Skip to main content


24 north stamp

Best Events of Fantasy Fest 2021

Posted on: September 30th , 2021 | Events & Festivals
Best Events of Fantasy Fest 2021

2021 Fantasy Fest runs Oct. 22-31, and there’s so much planned for this year’s “All a Days for a Holiday” that it’s hard to keep tabs on the must-see attractions. Although the annual festival will look a little different this year, there are plenty of standout events we have our eye on. Also, check out the official schedule to see all there is to enjoy this year at FF.

Although we strive to provide the most current information, events mentioned may be canceled without notice. We recommend checking the official Fantasy Fest website for updates before visiting.

Monday, Oct. 25 - Heroes and Villains Run/Walk 5K

Dress as your favorite superhero or supervillain (or just come to see the costumes) at the annual Heroes and Villains Run/Walk 5K. The race winds through Old Town and there’s free beer and snacks after the relay. Register in advance and be sure to join your fellow caped contenders at Sloppy Joe’s for the afterparty. For a more scandalous spectacle, check out Fantasy Fest’s Naughty Bike Ride, which is set to proceed down Duval on the 28th.

Tuesday, Oct. 26 - Capt. Tony’s Party in Plaid

Dress in your favorite criss-crossing lines for Capt. Tony’s annual Party in Plaid. The party will have live music, cold drinks, and plenty of people bedecked in their best plaid outfit. If red is more your color (or white, or pink, or glitter) there are a few more themed circuit parties happening during Fantasy Fest - Fogarty’s Red Party (Oct. 27), Durty Harry’s 6th Annual White Party (Oct 28), Fat Tuesday’s Pink Party (Oct. 28), and Sidebar’s Glitter and Glow Party (Oct. 29).

Wednesday, Oct. 27 - Wharfstock

Travel back to the 60s with Schooner Wharf to Wharfstock. It’s all things tie-dye, flower power, peace, and love at the groovy gathering. Dress in your best hippie outfit for a chance to win prizes. If 80s jams are more your tune, read on for Irish Kevin’s annual 80s party.

Thursday, Oct. 28 - Sloppy Joe’s 42nd Annual Toga Party

The original Fantasy Fest themed event will have live music, dancing, and a house DJ. Don a traditional ancient toga or create your own using the Fantasy Fest theme “All A Daze for a Holiday.”

Thursday, Oct 28 - Fantasy Fest Scavenger Hunt/Bar Crawl

Gather your scavenger hunt team and visit Key West’s most popular watering holes. You’ll follow creative clues, solve riddles, and get tons of two-for-one drink coupons. Get your tickets ahead of time. May the best team win.

Thursday, Oct. 28 - Irish Kevin’s Annual 80’s Party

The annual party features 80s jams, 80s garb, and live entertainment. Dress in your best 80s costume (think spandex, leg warmers, shoulder pads, and big hair) for a chance to win prizes throughout the day. Listen to more legendary rock anthems at That Arena Rock Show (Oct 23), a free concert at the Sunset Pier with acts covering bands like Bon Jovi and Guns N’ Roses.


Now all you have to do is put this information to use with a trip to Key West, where summer never ends. 24 North Hotel in New Town has a low-key vibe and offers hourly shuttle service to Mallory Square. An onsite Starbucks, awesome pool area, and other amenities makes 24 North Hotel your best choice for Fantasy Fest. Check out our special offers here.

Share your opinion on this article

Special Offers
offer display image

[[offer.short_description | limitTo: 90]][[offer.short_description.length > 90 ? '...' : '']]

View Special
24 North Hotel