8 Date Nights in The Milk District

The Milk District is a diversely dynamic neighborhood for locals that has become a draw for the region and a must-stop for visitors to get to know the city, a hive of creativity and culture in the heart of Orlando. The District strives to lead the region as home to authentic cultural experiences, destination dining, live entertainment, outdoor activities, and an innovative workforce.

Another distinctive feature of the Milk District is the abundance of street art that decorates businesses and buildings, adding character, color, and in some cases healing to our city. Most notable is the Orlando Strong mural located outside of Se7en Bites. The mural was done by artists Luce Sky and HepsFury, and was completed just a few days following the tragedy that occurred at Pulse Nightclub last May. The mural is just one example of the sense of community this district displays every day.

To help you explore this wonderful district for date night, we've come up with nine fun itineraries for couples.

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1. Brunch at Se7en Bites & Pho Hoa Murals

Chef Trina Gregory has been cooking up southern comfort food in the Milk District for years; way before she was on Guy Fieri’s radar. From the delicious breakfast offerings such as biscuits and gravy to the more indulgent 7th Trimester (my favorite), Se7en Bites is perfect when you’re in the mood for comfort food.

After you’ve devoured what you can and grabbed a to-go box of scratch-made bakery selections, walk some of those calories off by checking out some of the amazing murals covering Pho Hoa’s walls and surroundings.

Related post: Orlando Murals + Menus: A Full Day Art and Food Itinerary


2. Food Trucks and Movies

So, you’re ready to have some fun but dinner is too predictable for date night. No worries! Put a spin on your usual dinner date by heading to Á La Cart, a mini food truck park and craft beer bar in one.

Besides the lineup of resident food trucks, the space hosts a weekly outdoor movie night every Monday featuring flicks running the gamut from throwbacks (like Top Gun) to beloved series (Harry Potter) and everything in between. Pick your food truck fare, a few beers, and settle in for a chill beginning to the week together.

Related post: Where to Watch Outdoor Movies in Orlando: Year-Round Guide

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Á La Cart Orlando

3. Brunch and Brews

Brunch is a go-to day date idea and the Milk District has got you covered. Head to Milkhouse where you can grab a coffee from Foxtail, some brunch bites from Swine & Sons, and finally some ice cream from Kelly's Homemade Ice Cream.

Continue your date across the street at Sideward Brewing, a local brewery with quality brews (try the Citra-Nelson New England IPA), a spacious outdoor patio, and a food menu featuring shareable snacks and sandwiches. The brewery is owned by Garrett Ward (Cask & Larder, Red Cypress Brewery), Mandy Protheroe (Redlight Redlight, Coppertail Brewing Co.), and Austin Ward (The Biltmore). 

Related post: 15+ Orlando Brunch Spots with Bottomless Mimosas

Kelly's Homemade Ice Cream
Kelly's Homemade Ice Cream | Image credit: Arlene Laboy

4. Tasty Takeover in the Milk District

Some of the best food you'll find in Orlando comes from our fleet of local food trucks. Tasty Takeover offers a bountiful selection when you’re looking for a delicious date night menu. Parked behind Etoile Boutique, this weekly food truck meetup is a nice change of pace from an ordinary date night.

Each food truck provides a different culinary experience than what you would normally find around the city. Frequent attendees include Red Panda Noodle, Over Rice, and Smokemade Meats, but the full lineup of trucks is updated weekly on Tasty Takeover's Facebook page.

After you’ve fueled up, stop in Etoile to see why they were voted Orlando Weekly’s Best Boutique. Their selection of vintage clothing and accessories can be purchased with a 10% discount offered to Tasty Takeover attendees.

Don't forget to stop into one of the neighborhood bars; you're welcome to bring in food to enjoy. Sip craft brews, kombucha, and wine-based cocktails at The Nook on Robinson before calling it a night.

Related post: Food Trucks and Pop-Ups Around Orlando

Image credit: The Nook on Robinson

5. Smoke & Donuts and Skateboarding

Smoke & Donuts is a nationally recognized barbecue & donuts restaurant and catering company
located in the heart of Orlando, Florida. What began as a locally-loved pop-up turned food truck
has since transformed into a city staple serving savory-smoked barbecue and sweet, handmade donuts.

