Dust off your ugly seater and grab your Santa hat. This weekend is full of festive holiday events in Orlando everyone can enjoy. Whether you're a couple looking for the perfect date night, or the bar goer looking to solidify their spot on the naughty list, our list of things to do in Orlando are sure to warm up your weekend.


Dos XX-Mas Block Party on Wall Street

When: Sat. Dec. 15th | 9PM
Where:  Wall Street Plaza

Wall Street doesn't always have a Christmas themed block party, but when they do it’s Dos XX-Mas! The most interesting Wall Street block party is back Saturday, December 15th! Participate in the Tortilla Toss competition to win prizes like free beer and t-shirts.

Read More: The Most Interesting Holiday Block Party In The World Is On Wall Street Plaza

Orlando Santapalooza 2018

When: Fri. Dec. 14th | 8 PM
Where: Check-in at Hooch | Wall Street 

Get ready to get merry at the Santapalooza Bar Crawl 2018 in Downtown Orlando. Get exclusive drink specials and free cover at each participating venue, and come dressed as Santa or an elf, rock an ugly sweater or your Hanukkah gear for a chance to win prizes for best holiday outfit.

Ugly Sweater Party at SHOTS

When: Sat. Dec. 15th | 5 PM
Where:  SHOTS Orlando

You're invited to an old-fashioned ugly sweater holiday soiree at SHOTS Orlando. Don your hideous Christmas sweater and solidify your spot on the naughty list while sipping on some festive cocktails like Old Saint Lit and Slay Bell. 


Winter Park Snow in the Park

When: Dec. 14th 6-9 PM | Dec. 15th 9A-1P
Where:  Central Park | Winter Park

Slide down real ice slides, take photos with Santa, or roast a marshmallow with a firefighter at the inaugural “Snow in the Park,” a brand new “cool” family-friendly event in Central Park West Meadow presented by The City of Winter Park.

Holiday Carriage Rides through Downtown Winter Garden

When: Dec. 15th & 22nd | 5-9:30 PM
Where: Downtown Winter Garden

Take a horse-drawn carriage ride through festive downtown Winter Garden. Rides will commence every 15 minutes from 5:00 - 9:30 PM on Saturday, December 15th and 22nd. Reservations are required. $65.

Read More: Winter Garden (Sleighs) Holiday Season With Santa Sightings, Carriage Rides, Decor, and More

3rd Annual Iced Out Competition

When: Sat. Dec. 16th | 5PM
Where: Rosen Plaza | Orlando

What's Cooler than Cool? Ice, Carved. Orlando's top chefs put their chainsaw skills to the test, battling each other - and the Florida weather - for top honors in this annual, outdoor ice carving competition. 

Image: West Orange Times

2nd Annual Sanford Jingle Jam

When: Sat. Dec. 15th | 4-10 PM
Where:  Historic Sanford Florida

Celebrate the holidays at The 2nd Annual JINGLE JAM 2018 in Historic Downtown Sanford. One of the city's largest pet and family-friendly events, it will feature live music, holiday vendors, food trucks, a magic shows, and a visit from the Big Guy! Admission is free. 


6th Annual “Violectric Holiday Show” at Lake Eola Park

When: Fri. Dec. 14th | 7-10 PM
Where: Walt Disney Amphitheater at Lake Eola Park

Rock into the holiday season with strings sensation violectric at the 6th Annual “Violectric Holiday Show” in Downtown Orlando.

Orlando Blues & Jazz Fest (Christmas Edition)

When: Sat. Dec. 15th | 2-7 PM
Where:  Eagle Nest Park

Enjoy a day of live blues & jazz this holiday season as Orlando's best musicians play covers of your favorite Christmas tunes. Eat from over 15 food trucks and shop for those last minute Christmas gifts from craft & merchandise vendors. 

AutoNation Cure Bowl

When: Sat. Dec. 15th | 1:30 PM
Where:  Camping World Stadium

Teams from the American Athletic Conference and the Sun Belt Conference along with a stadium full of fans will aim to make history at The AutoNation Cure Bowl, a celebration of the women affected by breast cancer.

Stay connected to what's happening in your area and check out our free events calendar for new things to do in Orlando this and every weekend by subscribing to 407area. Also check out our Christmas Guide for holiday planning ideas!