A Date Night Bucket List for Celebrating the Holidays in Winter Garden

A Date Night Bucket List for Celebrating the Holidays in Winter Garden

SPONSORED – Looking for the perfect place to make new holiday memories this season? Celebrating the holidays in Winter Garden always tops our list each December. And this year, the city is looking especially merry and bright thanks to hundreds of twinkling lights and a large Christmas tree adorning the central plaza, plus a lineup of festive events. To help you live out your own holiday romance, we’ve put together this bucket list of the best date night-approved holiday dates in Winter Garden.

PS: Bookmark this holiday guide as a handy reference during your visit.

1. Take a Holiday Horse Drawn Carriage Tour

There’s simply no more romantic way to take in Winter Garden’s seasonal decor and holiday lights than on a holiday horse drawn carriage tour. SOUL Haven Ranch offers this magical experience throughout December for $65. The carriage fits up to four adults, or two adults and three kids. Available dates are December 4, 5, 11, 12, 18, 19, 26, 27, 28, 29, and 30, 2020 between 5:30 and 9:30pm. Tours begin at the Winter Garden Downtown Pavillion (104 S Lakeview Ave).

Reservations are required and can be booked online or by calling 407-509-1981.

SOUL Haven Ranch Holiday Horse Drawn Carriage Tours

2. Watch the Merry Winter Garden Light Show

Head to Winter Garden City Hall for a special FREE light show projected on the building select nights in December. Between 6-9pm, the front facade of the building is transformed into a dazzling display of holiday lights and projections synchronized to holiday music. See it for yourself December 4, 5, 11, 12, 13, 18 and 19, 2020. 

Merry Winter Garden Light Show

3. Shop for Unique Finds at the Holiday Boutique Stroll & Sale

Shop local and discover new-to-you boutiques and shops during the Holiday Boutique Stroll & Sale on December 10, 2020. This outdoor sidewalk sale includes great deals and seasonal merchandise from local retailers. You can also take advantage of Downtown Winter Garden’s complimentary curbside program which includes contact-free delivery of purchases from shops and restaurants straight to your car by a downtown ambassador. Stick around for a live performance from a quartet of traditional Dickens carolers from 5-7pm at the Centennial Plaza.

4. See a Holiday Movie at Garden Theatre

Garden Theatre hosts regular Interactive and Classic movie nights and this December you can catch two holiday classics. First up is a screening of the holiday classic It’s a Wonderful Life on December 6. On December 13, you can be a part of the movie during a screening of The Muppet Christmas Carol. This interactive movie experience includes pre-show games, trivia, and costume contests hosted by live actors. Tickets are $15 and seats are socially distanced to keep you safe.

5. Enjoy a live Performance from Dickens Carolers

Get in the holiday spirit with special live performances from a quartet of Dickens-era carolers. Sing along to your favorite holiday tunes at Centennial Plaza. Performance dates are Thursday, December 10 from 5-7pm and Saturday, December 19 from 6:30-8:30pm. Admission is free.

Free Holiday Events in Orlando - Dickens Carolers in Downtown Winter Garden
Image credit: City of Winter Garden

6. Find goodies at the Merry Winter Garden Farmers Market

Every Saturday in December from 8am-1pm, find flowers and wreaths, holiday plants, fresh produce and artisan food at the Winter Garden Farmers Market. We love checking out this local market weekly — here’s our guide.

Once you’ve stocked up, continue your shopping along Plant Street where something new always seems to be popping up. The latest addition? A cozy new outpost for independent bookstore Writer’s Block Bookstore.

7. Snap a Selfie in front of Holiday Photo Ops

Still searching for the perfect spot to take a couples selfie for this year’s holiday cards? Downtown Winter Garden is a festive wonderland complete with twinkling lights, a huge Christmas tree and–new this year–a painted holiday mural wall. You’ll also find multiple holiday-themed photo vignettes around town.

This special mural wall is a collaboration between the city and The Winter Garden Art Association. The mural was designed by Artist Jenn Sayler and recreated by Rachel Ross. Find it on the side of Doxology (49 S Main St) for the entire month of December.

Holidays in Winter Garden mural wall
Holiday mural wall

8. Feast on Seasonal Treats

Stop into one of Downtown Winter Garden’s coffee shops (we love Axum and Rosallie!), restaurants and shops to sip holiday hot cocoa, seasonal beverages and seasonal treats. Axum and Rosallie typically offer special holiday drinks to celebrate the season, and you can stock up on seasonal sweets at places like Way Chocolate.

9. Check out the Festive Decorations

It’s impossible to miss the towering Christmas tree in Centennial Plaza, along with holiday lights all along Plant Street. Bring your bikes or set out on foot to wander through the surrounding neighborhood for a self-guided holiday lights tour sure to put a smile on your face.

While you walk, sing along to your favorite holiday tunes with classic holiday songs filling the air through the City’s sound system.

Centennial Plaza Christmas Tree

10. Have a Holiday Dinner + Theatre Date

Give your next dinner and a show date a holiday twist! Winter Garden has expanded patio seating available at most downtown restaurants, perfect for grabbing a bite outdoors before heading to Garden Theatre for a show. Plus, you’ll get to soak up all the holiday ambiance while you dine. Make reservations and find new restaurants to check out here.

Besides Garden Theatre’s interactive and classic movies in December, you can also score tickets to Roald Dahl’s Matilda the Musical. See it on stage through December 20, 2020.


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All images courtesy of City of Winter Garden

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