7 Quintessential Dates at Plant Street Market (VIDEO)

Plant Street Market Winter Garden

Plant Street Market is a one-stop shop for date night: delicious eats, a bustling brewery, easy access to the 22-mile paved West Orange Trail, and a killer outdoor patio.

Located 25 minutes from Orlando in charming downtown Winter Garden, the market houses over a dozen local vendors. So if you’re feeling like sushi but your date is craving pizza, this may be the answer to your “where to go” woes. The activities don’t stop at food; you can also partake in outdoor yoga, eat your eay through a food tour, or attend events and festivals held at the market.

There’s no wrong way to have a date at the market, but below you’ll find a few itineraries for easy planning.

Pizza + Brews

It makes sense to start with my personal favorite Plant Street Market date combo: pizza and beer. After a 4.5-mile bike ride from West Orange Bikes & Blades to the market, my boyfriend, John, and I are always ready to refuel before heading back.

Start out by heading to Michael’s Ali Coal-Fired Pizza to pick up a freshly made pie to share. Choose from one of six pies from the menu (the Brooklyn is delicious!) for $13-$16, or create your own for $11 plus $1.50 per topping. A cold pint of beer from Crooked Can Brewing Company, just steps away, accompanies the carb-coma-inducing meal perfectly. Signature beers include the Cloud Chaser Hefeweizen and High Stepper IPA.

Food Tour

What better way to get a taste of the market than during an organized food tour? Husband and wife team John and Jamie Baylor fell in love with Winter Garden while on date night, eventually moving to the area and launching Winter Garden Food Tours in 2017. Not only are they an adorable couple that is fun to spend time with, they’ve also created a handful of great tours that showcase all Winter Garden has to offer foodies.

The signature Plant Street Dinner Tour (Thursdays at 6pm) will take you on a culinary adventure through the market and beyond, providing the perfect introduction to the area. The brunch tour also features stops inside the market, with the 2pm tour culminating in a brewery tour at Crooked Can.

Winter Garden Food Tours
Winter Garden Food Tours. Photo by Melissa Ann Photography

Afternoon Tea

Feeling classy? AntiquiTEAs, owned by tea lover Marc Baudendistel, is your go-to spot for afternoon tea. Select from over 30 varieties of loose leaf tea, including seasonally-inspired selections, for a hot (or cold) afternoon treat to sip. Stop by to sample the signature iced tea of the day, or take a seat for daily tea service. A pot of tea costs $5.95, while tea and crumpets are $8.95.

For the ultimate girls’ day or double date, contact Marc to book a private tea party. Couples will enjoy the Base Tea service ($12.95/person), which includes two pots of tea and assorted sweets to share. Full Tea ($25.95/person) is available for groups of four or more and includes a pot of tea for each guest plus mixed greens, scones and cream, tea sandwiches served on vegetable rounds, plus assorted sweets and fruit.

Tea party at Plant Street Market with AntiquiTEAs
Image credit: AntiquiTEAs

Yoga and Beer

Balance fitness and indulgence while improving your balance during a weekly outdoor yoga class at Crooked Can. This yoga class comes with extra incentive to see your workout through to the end: a free beer afterward.

Aptly named, Hair of the Downward Dog takes place on the silo lawn every Saturday at 11am. The class is open to yogis of all levels and lasts for one hour. Afterwards, you’ll get your pick of a 13oz or 16oz beer from the brewery. The cost of the class is $10.

FYI: you can still attend even if you aren’t 21. You won’t get a beer (obviously) but the class price drops to $5.

Dessert Hop

Instead of choosing one dessert after your meal, choose three with a dessert hop. The newest to arrive at the market, Sir Benji’s Donuts crafts fresh, made to order mini donuts. This husband and wife owned shop offers crazy fun flavors like apple cider moonshine, bourbon bacon, churro, and the French Quarter, a beignet-inspired doughnut. Donuts are $6/dozen (pick two flavors) or $4/half dozen.

Continue your sweets journey with a stop at David Ramirez Chocolates across the way. Feast your eyes on the chocolate fountain before ordering an assortment of macarons ($2.05 each or dipped for $2.50) and almost too pretty to eat chocolates ($1.80 each).

