# Contests Events | List Of All Upcoming Contests Events In Key West - **Subtitle**: Explore all upcoming contests events in Key West, find information & tickets for upcoming contests events happening in Key West. - **Category**: ## Featured Events - **Event Name**: The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 - **Description**: Costumes in daylight. Key West's Halloween day party crawl, 1 PM to 8 PM: 4+ bars, one wristband, no cover, then Halloween night. 21+About this Eventhttps://vimeo.com/1219059959🎃🕸️ KEY WEST HALLOWEEN D - **Date**: Sat, 31 Oct at 01:00 pm – Sat, 31 Oct at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/key-west/the-fright-crawl-key-west-halloween-day-bar-crawl-2026-sat-oct-31/100001998617717394 - **Venue**: TBA - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8zYTUwOGZkN2M2NTJkOGVjMzEwMmNlY2FjMTk2NmIwYmYyNmY4NTRkYjhkOTMzZDdlOTI2N2VlYzFlYTVjMGJjLXJpbWctdzEyMDAtaDYwMC1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODc4MzkyNjc.avif - **Price**: min: 8.17, max: 71.09, currency: USD - **Categories**: fitness, Parties, Contests, Entertainment - **Event Name**: The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 - **Description**: Halloween night in Key West, done properly. One wristband, 4+ bars, no cover, a host and a live map. Sells out first. Sat, Oct 31. 21+About this Eventhttps://vimeo.com/1219059959🎃🕸️ KEY WEST HALLOWEEN - **Date**: Sat, 31 Oct at 07:30 pm – Sun, 01 Nov at 02:00 am (-04:00) - **Event URL**: https://allevents.in/key-west/the-fright-crawl-key-wests-1-halloween-bar-crawl-2026-sat-oct-31/100001998617718397 - **Venue**: TBA - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy8wZDliYzlkNzUwZjQ1YWFiZDZiNWNkMDYyYzAwYWYwNDEwMWI3ZWE5MTY5NjMwNWUzZGNmYTNlYjgwYjA1YjcwLXJpbWctdzEyMDAtaDYwMC1kYzA4MDgxOC1nbWlyLmpwZz92PTE3ODc4MzkzMjQ.avif - **Price**: min: 8.17, max: 81.75, currency: USD - **Categories**: fitness, Parties, Contests, Entertainment ## About Explore all upcoming contests events in Key West, find information & tickets for upcoming contests events happening in Key West. ## Events in Key West - **Event Name**: 33rd Annual Homemade Bikini Contest - **Description**: Get ready to show off your DIY swimwear skills and have a blast at the 33rd Homemade Bikini showdown!About this EventRancho Relaxo Productions and the Greeen House are proud to present the 33rd Anniversary - **Interested Audience**: - Count: 1 - **Date**: Wed Oct 21 2026 at 05:00 pm – Wed Oct 21 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/key-west/33rd-annual-homemade-bikini-contest/100001999034530092 - **Venue**: Irish Kevin's - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvYTcyMWFjODhiZWJkYzM1YzA1ZTY5OGNiMDEzZmFhZmFkOTk2NDRiYzdiNmFkOTVjMTY0YTVmYWI5MDY1N2Y2My1yaW1nLXc5MDAtaDE1MDAtZGMwODA4MDgtZ21pci5qcGc_dj0xNzg3OTQ4MjU1.avif - **Price**: USD 23 to 1,069 - **Categories**: contests, festivals ## Trending Events in Key West - **Event Name**: Deep Eddy Vodka 2026 Fantasy Fest Parade - **Description**: Join 70,000 exuberant partygoers as this year’s Key West Fantasy Fest parade rolls down Duval Street. Featuring glittering floats, spectacular costumes and dazzling dancing groups! It doesn’t get any wilder than this! Parade steps off at 7 PM; FREE. Plus - **Venue**: Duval St, Key West, FL 33040, United States - **Banner**: https://cdn-az.allevents.in/events9/banners/e097be6a5846e949e56e5bf53e24c491e60feef67257b83832b6d56916e4c466-rimg-w1200-h452-dcf8f8f8-gmir?v=1788510772 - **Event Name**: Key West Fantasy Fest 2026 - **Description**: 🎆Dates: 16th - 25th October 2026 . Key West Fantasy Fest 2026 promises to live up to its claim being one of the best vibrant celebration of creativity and fun, unlike any other. This festival, - **Venue**: Key West, Florida - **Banner**: https://cdn-az.allevents.in/events9/banners/120c3c9142093a6c50a8ff24b74f0a54a6a50b39942364fb6f918ff185313c41-rimg-w1024-h576-dc284848-gmir?v=1788260151 - **Event Name**: IF THE SHOE FITS 2nd-Annual NATIONAL FINALS Live in Key West! - **Description**: Six National Finalists representing Dallas, NYC, Minneapolis, L.A., N Florida, and S Florida all vie to become the NEW "Queen of NYE"!About this EventFeaturing reigning QUEEN of New Year's Eve MULAN ALEXAN - **Venue**: Bourbon Street Pub - **Banner**: https://cdn-az.allevents.in/events5/banners/b4fb7e0362ac9fe1df66929ac5090db911177243e3b51bf1e3b50a1e5f87a03f-rimg-w1200-h1555-dc885828-gmir.jpg?v=1790794870 - **Event Name**: Captain Morgan's Masquerade March - **Description**: Join the hugely popular Fantasy Fest tradition, known as The Locals’ Parade, highlighting costumes, creativity and community. Kick off the fun at 4PM with the Paparazzi Row Block Party at Fleming & White St— strike a pose on the red carpet, hit the 36 - **Venue**: 1117 Fleming St, Key West, FL 33040-6909, United States - **Banner**: https://cdn-az.allevents.in/events1/banners/28ecde4b346e1cb5e20a7cce72d20f30afaca8a0137400682c4f66751f5fcbc8-rimg-w1200-h452-dc482868-gmir?v=1787504604 - **Event Name**: The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 - **Description**: Costumes in daylight. Key West's Halloween day party crawl, 1 PM to 8 PM: 4+ bars, one wristband, no cover, then Halloween night. 