Top 10 Ideas for a Romantic Winter Garden Date Night

SPONSORED — Itching to get out of the house? Now is the ideal time to discover–or rediscover–the charm of historic Downtown Winter Garden. This walkable downtown is one of our go-to locales for a memorable date with plenty of places to dine, explore and shop in the fresh air. Plus, the city recently launched a brand new website along with official Facebook and Instagram pages highlighting the latest happenings. From expanded outdoor seating and festive events to an award-winning multi-use trail and weekly farmers market, challenge yourself to try all of these top 10 ideas for a Winter Garden date this fall.

1. Dine al fresco

The fall weather is ideal for outdoor dining. With Downtown Winter Garden's expanded patio seating, there is no better time to dine al fresco. Umbrella tables dot the historic streets of Downtown, including expansions into parking areas and the picturesque Centennial Plaza. Downtown’s extensive outdoor dining space, including hanging swing benches, provides an abundance of al fresco options to soak up the sunshine and historic charm in the fresh air.

Make sure to also stroll over to Plant Street Market, where you'll find a huge patio outside and a handful of vendors inside, including Crooked Can Brewery. Hunger Street Tacos will be joining the lineup of food vendors soon!

Centennial Plaza expanded patio seating | Image credit: City of Winter Garden

2. Shop Small Businesses

You'll find a host of unique, locally-owned boutiques and shops throughout the walkable downtown area. Peruse the shops to discover new favorites, support local business owners and take home one of a kind creations. It's also a great opportunity to start dropping Christmas gift hints to your partner (wink wink).

It's especially fun to align your shopping with one of the city's holiday and shop small events. A number of year-end activities are already planned, such as the Small Business Saturday Sidewalk Sale (November 28) and Holiday Boutique Stroll & Sale (December 10). You can also look forward to month-long Tis the Season programming in December to create holiday memories.

Reference the events calendar for a full list of upcoming happenings.

3. Grab a to-go feast for an outdoor picnic

Fall is the perfect time for an outdoor picnic with takeout from your favorite local Winter Garden restaurant! With the complimentary Downtown Winter Garden Curbside Program, order take-out from eateries and Downtown Ambassadors will deliver your meal right to the comfort and safety of your vehicle. Curbside deliveries from retail shops are also available. There are ample places to have an outdoor picnic downtown – the lawn at the pavilion makes a great picnic spot.

Get the full scoop on this Winter Garden date option here.

4. Explore Old Florida

Winter Garden is close to the shores of scenic Lake Apopka. For an outdoorsy Winter Garden date, head to Newton Park to catch a sunset over the lake. Stroll hand in hand across the park's over-the-water bridge for extra romance. This park offers a nature-filled retreat into Old Florida with all of the amenities of a charming downtown nearby. Or, explore the lush vegetation at Tucker Ranch Recreational Park and Nature Preserve. 

Winter Park date ideas - Newton Park
Image credit: City of Winter Garden

5. Do a bistro double date with friends

Small cafes and cozy bistros comprise part of Downtown Winter Garden's dining scene. Meet up with your quarantine squad for an outdoor happy hour, brunch, lunch or breakfast double date. Try Rosallie for a French cafe experience complete with coffee and pastries, or do brunch at Urban Flats. Delicious sandwiches served in a laid back atmosphere can be found at The Deli Downtown and Melts on Main. 

Check out all of downtown's dining and drinking options here.

6. Visit a cultural venue

Spark conversation and learn something new on a history or art-inspired date. You can brush up on Winter Garden history at the Winter Garden Historical Museum, which also hosts tours on foot and by bike. Get in touch with your inner kid at the Central Florida Railway Museum (it's free to visit) or see the latest exhibition at SOBO Art Gallery. Garden Theatre hosts live plays, interactive and classic movies, concerts and more each month.

7. Snap a couples selfie

From colorful murals to iconic landmarks, Downtown’s historic charm is the perfect backdrop for taking photos and selfies together. Snap a new photo on a swing in Centennial Plaza, pose in front of the Clock Tower, or take a selfie in front of one of the unique murals. You'll find the below mural (painted by artist @pjsvejda) on S Boyd St, just off of Plant Street.

Winter Garden murals
Image credit: Stephanie Patterson

8. Peruse the award-winning Winter Garden Farmers Market

Find local produce, colorful floral bouquets, fresh pasta, handmade goods and so much more at the Winter Garden Farmers Market each Saturday morning from 8am-1pm. Free parking is available in the parking garage and along the street. Consider picking up ingredients to make a meal at home together. This weekly market has been repeatedly ranked best in the nation and state by American Farmland Trust. The market takes place at 104 S. Lakeview Ave. 

Find out more about this local market in our Guide to the Winter Garden Farmers Market.

9. Relax in downtown's outdoor living room

Centennial Plaza is the heartbeat of Downtown Winter Garden. This cozy (and pet-friendly!) plaza features inviting porch swings, a picturesque fountain and extended patio seating for diners. The plaza's gazebo acts as the main stage for periodic live music performances. It's the ideal place to stop and rest for awhile before resuming your downtown explorations.

Image credit: City of Winter Garden

10. Hit the West Orange Trail

Bikers, walkers, joggers and more will love the 22-mile paved West Orange Trail, which conveniently passes through the center of Downtown Winter Garden. Plan a Winter Garden date with outdoor activity in mind, setting out on foot for a romantic walk or by renting bikes to cruise around on two wheels. Winter Garden Wheel Works rents bikes from the downtown trailhead just outside of town. 

A few of our recommended stops along the trail include the butterfly garden, Oakland Park (walk the mulched trail around the water) and the Oakland Nature Preserve.


We were compensated to write this post…
We are committed to providing you with valuable content that informs and inspires you…
We are clear that all of our content, including our sponsored content, gives value to our readers.
Our commitment as a for-profit website is to marry total transparency with superior, locally-created content. If you ever feel we fall short in that commitment, please let us know.

Learn more about advertising with us here.

Feature image credit: Downtown Winter Garden