Halloween Week in Key West 2025
October 28, 2025 • Key West Tourist
🎃 Halloween Week in Key West 2025: Family Fun, Haunted Nights & Sunday Market Magic
Free Family Halloween Party at Truman Waterfront Park
Date: Thursday, October 30, 2025 • Time: 4:00 p.m.–7:00 p.m.
Location: Truman Waterfront Park, end of Southard Street
Presented by: Key West Chamber of Commerce & Keys Artisan Market
The Free Family Halloween Party at Truman Waterfront Park kicks off Halloween week with a fun-filled evening designed especially for families. Children can enjoy trick-or-treating among vendor tents, explore the Haunted Bus courtesy of City of Key West Transit, and bounce through inflatable play zones from Four Star Rentals. Local partners such as H&R Block keep spirits high with sweet giveaways, while live music adds to the festive waterfront atmosphere.
Why Visit: This community celebration offers a safe, lively Halloween experience by the sea with unforgettable sunset views.
Pro Tip: Bring lawn chairs or a blanket to enjoy the sunset along the seawall before the city nightlife begins.
Duval Street Halloween Parties & Haunted Tours
Date: Friday, October 31, 2025
When night falls, Key West’s Duval Street transforms into a lively scene of costume parties, live music, and spooky adventure. Popular hotspots like Schooner Wharf Bar and The Salty Frog host themed Halloween bashes with contests, golden-hour drink specials, and island beats that roll into the early hours.
Those seeking a chill down the spine can book haunted walking tours and trolley rides that dive deep into Key West’s haunted history. The Dark Side of Key West Walking Tour offers eerie tales for adults, while the Ghosts & Gravestones Guided Trolley Tour delivers a haunting journey through centuries of mystery and lore.
Why Visit: A Halloween celebration like no other — full of costumes, cocktails, and captivating ghost stories.
Pro Tip: Start your night with a cocktail at the waterfront and catch the sunset before diving into the downtown festivities.
Keys Artisan Market at Higgs Beach
Date: Sunday, November 2, 2025 • Time: 10:00 a.m.–2:00 p.m.
Location: Higgs Beach, parking lot of Indigenous Park, 1801 White Street
Presented by: Keys Artisan Market
After a weekend of revelry, unwind at the Keys Artisan Market at Higgs Beach. Visitors can browse handmade goods, enjoy local food trucks, and relax to live island music in a breezy beachfront setting. Artisans showcase everything from handcrafted jewelry and tropical wood art to organic produce and creative gifts.
Why Visit: This open-air event blends beachside charm with authentic local culture — a perfect Sunday unwind for visitors and locals alike.
Pro Tip: Arrive early for the best selections, then brunch at a nearby White Street café.
Weekly Key West Farmers Market
Date: Every Thursday • Time: 2:00 p.m.–7:00 p.m.
Location: Truman Waterfront Park
The Key West Farmers Market continues each Thursday, bringing together fresh produce, artisan meats, cheeses, and handmade goods under the afternoon sun. The market’s scenic setting at Truman Waterfront Park offers an ideal stop for fresh bites, local gifts, and sunset shopping.
Why Visit: The island’s favorite spot for local treats and laid-back browsing with unbeatable harbor views.
Pro Tip: Arrive early before the Halloween Family Party to enjoy local flavors and shop before festivities begin.