Once you've had your fill of barbecue and donuts, grab your deck and head to Orlando Skate Park. This vast park has a variety of outdoor courses for skateboarders, from beginner to advanced levels. If skateboarding isn't your thing, it is still a great place for people watching and enjoying the great outdoors.

Related post: Over the Top Orlando Desserts to Blow Your Mind on Date Night

6. Catch a Live Show at The Plaza Live & Pom Pom’s Teahouse

The Plaza Live has been a Milk District (and Orlando) staple since before the area it calls home was even officially known as the Milk District. Built over 50 years ago as the city’s first 2-screen movie theater, it has evolved from a movie theater to one of the city’s best live venues hosting everything from comics to concerts.

After your show, head to Pom Pom's Teahouse & Sandwicheria; they're open til 11pm on Friday and Saturday nights.

Pom Pom’s Tea House specializes in unique sandwiches and extensive tea selections, and the must-try is Mama Ling Ling’s Thanksgiving Sandwich. It's as good as it sounds – turkey, Gouda, stuffing, ginger cranberry chutney, mashed potatoes, cream cheese, and a side of gravy to dip your bites in. The Spicy Turkey Mac n’ Chez is another fan favorite.

Added bonus: the restaurant is covered in vibrant colors and art from local artists that is available for purchase.

Related post: Small Live Music Venues in Central Florida for a Big Night Out

7. Games, Pool, and Drinks at Sportstown Billiards

Sportstown is cool for a variety of reasons, first being their vast selection of drinks; you’ll find a wide array of beer to choose from, including everything from IPAs to ciders. Where this bar differs is the addition of pool tables, board games, and arcade games to keep you and your date entertained while you drink your brews. Smoking is allowed so this bar can get pretty smoky, but it has a fun, laid-back atmosphere for a low-key date night. 

Ready for a bite? Conveniently located a few doors down is Gringos Locos, famous for their Double D's and equally awesome late hours.

Related post: Orlando Taco Spots That Will Impress Your Date

On the edge of the Milk District is Primrose Lanes. It's one of our favorite indoor activities in Orlando. This vibrant eatery is ideal for date night. It pays homage to this historic bowling alley, with a modern focus on elevated cocktails and delicious eats. Reservations for dining are not taken, but reserving a bowling lane in advance is highly encouraged.

bowling pin decor at primrose lanes in orlando
Primrose Lanes in Milk District – image by Dani Meyering

8. Good For You Date

Nothing will motivate you more than a workout partner. For this date you won't have to spend an hour getting ready; just throw on some joggers/leggings, your favorite big tank top, and head over to Orlando Power Yoga! If boot camp is more your style you can check out CrossFit Milk District.

Get that pre-workout boost beforehand by stopping in Juice Bar for a smoothie or juice and finish your workout by replenishing your body with food from one of the many shops in Market On South.

Related post: 30 Self-Care Ideas for Orlando Area Couples

9. Barley & Vine Biergarten

Day drinking is usually frowned upon, except when your date takes place at the Milk District’s first (and only) Biergarten. Barley & Vine offers 25 rotating craft beers on draft and 150 bottled craft beers which you can sip while relaxing on the lovely outdoor patio area. Specials include Barley Retro Saturdays ($3 selected craft beer cans and $1 off all wine), or  $15 all-you-can-drink mimosas on Sundays during their hangover brunch.

Hungry? Take a stroll a few blocks up the street to Stasio's Italian Deli & Market, an authentic Italian deli serving hearty sandwiches on homemade bread (made fresh daily), freshly-baked desserts, plus an assortment of Italian goods (pasta, meats, cheese, wine, olive oil!) to take home. 

Related post: A Beer Lover’s Guide to Breweries in Orlando

More Orlando Main Street District date night ideas:

All images by Arlene Laboy unless otherwise noted

Feature image mural artist: Joseph Starkweather