Make your final stop at Paleteria Original, a cart serving up handcrafted paletas (ice pops made with fresh fruits and ingredients). Cool down with flavors like Strawberry and Nutella, Double Dulce de Leche, Oreo, and Passion Fruit.

Progressive Dinner

Start with some nibbles of sushi at Jodo Sushi, or some loaded fries from This Little Piggy topped with cheese sauce, BBQ sauce, pulled pork, and scallions. You’ve got tons of options for entrees, including BBQ at This Little Piggy, coal-fired pizza at Michael’s Ali Coal Fired Pizza, custom mac n’ cheese from MAC’d Out, or a meaty sandwich from The Local Butcher and Market.

After your main dish, treat yourself to Gezellig cookies (sold at AntiquiTeas or in ice cream sandwich form at The Cookery), or keep up the progressive experience by completing the dessert hop above.

MAC'd out Plant Street Market
MAC’d Out

Healthy Eats

I know I’ve been droning on about BBQ and pizza, but Plant Street Market has healthier options, too! Press’d Juice Bar & Kitchen serves some of the prettiest acai and pitaya bowls around town, topped with granola, coconut, and fresh seasonal fruits. These bowls are great fuel for a bike ride or walk around town.

Aside from acai bowls, they also serve fresh smoothies, cold pressed juice, salads, plant-based wraps, and mini elixirs, like the flu shot (essential this time of year). Pair lunch or dinner with a bike ride and you’ve got a fitness-friendly date night.


The market is busy on weekends, especially when the weather is nice. Arrive early or visit during a weekday if you’re looking for a more subdued atmosphere.

Renting bikes? From West Orange Bikes & Blades, expect a 45-minute ride at a relaxed pace on mostly flat paved terrain. Rentals are due back at 5pm, so this works best for an afternoon visit. Alternatively, you can rent bikes from Winter Garden Wheel Works’ rental station a little over a half a mile from the market (15-minute walk).

Plant Street Market
426 W Plant St
Winter Garden, FL
Monday – Saturday 10am-7pm
Sunday 11am-6pm


Each vendor has independent hours. Some food spots close as early as 6pm, with others staying open late until 9 or 11pm. Plan accordingly if you’re visiting for an evening date or arriving earlier in the morning.

Michael’s Ali Coal-Fired Pizza
Sunday-Monday: 11am-8pm
Tuesday-Thursday: 11am-9pm
Friday-Saturday: 11am-11pm

Crooked Can Brewing Company
Sunday-Thursday: 11am-11pm
Friday-Saturday: 11am-1am

Monday-Tuesday: Closed
Wednesday: 10am-4pm
Thursday-Saturday: 10am-7pm
Sunday: 11am-6pm

Sir Benji’s Donuts
Thursday-Saturday: 10am-7pm
Sunday: 11am-6pm

David Ramirez Chocolates
Monday-Thursday: 11am-7pm
Friday: 11am-9pm
Saturday: 10am-9pm
Sunday: 11am-6pm

Paleteria Original
Monday-Saturday 11am-9pm
Sunday: 11am-7pm

Press’d Juice Bar & Kitchen
Monday: 8:30am-4pm
Tuesday-Saturday: 8:30am-7pm
Sunday: 11am-6pm

Jodo Sushi
Monday-Thursday: 11am-9pm
Friday-Saturday: 11am-11pm
Sunday: 11am-7pm

This Little Piggy
Monday-Tuesday: 12pm-8pm
Wednesday-Thursday: 12pm-9pm
Friday: 12pm-10pm
Saturday: 11am-10pm
Sunday: 11am-8pm

MAC’d Out
Monday: 11am-7pm
Tuesday-Thursday: 11am-8pm
Friday: 11am-9pm
Saturday: 11am-9pm
Sunday: 12pm-7pm

The Local Butcher and Market
Monday-Saturday: 9am-7pm
Sunday: 11am-6pm

Florida food and travel photographer and writer Stephanie Patterson

About the Author/Photographer:
Stephanie Patterson is the managing editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at www.spattersonphotography.com and www.traveltasteclick.com.


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