10 of the Most Festive Winter Events in Sarasota

Living in Sarasota is great fun year-round, and winter is no exception. The palm trees are glowing with holiday lights, cheer is in the air, and there are plenty of fun things to do. Whether your idea of winter fun is running a costume race or cozying up at a bar, there are tons of winter events in Sarasota to make the most of the season.


“Elf” Interactive Holiday Movie Night: Dec. 15th

Head to the Museum of Art Courtyard from 5:30 p.m. to 9:00 p.m. for a Cinematic Celebration of the movie, “Elf”! Enjoy live music by Josh Walther and the Phase5 Band, holiday lights, and other fun activities, culminating with a screening of the holiday favorite. Hot chocolate, “the world’s best cup of coffee,” and candy canes are included with your ticket. Popcorn, candy, and beverages will be available for purchase, including a yuletide cocktail. Holiday attire is encouraged but not required!


Gingerbread House Festival: Dec. 15th – 17th

Feast your eyes on more than 150 gingerbread houses on display at the 9th Annual Gingerbread House Festival at Westfield Sarasota Square Mall. Each house was crafted by school kids, youth groups, local businesses, and organizations, and presented by the Girl Scouts of Gulfcoast Florida. If you see a house you like, you can reserve it for purchase and take it home for the holidays. You can also enter your own gingerbread house.


Frosty 5K Race: Dec. 16th

Get your blood pumping with the Frosty 5K Race, featuring a single-loop course followed by a festive post-race party. Participants receive a custom Frosty finisher’s medal, drawings for door prizes, and custom Frosty 5K awards. Wear a creative Frosty the Snowman costume and you might win a prize in the costume contest!


Community Chanukah Festival Israel Style: Dec. 17th

Enjoy three hours of fun, kosher food, and live entertainment at the Community Chanukah Festival at Phillippi Estate Park. Slide down the Hermon Mountain from a large four-ton snow slide, ride the Tel Aviv-Jerusalem Train, and watch BMX trick stars show off their chops. Food will be available for purchase from the area’s finest kosher caterers, including Michael’s On East.


Jingle 5K Run/Walk: Dec. 22nd

Move your feet to a jingling beat at the 6th Annual Jingle 5k Run/Walk! Join hundreds of runners and walkers for a fun run for a great cause. Every participant will receive jingle bells to tie to their shoelaces, and holiday music will follow you along the entire course. The first 1,800 runners will receive a colorful Leslie Jordan micro-mesh wicking shirt. Overall winners will receive New Balance running shoes courtesy of Fit2Run. At the finish line, a festive party awaits, with live music, food, and adult beverages. The race benefits the Lakewood Ranch Medical Center Auxiliary, which supports local community organizations and provides scholarships to those wanting a career in healthcare.


“Lights In Bloom” at Selby Gardens: Dec. 26th – 30th

Selby Gardens “Lights in Bloom” Celebration, Sarasota FL


Looking for one of the brightest winter events in Sarasota? The holiday season shines bright as more than a million lights twinkle during the Selby Gardens 14th annual “Lights in Bloom” celebration. Explore life-size garden-themed holiday lights that transform the gardens into a tropical wonderland. Enjoy games and activities as well as live entertainment with SoulRCoaster each evening. Grilled foods will be available for purchase from Michael’s on East, including a cash bar.


New Year’s Eve Pineapple Drop: Dec. 31st

It’s the annual Pineapple Drop! Celebrate New Year’s Eve all day long in Downtown Sarasota. Main Street opens at 6 p.m., and live music begins at 9:00 p.m. Grab a refreshing beverage at one of the beer stations on the Downtown streets and avenues and take advantage of special deals at local restaurants. At midnight, watch the Pineapple Drop at the intersection of Main Street and Lemon Avenue.


“Sarasota’s Best New Year’s Eve Party:” Dec. 31st

Dance your way into 2018 at the hottest New Year’s Eve Dance Party in the heart of Sarasota at The Municipal Auditorium! Reserve your tickets to this “ALL VIP” event to party with live music by Reverend Barry and the Funk, delicious gourmet food, an open bar, bottomless champagne, a laser and light show, midnight celebration, and more.


New Year’s Eve Fireworks on the Bay: Dec. 31st

Watch Sarasota’s night sky light up at the 7th Annual Fireworks on the Bay hosted by Marina Jack. The dramatic fireworks show begins at midnight, accompanied by live music. Special dinner and entertainment packages are available for purchase throughout the day and evening. Viewing is free from anywhere Downtown, including Bayfront Park and Island Park. This event benefits the Suncoast Charities for Children.


Ringling Bridge Run: Jan. 13th

Leave those winter blues in the dust and hit the road for a four-mile road race at the 15th Annual Ringling Bridge Run at 7:30 a.m. This is one of the most popular yearly Sarasota events – the run draws thousands each year. The inspiring trek is fun for runners, joggers, and walkers of all ages and abilities. There’s also a one-mile fun run that starts at 8:30 a.m. All proceeds benefit the Sarasota YMCA’s programs supporting youth and families at the Frank G. Berlin, Sr. Branch.


Have a wonderful winter in Sarasota, however, you choose to spend it! Planning to visit any of the spectacular winter events in Sarasota? We’d love to hear all about them! If you’re in the market for a new home, we hope you’ll drop by for a tour of our brand new luxury apartment homes in Downtown Sarasota. You can also take a virtual tour of our community online. Give us a call at (941) 328-2400 to schedule a tour!


Hope to see you soon!



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