Spend the holiday season with friends and family exploring all that Key West has to offer! Monroe County residents can enjoy the Old Town Trolley tour for FREE when accompanied by a full fare adult paid guest with Hometown Pass.
Dates: December 1, 8, 15, 22, 29. Gather your team or come solo and make new friends as we challenge your brain with a mix of pop culture, history, food facts, and island oddities. Fabulous prizes await the top scorers — and maybe even a few surprises for the most creative answers! While you play, enjoy exclusive bar specials and a mouthwatering Trivia Night menu crafted just for the occasion. It’s the perfect mix of delicious bites, cold drinks, and great vibes.
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1:00 PM - 3:00 PM
Santa at Key West Cooking Show
Key West Cooking Show, 291 Front Street, Upstairs
Santa himself will be visiting the Key West Cooking Show. The jolly old man in the red suit will be working on his list of who has been naughty or nice. Kids of all ages can have their pictures taken, post letters, and enjoy cookies and cider.
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5:00 PM - 8:00 PM
Holiday Concert and Bazaar
Key West Custom House, 281 Front Street
The Key West Art and Historical Society’s annual Holiday Concert and Bazaar is a local holiday favorite. The evening is a great time to shop, mingle, and get into the holiday spirit.
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11:00 AM - 2:00 PM
First Annual Great Gingerbread Build
Harry S. Truman Little White House, 111 Front Street
Come one, come all to the First Annual Great Gingerbread Build at the Harry S. Truman Little White House. This event is free and open to the public. We will have gingerbread crackers, icing, and all sorts of candies to decorate your house with, or we will also have a limited amount of kits available to buy if you wish to create something a little more formal. Everything will be available on the beautiful lawns of the stunning Harry S. Truman Little White House, so come with your creativity and season’s cheer to just have fun with children of all ages welcome.
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1:00 PM - 3:00 PM
Sheriff’s Animal Farm Open House
Stock Island Detention Center, 5501 College Rd.
Visit the family-friendly Monroe County Sheriff’s Animal Farm. Animals include a capybara, possum, sloths, goats, birds, and many more. Visits are free, but cash or fresh produce donations are always welcome.
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1:00 PM - 3:00 PM
Sheriff’s Animal Farm Open House
Stock Island Detention Center, 5501 College Rd.
Visit the family-friendly Monroe County Sheriff’s Animal Farm. Animals include a capybara, possum, sloths, goats, birds, and many more. Visits are free, but cash or fresh produce donations are always welcome.
