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The Best Holiday Events in Orlando

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Thanksgiving may be over now, but the holiday season is in full swing. We’ve made our list, checked it twice, and have found some of the best things to do in Orlando that yule love. From themed bar crawls to a holiday boat parade, this list is the one you’ll need to check twice to make sure you don’t miss anything.

Whether you’re naughty or nice, Orlando has something for everyone to enjoy. So grab some hot cocoa and gather around the (unnecessary) fire.

Have you been looking for a great way to kick off your holiday season? This event is a perfect way to get all of the holiday goodness in one night. From ice skating, to live performances, and free games for the kiddos, you will definitely want to deck the halls after this night. The holiday season is all about having fun with family and there are so many ways to have fun at this celebration. You will even get to see the annual Longwood tree lighting ceremony! If that doesn’t get you excited to celebrate the holidays, we don’t know what will.

Event Details
🗓 DEC 7TH | 6:00PM–9:00 PM
📍 Reiter Park

On the first day of Christmas, our best friend gave to ussssss…one awesome bar crawl to get you into the spirit of the season. Gather your loved ones close and head downtown for a night that you might not remember. You’ll get the opportunity to experience 12 different bars throughout the night with drink specials for all. In the spirit of giving, you can also purchase a Santa hat to wear throughout the festivities. All of the proceeds from the hats will go towards the HOPE foundation, whose mission is to help reduce and prevent homelessness in Central Florida by helping individuals become self-sufficient through housing, outreach, prevention, and education. This is one event that will keep you feeling jolly throughout the night!

Event Details
🗓 DEC 7 | 8PM–1AM
📍 Wall Street Plaza
🎟 $$

If you’re looking for something a little more traditional, check out Winter Spark at Baldwin Park. This family-friendly event features a holiday market in the afternoon followed by a holiday parade when the sun goes down. There will be vendors, food trucks, and a chance to take pictures with Mr. and Mrs. Claus. This event happens right in the center of the Baldwin Park area and is sure to light up your holiday season. You can even buy some last minute gifts for all of your loved ones as you enjoy the festivities.

Event Details
🗓 DEC 8 | 4PM–8PM
📍 Baldwin Park
📸 Baldwin Park Events

If you’re looking for something that screams “Florida,” head on over to Winter Park to experience their annual Holiday Boat Parade. Participants will be decking their boats out in holiday cheer and you will be able to watch them show off their decorations. You can even make donations during the event to benefit the Food Pantries at Winter Park High School and Killarney Elementary School. This event is great for the whole family, so come out and see who takes home the coveted Best Boat award!

Event Details
🗓 DEC 15 | 3:30PM–7:30PM
📍 Rollins College

If you’re looking for a night that you won’t soon forget, come take a ride on THE POLAR EXPRESS™ Train Ride Orlando. Board the train and travel all the way to the North Pole as you are served hot cocoa and treated to the dancing chefs. The classic movie will come alive around you and truly usher in the Christmas spirit. You can even wear your pajamas on board…that alone makes us want to be the first in line. So grab your golden ticket and hop aboard! They already had us at “hot cocoa.”

Event Details
🗓 NOW–DEC 30TH | 6:30PM–7:40PM
📍 Mount Dora Plaza
🎟 $$
📸 The Polar Express

There are so many more amazing holiday events happening this year:

The Nutcracker

Christmas Cookie Run

40th Annual Christmas in the Park

Winter Garden Christmas Parade

Celebrating Christmas at Lake Eola

There are so many holly-jolly things to enjoy in Orlando this holiday season! Search #YuleNation in the UNATION APP or on the website to find the best events happening this season. Don’t forget to tag #StuffToDoinOrlando so that we can keep up with the festivities. We can’t wait to celebrate with you!

Happy Holidays, Love UNATION ❤️


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Amanda Orling

Amanda Orling

Amanda is the City Manager for UNATION and author of the  Stuff to Do in Orlando blog. For more insight on the best events and things to do in the Orlando area, download the UNATION app and follow @StufftoDoinOrlando on Instagram and Facebook.

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