Top 10 Ways to Celebrate 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.

1. Shop for Local Gifts at TWO Holiday Shopping Events

Downtown Winter Garden is full of unique shops, offering you the perfect opportunity to discover one-of-a-kind gifts while shopping local this holiday season. In November, Downtown Winter Garden is hosting a citywide Small Business Saturday Downtown Sidewalk Sale on November 27, 2021. This shopping event coincides with the weekly Winter Garden Farmers Market (Saturdays from 8am-1pm). Stick around for a free holiday movie under the stars beginning at 7:10pm at the Downtown Pavillion. 
In December, save the date for the annual Holiday Boutique Stroll on December 9, 2021 from 5-8pm. Visit participating boutiques for light refreshments, raffles, deals and seasonal merchandise. Plan to stroll around downtown after shopping to marvel at the festive decorations.

2. Take a Holiday Horse Drawn Carriage Tour

There's simply no more romantic way to take in Winter Garden's twinkling lights than on a holiday horse drawn carriage tour. SOUL Haven Ranch offers this magical experience throughout December for $85. The carriage fits up to four adults, or two adults and three kids. Available dates are December 4, 10, 11, 17-19, 22-24, and 26-30 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.

SOUL Haven Ranch Holiday Horse Drawn Carriage Tours

3. See a Holiday Movie

Kick of the holidays early with a FREE Moonlight Movie Thanksgiving weekend. Head to the Downtown Pavillion on Saturday, November 27, 2021 for a free outdoor screening of The Polar Express. Pre-movie activities begin at 5:30pm followed by the movie at 7:10pm. 
Additionally, Garden Theatre hosts regular Interactive and Classic movie nights. On December 5, 2021, enjoy an interactive movie experience featuring The Muppet Christmas Carol. Tickets are $15 and include the movie plus pre-show activities.

4. 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, 10, 11, 12, 17, 18, 19, and 23, 2021.

Merry Winter Garden Light Show

5. Listen to live holiday music

Get in the holiday spirit and sing along to your favorite holiday tunes at Centennial Plaza select Friday evenings in December. Winter Garden's weekly Friday night live music series will get a holiday twist with live entertainment from Roots & Rosin on December 10 and The Caroling Company on December 17. The fun begins at 7pm and admission is free.
Holiday street performers and jugglers will take to the streets on Friday and Saturday evenings December 3 – 18, 2021 from 6-9pm for more festive fun.
Lastly, ring in the new year on December 31, 2021 with live jazz music from 8:30pm – 12:30am at Pilars. Dance to live jazz music all night, and fuel up in between with food available from local restaurant Market to Table.

6. Find goodies at the Merry Winter Garden Farmers Market

On December 4, 11 and 18, 2021 from 8am-1pm, find unique gifts, holiday decor, and seasonal food at the Winter Garden Farmers Market. We love checking out this local market weekly, which now boasts 100+ vendors — here's our guide
Once you've stocked up, continue your shopping along Plant Street. The newest additions are Apricot Lane Boutique, LiveTrends Boutique, Main House Market, and Polka Dotz.

7. 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. Continue your holiday date by making your way through the winding Winter Wonderland Maze at City Hall, stopping to pose for pictures at the holiday vignettes along the way.
While you explore, sing along to your favorite holiday tunes with classic holiday songs filling the air through the City’s sound system. And see how many of the city's holiday-themed photo locations you can find along the way!
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.

Centennial Plaza Christmas Tree

8. Sip on Seasonal Coffee Creations

Stop into one of Downtown Winter Garden's coffee shops, restaurants and bakeries to sip holiday hot cocoa, seasonal beverages and seasonal treats. Foxtail Coffee Co. (276 W Plant Street) will join the lineup of Downtown Winter Garden coffee shops just in time for the holidays.

9. 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 a holiday mural wall. Find it on the side of Doxology (49 S Main St) for the entire month of December.
You'll also find multiple holiday-themed photo vignettes around town, including within the city's Winter Wonderland Maze at City Hall.

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 movie in December, you can also score tickets to Big, the Musical. See it on stage through December 19, 2021. Garden Theatre will also host a Holiday Concert performed by the Garden Choir on December 12, 2021.


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All images courtesy of City of Winter Garden