November 2026 Key West Events: Your Complete Guide to What's Happening in the Florida Keys
The snowbirds are starting to trickling back. And the calendars start to fill up with family gatherings and holiday events.
If you're planning a trip down the Overseas Highway, here is everything happening in Key West and the Florida Keys this November.
Race World Offshore World Championship
(November 1-8)
The month opens big. The Race World Offshore World Championship returns to Key West for a full week of high-speed offshore powerboat racing. The action kicks off on Sunday, November 1 with the World's Fastest Boat Parade rolling down Duval Street on trailers, free and open to everyone.
Race days are Wednesday the 4th, Friday the 6th, and Sunday the 8th, with boats launching from a harbor course you can watch right from shore at Truman Waterfront. The dry pits are open free all week. If you have never seen these boats up close, it is worth the trip. They are louder, faster, and more impressive than anything on TV. The races draw teams from around the world, and the whole waterfront turns into a week-long festival with food vendors, live music, and some serious people-watching.
Live Music at Key West Theater
The Key West Theater on Eaton Street continues to bring top-tier live performances to the island. November's lineup includes a mix of country, comedy, classic rock tribute, and Grateful Dead-inspired jams. Here is what is on the calendar:
November 7: Marty Stuart and His Fabulous Superlatives. Country music royalty. Marty Stuart has been making records and playing stages for over 50 years, and his live show is a masterclass in American roots music.
November 8: Dusty Slay. One of the sharpest stand-up comics working today. You might know him from late-night TV or his Netflix special. If you need a good laugh on a Saturday night, this is your show.
November 14: The Garcia Project. A night of Jerry Garcia Band and Grateful Dead music, played with the kind of love and precision that brings Deadheads out in force. Expect a long, loose, joyful set.
November 15: Chris Shutters (Pink Floyd Tribute). A full tribute to the music of Pink Floyd, complete with lights and visuals. If "Comfortably Numb" gives you chills, you want to be here.
November 22: JJ Grey and Mofro. Southern soul, funk, and rock from one of Florida's own. JJ Grey always delivers an electric live performance. Perfect way to kick off the holiday weekend.
Grab your tickets early. The Key West Theater is intimate, and shows sell out fast.
Key West Film Festival (November 18-22)
The Key West Film Festival returns for its 15th year, turning the island into a walkable cinema village for five days. Screenings happen at five walkable island venues, and the programming spans narrative features, documentaries, shorts, and animated films from around the world.
What makes this festival special is the access. Filmmakers stick around for Q&A sessions after screenings, and you can run into directors and producers at the same bars and restaurants you already love. The festival also hosts panels, industry conversations, and evening events that blend film culture with Key West nightlife. Whether you are a serious cinephile or just looking for something different to do on a November evening, the Film Festival is one of the cultural highlights of the year.
Art Walks and Gallery Nights
Key West's art scene comes alive in November with two signature gallery events.
First Thursday Art Walk (November 5): Galleries along Duval Street and throughout Old Town open their doors from 5 to 9 PM with new exhibitions, refreshments, and live artist demonstrations. It is one of the best free things to do in Key West, and a great way to discover local and visiting artists. More details at keywestartandhistorical.org.
Last Friday Gallery Walk (November 27): The Studios of Key West and other galleries host a walkable evening of art viewing on the last Friday of the month. Think of it as a more neighborhood-level version of the First Thursday event, with a relaxed post-Thanksgiving vibe. Details at tskw.org.
Fishing and Outdoor Fun
November is prime season for fishing in the Florida Keys. Water temperatures are comfortable, the crowds thin out after Fantasy Fest, and the fish are biting.
The Sugarloaf Showdown, November 12 through 14, is a catch-and-release flats tournament out of Sugarloaf Key, about 20 minutes north of Key West. It is a great chance to watch serious anglers compete for tarpon, permit, and bonefish on the flats. Even if you are not fishing, the weigh-in events and dock parties are worth a visit.
Thanksgiving Week in Key West
Thanksgiving in Key West is a different kind of holiday. You can have your turkey dinner with the windows open and a warm breeze coming in off the water.
