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Pegasus World Cup Invitational
Photograph: Courtesy Pegasus World Cup

The best events happening this winter in Miami to add to your calendar now

Winter in Miami means glorious weather, huge festivals and one seriously packed schedule

By Falyn Freyman

Winter in Miami sure is something. While the rest of the country shivers, we slowly crawl out of the air-conditioned dens where we hid most of the year and begin to reclaim our city. Honestly, we feel for you, America. You have to hide under a blanket while we’re spreading one at the best Miami beaches. You have to survive on hot soup and tea while we get to throw back some rosé at the best waterfront bars in Miami. Plus, the biggest festivals, concerts and parties of the year all happen in a short three-month span. We hope you got some rest during that lazy summer. Because you’re going to need every ounce of energy this winter.

RECOMMENDED: The best things to do in Miami right now

Winter events in Miami

Fillmore Miami Beach at the Jackie Gleason Theater for the Performing Arts, Music and nightlife, Miami
Photograph: Jason Koerner

17. Rex Orange County

Things to do Concerts

While his work with Benny Sings and Tyler, the Creator made his name, Alexander O’Connor’s two 2019 singles, “New House” and “10/10,” and his upcoming album Pony are sure to spread his brand of sunny, romantic indie pop everywhere.

Pyramid People Art Basel
Photograph: Courtesy Unsplash/Denys Nevozhai

18. Love Burn 2020

Things to do Festivals

South Florida’s official homage to Burning Man transforms that event’s principles of radical self-expression and community into a beachfront camping experience. Expect fantastical themes, musical performances and art exhibits that focus on this year’s “Femme Futuro: The Matriarchy Reloaded” theme.

Miami Beach Gay Pride 2016
Photograph: Patrick Farrell

19. Gay8 Festival

Things to do Festivals

For the fifth year in a row, Gay8 takes to the streets of Little Havana for a one-day festival celebrating Miami’s Latino LGBTQ culture—and what a remarkably vibrant culture it is. Expect food, art, music and more proudly marching down Calle Ocho in a glorious rainbow of colors. 2436 SW 8th St.

Fillmore Miami Beach
Photograph: Courtesy GMCV

20. Leoni Torres

Things to do Concerts

One of the biggest stars in contemporary Cuban music, Leoni Torres clearly knows his audience: He’s slated to play two Miami shows—one on Valentine’s Day—as part of his Amor Bonito tour. After spending time with David Calzado in the celebrated group La Charanga Habanera, he went solo to unleash his modern take on Cuban pop, as heard in songs like “Me Quedo Contigo.”

Art Deco Miami
Photograph: Shutterstock

21. Art Deco Weekend

Things to do Festivals

Relive all things Jazz Age at the Miami Design Preservation League’s annual festival, with live music, an Art Deco–inspired fashion show, a dog-costume competition, antique cars, food and craft vendors, and walking tours that gloss Miami Beach’s unique architecture. Celebrating women’s suffrage, this year’s theme is “Sheroes: Women Who Made a Difference.” Fifth to 15th Sts and Ocean Dr, Miami Beach at various times

North Beach Bandshell
Photograph: Courtesy North Beach Bandshell

22. GroundUp Music Festival

Things to do Concerts

Hosted and headlined by the jazz-funk collective Snarky Puppy, this three-day beach fest gives attendees an intimate experience via workshops with artists and hangouts with musicians. The lineup includes Michael McDonald, Miami-raised jazz vocalist Cécile McLorin Salvant and Flor de Toloache, an all-women mariachi group.

ING Miami Marathon
Photograph: Courtesy ING Miami Marathon

23. Miami Marathon and Half Marathon

Things to do Sport events

Lace up for Miami’s most popular racing event. Now in its 18th year, the run winds through the city’s most scenic neighborhoods, from Bayfront Park to Coconut Grove and Key Biscayne. Your cardio not quite up to marathon levels? You can still partake! Supporters are encouraged to cheer along the way. 

Photograph: Unsplash/Charisse Kenion

24. International Chocolate Weekend

Things to do Festivals

Fairchild Tropical Botanic Garden dedicates two full days to the beloved cocoa bean for this 14th-annual event. The main star of the show—if you couldn’t guess—is chocolate. Don’t miss your opportunity to taste samples from artisan chocolatiers, sit in on lectures and participate in all sorts of sweet demonstrations.

Photograph: Unsplash/Ruthie

25. Miami International Map Fair

Things to do Markets and fairs

Between Waze and Google, do you remember the last time you used a paper map? What a shame! Maps are cool. You can’t throw darts at an iPhone. At the Miami Map Fair, one can recall the simple pleasures of thumbing through an atlas, spinning a globe and seeing colorful antique versions at the largest map fair (take that, other map fairs!) in the country.

Looking for more awesome things to do around town?


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