way to Mead Gardens in Winter Park. If you'd like to rent a bike, there are several Juice Bike hubs in close proximity, at Orlando Health Village, and by Lil’ Indies. Bike rental is $8/hr. Along the way, you can stop and have a picnic at Loch Haven Park or simply enjoy the view of Lake Formosa, as this is a perfect place to catch one of our beautiful sunsets.
If you're looking for a couple's activity to clear your mind, catch a yoga class at Project 7 off of Virginia Ave. This beautiful studio offers classes with no commitment required and the single class drop in fee is $7. Make sure to arrive at least 15 minutes prior to class start as they are first-come, first-served.
Eats Under $30
Enjoy a meal under $30 for two at a local restaurant serving up delicious cheap eats! There is no shortage of quality affordable Eats in Mills 50. Local foodie favorites King Bao, Tako Cheena, and Black Rooster Taqueria are all within walking distance of each other (taco crawl, anyone?) serving up some of Orlando’s most sought-after bites.
King Bao offers a great special where you can select 2 bao and a drink for only $7, or 3 bao and a drink for $9. Try the Kickin’ Chicken, (Kimchi fried chicken, cucumber sriracha aioli and scallions) it has just enough kick and is packed with flavor.
Additionally, Black Bean Deli serves up reasonably priced and generously portioned Cuban platters and a killer cafe con leche, while Lazy Moon Pizza’s giant slices delight hungry Orlandoans and grace Instagram feeds aplenty.
Eats Under $50
Dinner for two under $50 is not hard to do, and some of Orlando’s best dining options are housed in this melting pot of delicious food and varying cultures.
Pig Floyd’s Urban Barbakoa mixes Latin/American/Asian influences to create perfection on a plate. The term “barbakoa” in the name refers to the practice of slowly steaming meat overnight to ensure it retains moisture and tenderness. You can get maduros (fried sweet plantains) as a side to your pulled pork or rib platter, and by all means get the Grilled Mexican Street Corn, topped with chili-lime butter and cotija cheese.
The Strand uses fresh, seasonal ingredients so dishes change regularly and everything is made from scratch. They commit to supporting local farms such as Lake Meadow Naturals, Olde Hearth Bread Co, and Florida & Co. The Strand Burger and Buttermilk Chicken are fan favorites, as is their brunch menu. Heads up, brunch is offered at The Strand on Saturdays, as they are closed Sundays.
Drink Up
Visiting closer to happy hour? The Mills 50 district has several unique bars perfect for grabbing a drink after a long day. If you're looking to visit Orlando staples, head to St. Matthew's Tavern, and Will’s Pub/Lil’ Indies. St. Matthew’s has several weekly drink specials such as Margarita Mondays ($3 well margaritas) and Whiskey Wednesdays ($3 well whiskey and $5 Jack Daniels) as well as 80’s Funk, Freestyle and Top 40 music with DJ K1X Friday night.
Other local favorites include The Guesthouse, a gorgeous craft cocktail bar, and Ten10 Brewing Company is the district’s local brewery, but they are much more than just craft beer. They serve sandwiches and snacks, have a running club (beer is an excellent reward after a run, am I right?) and host donut Sundays. Mills 50 is also home to Florida’s only sustainable winery, Quantum Leap Winery. Their tasting room is open Tuesday-Saturday, and they also host several fun monthly events.
Attend an Event
Fun and affordable events are plentiful in the Mills 50 District. Quantum Leap Winery is a hub for fun monthly events incorporating wine. Wine Down is held the 2nd Friday of the month and features live music and food trucks from 7-10 pm. Wine, Cheese, and Chocolate Perfectly Paired is more expensive, but features four Peterbrooke Chocolate confections, four La Femme du Fromage cheeses, and five Quantum Leap Wines. Lastly, Cabernet and Namaste ($21/person) combines wine and a cool flow yoga class. Tickets to these events can be purchased via Quantum Leap’s website.
In addition to being one of the coolest bars and live music venues in Orlando, Will’s Pub now also hosts a Tasty Takeover brunch every 4th Sunday from 11-3pm. This food truck meetup that takes over the Milk District every Tuesday evening has now wandered over to the Mills 50 District along with delicious food options including Da Kine Poke, Bem Bom, and Voodoo Kitchen.
Support Local Makers
Shopping local for any kind of gift is easy as this area has plenty of local shops and co-ops. The District Market at Mills 50 is a co-op featuring over 20 artisans and provides many of these local makers their first brick and mortar location. You'll find everything from natural soaps, vintage clothing, and greeting cards to jewelry and a large selection of vegan grocery items. A few doors down is Remix, which has a large selection of new and used vinyl records, vintage record players, cameras, and more.
Happy Hour Hop
There are various happy hour specials you can take advantage of with your honey. Hawkers Asian Street Fare’s happy hour is Monday-Friday from 3-6pm where you'll enjoy craft beers and small plates for just $3 each. Hawker’s carries local beers from places such as Funky Buddha and Crooked Can and has gluten free food options.
In the mood for Nashville Hot Chicken Sliders or Crispy Mahi Tacos? Firebird’s Wood Fired Grill has bar bites and drink specials Monday-Friday from 4-7pm and Saturday-Sunday from 1-5pm. Seasonal craft cocktails, select glasses of wine and all draft beer are reduced.
The Brass Tap has happy hour specials ranging from $4 wines, select draughts and sangria to a selection of appetizers between $4-$6 Monday-Friday from 4-7pm. The Guesthouse offers cocktail happy hour daily from 4-8pm, featuring $3 Yuengling tall boys and 40% off their cocktail menu.
More Orlando Main Street District date night ideas:
- Ten Dates for Couples in Orlando's SoDo District
- 6 Romantic Itineraries for Date Night in Ivanhoe Village
- A Week of Wallet-Friendly Dates in Audubon Park
- 6 Things to do Every Sunday in Thornton Park
- 8 Dates for Couples in The Milk District
- 5 Itineraries for a Low Key Date in College Park
- 7 Date Itineraries in Orlando's Iconic Church Street District
All images by Arlene Laboy
Arlene Laboy is a professional brand photographer based out of Orlando, Florida. A wife and a mother, Arlene shares her love for adventuring around Florida and her professional work through her Instagram account, @arlenemlaboy. Find out more about Arlene here.