Here at Oakland Park, we feel very fortunate to call Winter Garden our home. Here, both residents and visitors alike can enjoy the town’s unique blend of shopping, dining, local events, art, parks and—most importantly—people! Downtown Winter Garden is a historic district with lasting traditions, and now that the holiday season is in full swing, there are even more ways to enjoy what’s right in your backyard. To make it even easier for you, we’ve put together a list of several ways you and your loved ones can enjoy all that Winter Garden has to offer this time of year. Think: hot chocolate, meet-and-greets with Santa Claus, live music, creative workshops and more—all with the beautiful backdrop of twinkling lights, a towering Christmas tree and festive holiday décor.
Save the Date
It will be impossible to miss the plethora of holiday festivities taking place in Downtown Winter Garden on December 3rd. This full day of fun commences at 10am with the annual Winter Garden Christmas Parade, a long-standing tradition that is sure to bring delight to every spectator. As you watch the floats pass by, keep an eye out for Santa too! After the parade, Historic Downtown Winter Garden turns into the pedestrian-only Christmas Market on Plant St. Between the market itself and a plethora of local businesses, this event is a great opportunity to get a head start on your Christmas shopping—plus, without cars or traffic, you can enjoy the decorated streets and holiday music in peace. To finish out the day, make sure to stick around for the 10th Annual Christmas Golf Cart Parade, an amazing sight of elaborately decorated golf carts making their way through historic downtown.
At this year’s Holiday Boutique Stroll, you can find unique Christmas gifts for everyone on your list—just in time for the holidays! This family-friendly event, which will be taking place on December 8th from 5-8pm, is free to attend and will feature light refreshments, in-store raffles, indoor and outdoor specials, promotions and more! Plus, if you make a purchase at a participating store, you’ll be entered into The Grand Prize Raffle: a gift basket worth over $400! As you browse through the seasonal merchandise, you’ll also get to enjoy the enchanting decorations, colorful light displays and holiday music in the air.
All Month Long
Throughout the month of December, “Fridays on the Plaza” will give you numerous opportunities to get in the holiday spirit. Centennial Plaza’s weekly live music series will get a holiday twist on select Friday nights, so get ready to sing along to your favorite holiday tunes! The first Friday of the month also marks the 35th Annual Light Up Winter Garden tree lighting, to be followed by “A Big Band Christmas” concert. As you enjoy the music, you can also bring your kids over to Main Street Wonderland, which will feature a snow slide and 22 tons of “snow”.
The Winter Garden Fire Rescue Annual Santa Run brings Santa and his sleigh of “elves” (firefighters, police and city staff) through several neighborhoods within city limits. This moving parade takes place throughout the entire month leading up to Christmas, and is a fun way to spread holiday music, treats and good cheer.
While the Winter Garden Farmer’s Market is a recurring event, the month of December will bring additional vendors and festive surprises that you’re sure to enjoy. This award-winning hometown market is a community staple and features over 100 vendors—plus a complimentary KidZone full of hands-on activities and family-friendly games! In addition to locally sourced fresh produce and flowers, you’ll find holiday plants and wreaths, seasonal decorations and artisan food. The market runs every Saturday from 8am to 1pm at City Pavilion, and on December 10th and 17th Santa will make an appearance at “A Very Merry Farmer’s Market” from 9am to 12pm. Bring your Christmas wish list!