21+About this Eventhttps://vimeo.com/1219059959🎃🕸️ KEY WEST HALLOWEEN D - **Venue**: TBA - **Banner**: https://cdn-az.allevents.in/events2/banners/3a508fd7c652d8ec3102cecac1966b0bf26f854db8d933d7e9267eec1ea5c0bc-rimg-w1200-h600-dc080808-gmir.jpg?v=1787839267 - **Event Name**: LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West - **Description**: Fantasy Fest’s ultimate immersive UV blacklight GLOW party returns for its 14th glowing year!! The Theme is “LIQUID FREQUENCY”About this Event14th ANNUAL LUV2GLOW - LIQUID FREQUENCY - **Venue**: Rick's Bar - **Banner**: https://cdn-az.allevents.in/events10/banners/efab2f97b7df5f10797dfab999636805ce26e14c2194c84596a10ebb8991c85c-rimg-w1200-h600-dc1a1130-gmir.jpg?v=1783781526 - **Event Name**: Fantasy Fest Street Fair & Costume Promenade - **Description**: Duval transforms into a mile-long street party of arts, eats, and island beats. Shop whimsical crafts, feast on Caribbean flavors, sip tropical drinks, and strut your costume down Key West’s most magical mile. Friday brings arts, crafts, and food! Saturda - **Venue**: Duval St, Key West, FL 33040, United States - **Banner**: https://cdn-az.allevents.in/events4/banners/418fc3e7f0be6e9077b27a3c13060c756b27eab5dea8aea7fb923ab06ea738ce-rimg-w1200-h452-dc78d8d8-gmir?v=1787585227 - **Event Name**: The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 - **Description**: Halloween night in Key West, done properly. One wristband, 4+ bars, no cover, a host and a live map. Sells out first. Sat, Oct 31. 21+About this Eventhttps://vimeo.com/1219059959🎃🕸️ KEY WEST HALLOWEEN - **Venue**: TBA - **Banner**: https://cdn-az.allevents.in/events5/banners/0d9bc9d750f45aabd6b5cd062c00af04101b7ea91696305e3dcfa3eb80b05b70-rimg-w1200-h600-dc080818-gmir.jpg?v=1787839324 - **Event Name**: Key West OktoBREWfest - **Description**: The main tasting event takes place on Saturday, October 3rd from 3-8pm. Expect over 60 beer vendors, more than 225 types of beers, live entertainment, and a guaranteed great time! Plus the Southernmost Beach Café will be open with beer hall food specials - **Venue**: 1319 Duval Street, Key West, FL, United States, Florida 33040 - **Banner**: https://cdn-az.allevents.in/events7/banners/ce61b10fffe6d268fc896651491295c18ee1aa86e3251914634b6f0c7391e374-rimg-w1200-h628-dc0888c8-gmir?v=1787437181 ## FAQs - **Q**: What are the top events in Key West? - **A:** 33rd Annual Homemade Bikini Contest (Wed Oct 21 2026 at 05:00 pm at Irish Kevin's), The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 (Sat, 31 Oct at 01:00 pm at TBA), The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 (Sat, 31 Oct at 07:30 pm at TBA). - **Q**: What events are happening in Key West in October 2026? - **A:** 33rd Annual Homemade Bikini Contest (Wed Oct 21 2026 at 05:00 pm at Irish Kevin's), The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 (Sat, 31 Oct at 01:00 pm at TBA), The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 (Sat, 31 Oct at 07:30 pm at TBA). - **Q**: How can I find events in Key West? - **A:** You can discover upcoming events in Key West on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for events in Key West? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for events in Key West? - **A:** Some popular venues hosting events in Key West include Irish Kevin's. - **Q**: What is the price range for events in Key West? - **A:** Prices for events in Key West range from USD 8 to USD 1,069. Many events also offer free entry. - **Q**: Who are the top organizers for events in Key West? - **A:** Popular organizers hosting events in Key West include Rancho Relaxo Productions, Fright Crawl. - **Q**: Are there any online events available? - **A:** Yes, many events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new events in Key West? - **A:** Follow the category on AllEvents.in to get notified when new events are listed in Key West. ## Explore Events in Nearby Cities - [Events in Marathon](https://allevents.in/marathon-fl)