Miami Beach doesn’t follow the typical seasonal script. Fall and winter arrive not with cold fronts, but with a full calendar: harvest festivals, seafood feasts, outdoor film nights, and art shows that pull the world’s attention. It’s a stretch of the year built around gathering at the table, in the streets, by the sea.

At Cadillac Hotel & Beach Club, we tend to plan our season around what’s happening out there, events we mark early and recommend often. Here are a few worth making space for.

Harvest Festivals & Pumpkin Patches

September–November 2025

In South Florida, autumn brings its own take on the harvest season. The Berry Farm’s Harvest Festival fills weekends with live music, hayrides, a corn maze, and food that leans into seasonal comfort. For something more intimate, The Little Farm’s Fall Festival offers a more hands-on, close-up kind of experience, including pony rides, animal feedings, and a pumpkin patch that feels thoughtfully tucked into the landscape.

For those simply seeking the ritual of picking the perfect pumpkin, By Brothers Pumpkin Town and Pinto’s Farm Pumpkin Patch offer the works: rows of pumpkins, photo ops, and farm treats. It’s fall, reimagined in Miami hues—colorful, cultural, and impossible to sit out.

Headliners at Kaseya Center

September–November 2025

Some nights call for something louder. This season’s lineup at Kaseya Center includes Lady Gaga (September 1 & 3), Dua Lipa (September 26 & 27), Billie Eilish (October 9, 11 & 12), and Jo Koy (November 15). Whether it’s a concert or a comedy set, these are the kinds of nights that turn a stay into a story.

South Beach Seafood Festival

October 22–25, 2025

Few events capture Miami’s coastal point of view like the South Beach Seafood Festival. Local chefs, fresh catches, open-air tastings—it’s a full afternoon of food, music, and ocean breeze, all set against the backdrop of the beach. It’s laid-back in setting, focused on details, the way only Miami could pull off.

Oktoberfest Miami

October 10–19, 2025

Brimming with live music, hearty Bavarian fare, and traditional folk dancing, Oktoberfest Miami brings the charm of a German autumn to the tropics. It’s a gathering that feels both celebratory and grounded, with families clinking steins under the trees and accordion notes carrying through the air. For a taste of old-world tradition wrapped in Miami ease, this is where we like to raise a toast.

Miami Film Festival GEMS

October 29–November 5, 2025

Not everything needs a red carpet. GEMS is where smart films meet a smaller, more attentive crowd. Curated, international, and often under the radar, GEMS offers a tighter, more focused lineup than its spring counterpart, and that’s exactly the draw. Think fewer crowds, better conversations, and stories that stay with you.

Miami Book Fair

November 16–23, 2025

The Miami Book Fair turns downtown into something closer to a bookstore plaza. Panels spill out onto streets lined with books, families browse under open tents, and poets read in tucked-away courtyards. We tend to leave with too many books and not a hint of regret.

Art Basel Miami & Miami Art Week

December 5–7, 2025 | December 1–7, 2025

Each December, Art Basel and Miami Art Week transform the city into one of the art world’s busiest hubs. Installations take over hotels, storefronts, and sidewalks. Wynwood gets a fresh coat of imagination, and galleries stretch from the Design District to the beach. Whether you pace yourself or dive right in, everywhere you turn, there’s something bold, immersive, and unexpected.

Winter Light Festivals

November–January 2025

As winter settles in, if only by the calendar, Miami trades neon for twinkle lights, turning parks and plazas into something festive and fleeting. Zoo Lights Miami offers a wonderland of illuminated animals and festive installations. Over in Coral Gables, Night at the Garden at Fairchild Tropical Botanic Garden blends projection mapping with live performances beneath banyan canopies.

Closer to home, the Miami Beach Holiday Festival of Lights and Downtown Miami Holiday Village bring cheer through music, market stalls, and warm evenings dressed in twinkle lights. And at Tropical Park’s Christmas Wonderland, families glide across ice rinks, ride holiday trains, and gather around cocoa stands under a carousel of lights.

Savoring the Season, Cadillac Style 

Between the festivals and the city’s buzz, there’s comfort in knowing what’s waiting at Cadillac Hotel & Beach Club. A quiet morning espresso, an open afternoon by the pool, an evening that ends with rosé and fresh pasta. When the days are full, in the best ways, it helps to come back to something calm, familiar, and well-considered.

This season offers plenty to plan around. We’ll be here when you’re ready to make it yours.