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Top 10 Holiday Events In & Around Longwood, FL

Todd Schroth

Todd Schroth, licensed Florida Real Estate Agent, has been investing in homes since 1995, as well as selling and listing throughout the Central Florid...

Todd Schroth, licensed Florida Real Estate Agent, has been investing in homes since 1995, as well as selling and listing throughout the Central Florid...

Feb 8 7 minutes read

Get into the Holiday Spirit with one of the fun local area events below. With a little something for everyone you’re sure to find the perfect activity to share in holiday cheer and maybe a beer. 

#10 Budweiser Clydesdales in Altamonte Springs

Sunday, December 11 at 4 PM - 6 PM. 

Cranes Roost Park, 274 Cranes Roost Blvd, Altamonte Springs, Florida 32701

The World Famous Budweiser Clydesdales are coming to Cranes Roost Park in Altamonte Springs FL on Sunday December 11th for a FREE TO THE PUBLIC showing! See the Full Hitch in all it's glory from 6-8pm and take a picture with the Clydesdales.

Wayne Densch Inc. the Seminole County+ Budweiser Distributor based out of Sanford FL was recently awarded the Anheuser Busch "Ambassadors of Excellence" Award, which is presented only to a select few distributors nationally each year. In honor of the award, Anheuser Busch has scheduled a weeklong visit to the WDI Market with stops also scheduled for Oviedo, Longwood, Sanford and Leesburg. Click here for more info. Click here for more info.

#9 Shop Local - Sweetwater-Wekiva Farmers Market

Every Sunday: 10AM-3PM

1000 Wekiva Springs Road Longwood, FL 32779

The Sweetwater Wekiva Farmers Market is comprised of local artisans and crafters that are devoted to bringing you and your family wholesome goods that will not be found in chain stores.  We are happy to bring the community together every week to fill your home with local goods, provide the neighborhood with services, and to rejuvenate the small-town notion that will allow our patrons to grow closer to one another. Join your neighbors every week to shop small in support of your local artisan vendors! 

#8 Breakfast with Santa

Saturday, December 10 at 8 AM - 11 AM

Longwood Hills Congregational Church, 1255 EE Williamson Rd, Longwood, Florida 32750

Come and enjoy ALL YOU CAN EAT pancake breakfast with Santa! *Kids Crafts* *Pictures with Santa* Don't forget your Christmas list and your appetite! Tickets are $5.00 for adults and $2.50 for children under 12. For more information contact Sharon at 407-491-7191. Click here to view the flyer.

#7 The Great Christmas Light Adventure for Kids

December 10 at 5:30 PM & December 11 at 7:30 PM

Green Meadows Petting Farm, 1368 S Poinciana Blvd, Kissimmee, Florida 34746

Get everyone in the car for a family fun day at Green Meadows Petting Farm. They will have de-LIGHT-ful themed light displays. Walk around and enjoy Winter Wonderland, Undersea Christmas, Santas from around the world, and Santa's Workshop. Warm up with hot chocolate and our homemade apple cider. Don't forget your golden ticket to ride the Jingle Bell Express Train!

#6 Santa Tuesday

Tuesday, December 13 at 6 PM - 8 PM

Uptown Altamonte, 274 Cranes Roost Blvd, Altamonte Springs, Florida 32701

Bring your wish list to meet Santa and Mrs. Claus under the tower. Bring your camera for free photos with the Clauses. Food and beverages available for purchase. No pets.

#5 Home Alone Holiday Movie Night

Thursday, December 15 at 7 PM - 9 PM

Uptown Altamonte, 274 Cranes Roost Blvd, Altamonte Springs, Florida 32701

Watch free holiday movies on the Plaza lawn brought to you by Florida Hospital Altamonte. Food and beverages are available for purchase. The December 15th showing will feature a holiday favorite “Home Alone.”

#4 2nd Annual Ugly Sweater Party

Friday, December 16 at 7 PM - 10 PM

Red Cypress Brewery, 855 E State Road 434, Winter Springs, Florida 32708

Tis the season for ugly sweaters! Bring in the holiday season in your tackiest apparel! Join Red Cypress Brewery in the taproom for their 2nd Annual Ugly Sweater Party. Daydream Pizza will be serving up their amazing pizzas from 6pm to 9pm and Brian Smalley will be providing live music at 7pm! Prizes will be awarded to the three ugliest sweaters. Added bonus: they will be releasing a special beer that evening!

#3 Snow Fest

Saturday, December 17 at 2 PM - 6 PM

RDV Sportsplex Ice Den, 8701 Maitland Summit Blvd, Maitland, Florida 32810

Enjoy Central Florida’s Favorite Holiday Family Event. During SNOW FEST, attendees can enjoy ice skating, playing in REAL snow, a snow slide for kids, bounce houses, live DJs, meet the Ice Queen and Princess, and get their faces painted. The cost is $15 for Ages 3 and up. Get more info by clicking here.

#2 Ugly Sweater Holiday Market Party w/ Beer & Cookie Pairing

Saturday, December 17 at 4 PM - 9 PM

Hourglass Brewing, 480 S Ronald Reagan Blvd, Longwood, Florida 32750

Wear an ugly sweater and receive your first Hourglass draft for half the price! Hourglass is also an official Toys for Tots drop-off location; bring in a toy to donate and provide a child in need with something special for Christmas!

The party starts are 4pm: Beer Flight and Cookie pairing with five holiday-themed beers, including our new Tummy Kisses Oatmeal Raisin Blonde Ale. 4-8pm: Holiday pop-up shops from local artisans and small businesses. Get your last minute gifts (or treat yourself). 6-9pm: UCF Jazz Quartet band playing a special holiday performance--you won't want to miss it!  9:30 pm: Rounding out the party will be the very talented Sarah Purser with a set of holiday standards and original compositions!

#1 Annual Wekiva Island Boat Parade

Saturday, December 17th from 5 PM to 10 PM

Wekiva Island, 1014 Miami Springs Dr, Longwood, Florida 32779

The second annual boat parade on the Wekiva River is taking place on Saturday, December 17th at Wekiva Island. Come out and watch the parade and enjoy the Winter Wonderland or become a patient in the boat parade by filling out the registration link on their website. Arrive early and bring your own chairs and blankets to grab your seat and enjoy food and drinks from the Without a Paddle Café. Carpooling and UBER are strongly encouraged as parking will be limited. Show proof of your UBER receipt and get $3 off your bar tab. 

Other activates happening: Free Gift Wrapping Noon-5pm; Santa Visits 2 - 7pm; Evening Snow Flurries at 6pm; Lighted Stiltwalkers- 7pm-9pm; Live Remote with 103.1 The Wolf 7pm - 9pm; there will also be will snow flurries, Christmas lights and decorations galore!

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