November 26 (Thanksgiving morning): Lace up for the Southernmost Turkey Trot 5K, starting at 8 AM. It is a flat, fast, scenic run through Old Town, and you will earn that second helping of pie.
November 27 (Friday evening): Head to the Key West Harbor Walk of Lights for the annual holiday lighting ceremony. The harbor boardwalk lights up for the season, and it is a beautiful way to ease into the holiday spirit.
Many of Key West's best restaurants offer special Thanksgiving menus, so if you would rather let someone else do the cooking, you will have plenty of options. The long weekend is also a popular time for visitors, so book early if you are planning a trip.
Veterans Day (November 11)
Key West has a deep connection to the military, with Naval Air Station Key West right here on the island. Veterans Day is observed with a parade down Duval Street and a ceremony at the Bayview Park Veterans Memorial. It is a meaningful day in a town that has always had strong ties to the service. Local businesses often run specials for veterans and active-duty military.
Key West Artisan Market
Every Sunday morning from 10 AM to 2 PM, the Key West Artisan Market pops up at Higgs Beach. Local vendors sell handmade goods, art, jewelry, baked treats, and more. It is a casual, family-friendly way to spend a Sunday morning, and a good spot to pick up unique gifts as the holidays approach. Grab a coffee, stroll the booths, and enjoy the ocean breeze. The market runs every Sunday in November: the 1st, 8th, 15th, 22nd, and 29th.
Every Week in Key West
Beyond the big events, Key West has a rhythm of weekly happenings that make everyday life here feel full.
Sunset Celebration at Mallory Square: Every evening, rain or shine. Street performers, local artists, food carts, and one of the most photographed sunsets in the world. It is free and never gets old. Learn more at sunsetcelebration.org.
Live Music on Duval Street: Nightly. From Sloppy Joe's to the Hog's Breath Saloon to the Green Parrot, live music pours out of nearly every door. No cover, no reservations, just walk in and enjoy.
Fort Zachary Taylor State Park: Open daily. One of the best beaches in Key West, with great snorkeling right off shore. Pack a cooler, grab a spot under the trees, and spend the afternoon. Details at floridastateparks.org.
Key West Butterfly and Nature Conservatory: Open daily. A lush, glass-enclosed habitat with over 50 species of butterflies, flowering plants, and birds. A great option for families or anyone who wants a quiet, beautiful escape. More at keywestbutterfly.com.
Thinking About Living Here?
If this list has you daydreaming about calling Key West home, you are not the first. November is when a lot of people fall in love with the island, and it is easy to see why.
If you are thinking about buying a home here, investing in a rental property, or just exploring what life in the Florida Keys looks like, I would love to help. I have been here since 2003 and know this island inside and out. Reach out anytime.
Frequently Asked Questions About Key West in November
What are the biggest events in Key West in November 2026?
The two marquee events are the Race World Offshore World Championship (November 1-8), featuring high-speed offshore powerboat racing along the Key West harbor, and the Key West Film Festival (November 18-22), a five-day celebration of independent cinema with screenings at five walkable island venues.
Is there a Thanksgiving event in Key West?
Yes. The Southernmost Turkey Trot 5K starts at 8 AM on Thanksgiving morning, November 26, with a flat scenic run through Old Town. On Friday evening, November 27, the Key West Harbor Walk of Lights ceremony kicks off the holiday season with a beautiful boardwalk lighting along the harbor.
Where can I see live music in Key West in November?
The Key West Theater on Eaton Street has ticketed shows throughout November, including Marty Stuart (Nov 7), Dusty Slay (Nov 8), The Garcia Project (Nov 14), a Pink Floyd tribute (Nov 15), and JJ Grey and Mofro (Nov 22). For free live music, Duval Street bars like Sloppy Joe's, Hog's Breath Saloon, and the Green Parrot have nightly performances.
Are there free things to do in Key West in November?
Yes, plenty. The Sunset Celebration at Mallory Square happens every evening and is free. The First Thursday Art Walk (November 5) and Last Friday Gallery Walk (November 27) are free gallery events. The Veterans Day parade on November 11 is open to the public. The Key West Artisan Market at Higgs Beach is free every Sunday morning.
All The Best From The Florida Keys.
Krystal Sheehan | eXp Realty | Licensed in Florida
Comments