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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

Falyn Wood
Written by
Falyn Wood
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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

  • Things to do
  • Performances

The Miami Dolphins, the 2020 election and royal family drama should all be ample fodder for lampooning during the 38th annual Coconut Grove parade, which sports wild floats and locals donning their wackiest satirical costumes, as well as high school and professional marching bands.

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  • Things to do
  • Festivals

This yearly hops-head’s paradise pours at least 200 beers from dozens of South Florida and international craft breweries. Yes, there will be DJs performing on the JumboTron and food trucks. Plus, you don’t have to feel guilty about throwing a few back: Ticket proceeds will go to Hialeah’s 1 Lucky Dog Rescue.

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South Beach Wine and Food Festival
  • Things to do
  • Festivals

Celebrity chefs (more than 450 of them) and hungry Miamians take to the sands of South Beach for Miami’s biggest and most famous annual food festival, all proceeds of which benefit Florida International University’s Hospitality & Tourism Management school. Seriously, this thing is huge. There are burger battles and tasting villages and more calories than you’ll know what to do with. Plus, Guy Fieri! Wash it all down with wine, of course. Various locations

  • Things to do
  • Exhibitions
  • Miami

One of the best things to come out of Art Basel 2018 was a video of Kanye West talking to a tree. It wasn’t another psychotic break, thankfully. The rapper was spitting it back to Archimedes, the creepily captivating talking tree at NightGarden, Fairchild Tropical Botanic Garden’s psychedelic neon playground. The pop-up exhibit returns for its second year, taking over a portion of the 80-acre property and turning it into an illuminated wonderland. Think technicolor mazes, scavenger hunts led by virtual fairies, an enchanting snowfall experience, glowing dandelion fields and, yes, the infamous talking tree.

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  • Things to do
  • Festivals

IPA and fruited-sour enthusiasts will get satiated at this celebration of beer, with selections from Jupiter’s Civil Society Brewing Co., New York’s Finback Brewery, Richmond’s Ardent Craft Ales and many others. Tickets include unlimited tastings and a custom festival glass. If you need to quell your buzz, the pop-up burger joint USBS will be ready to take your order.

  • Things to do
  • Festivals

The explosive queer festival anchored at Gramps in Wynwood returns for a fourth year. Judging from 2019’s bonkers three-day marathon of “Under the Sea”–themed parties that showcased all-stars from the Magic City’s drag scene and other LGBTQ circles, the 2020 fest is bound to be a wild ride. Locations and times TBA

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  • Things to do
  • Festivals

Ten stages with a variety of live performances, drunken revelers reppin’ their country’s flag and all the croquetas and arepas you can stuff into your face. It’s time for Miami’s massive street fair, Calle Ocho, where thousands of people gather across the iconic 20 blocks every year to celebrate Latin pride. It is truly a celebration of everything that makes Miami special. Don’t miss it. SW 8th St between SW 12th and 27th.

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  • Things to do
  • Sport events

The million dollar horse race ($9 million, to be exact) comes to Gulfstream Park. Not into horses? Come for the atmosphere, which, if similar to year’s past, will likely border on South Beach nightclub thanks to a day party hosted by LIV’s David Grutman plus food and beverage offerings from his luxe eateries Komodo, Swan, Bar Bevy and Papi Steak. Details on 2020’s entertainment to come. 

Looking for more awesome things to do around town?

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