# Challenge Events | List Of All Upcoming Challenge Events In Key West - **Subtitle**: Explore all upcoming challenge events in Key West, find information & tickets for upcoming challenge events happening in Key West. - **Category**: ## About Explore all upcoming challenge events in Key West, find information & tickets for upcoming challenge events happening in Key West. ## Events in Key West - **Event Name**: The Fright Crawl | Key West Halloween Bar Crawl 2026 | Fri, Oct 30 - **Description**: Key West's hottest Halloween bar crawl on Friday, October 30th. Featuring the city's best bars & clubs, live DJs, and no cover! - **Date**: Fri Oct 30 2026 at 07:30 pm – Sat Oct 31 2026 at 02:00 am (-04:00) - **Event URL**: https://allevents.in/key-west/the-fright-crawl-key-west-halloween-bar-crawl-2026-fri-oct-30/100001998617713382 - **Venue**: TBA - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvZWJjZjk2MjhiY2MzYzQwYzM2ZDJiNjM5MzNkMzA2YThmYzFlNzc1NmM0YTgzMmRkMjAxZjg4MWNiN2MyNTk4OS1yaW1nLXcxMjAwLWg2MDAtZGMwODA4MDgtZ21pci5qcGc_dj0xNzg3ODM5MzMy.avif - **Price**: USD 8 to 71 - **Categories**: fitness, Parties, Entertainment, Contests - **Event Name**: The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 - **Description**: Key West's biggest Halloween day party and bar crawl. The city's best bars, music, and no cover. Sat, Oct 31 β€” 800 spots.About this Eventhttps://vimeo.com/1219059959πŸŽƒπŸ•ΈοΈ KEY WE - **Date**: Sat Oct 31 2026 at 01:00 pm – Sat Oct 31 2026 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:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8zYTUwOGZkN2M2NTJkOGVjMzEwMmNlY2FjMTk2NmIwYmYyNmY4NTRkYjhkOTMzZDdlOTI2N2VlYzFlYTVjMGJjLXJpbWctdzEyMDAtaDYwMC1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODc4MzkyNjc.avif - **Price**: USD 8 to 50 - **Categories**: parties, entertainment, bar-crawls, halloween-parties, halloween, contests, pub-crawl, costume-parties, holiday - **Event Name**: The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 - **Description**: Key West's biggest Halloween bar crawl. The city's best bars & clubs, live DJs, no cover. Sat, Oct 31 β€” 800 spots.About this Eventhttps://vimeo.com/1219059959 - **Date**: Sat Oct 31 2026 at 07:30 pm – Sun Nov 01 2026 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:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy8wZDliYzlkNzUwZjQ1YWFiZDZiNWNkMDYyYzAwYWYwNDEwMWI3ZWE5MTY5NjMwNWUzZGNmYTNlYjgwYjA1YjcwLXJpbWctdzEyMDAtaDYwMC1kYzA4MDgxOC1nbWlyLmpwZz92PTE3ODc4MzkzMjQ.avif - **Price**: USD 8 to 82 - **Categories**: parties, entertainment, bar-crawls, halloween, halloween-parties, contests, pub-crawl, costume-parties, holiday - **Event Name**: The Fright Crawl | Key West Halloween Bar Crawl 2026 | Thurs, Oct. 29 - **Description**: Key West's craziest Halloween bar crawl on Thursday, October 29th. Featuring the city's best bars & clubs, live DJs, and no cover! - **Date**: Thu Oct 29 2026 at 07:30 pm – Fri Oct 30 2026 at 02:00 am (-04:00) - **Event URL**: https://allevents.in/key-west/the-fright-crawl-key-west-halloween-bar-crawl-2026-thurs-oct-29/100001998617701346 - **Venue**: TBA - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy81MDQxMmQyMWQ5MDQ2OGRiMTA1ZjI3MGMxMDk1ZTYyNDI0ODc1MWRhNWIxMGJiNWY1OTI0ODk2NWNmM2FiOGQxLXJpbWctdzEyMDAtaDYwMC1kY2Y4ZjhmOC1nbWlyLmpwZz92PTE3ODc4MzkyNjU.avif - **Price**: USD 8 to 50 - **Categories**: fitness, Parties, Entertainment, Contests - **Event Name**: Brews & Blues - **Description**: Cold brews, live blues, and backyard fun! Join us poolside for an official Key West oktoBREWfest celebration.About this EventKick off your oktoBREWfest weekend at Brews & Blues, a liv - **Interested Audience**: - Count: 1 - **Date**: Fri Oct 02 2026 at 05:00 pm – Fri Oct 02 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/key-west/brews-and-blues/100001997848775468 - **Venue**: Blue Flamingo Resort Key West - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy84YTIwNzMyNTNhYWFhMTZiMTRiOWRmZWQzOTc0NDE2ZjQ5YWQzZDcxZDFlMzFjOTUxZTAxNzA4MjhjZWFhOWNiLXJpbWctdzEwODAtaDEzNTAtZGNmOGY4ZjgtZ21pci5qcGc_dj0xNzg2Njc2NDU3.avif - **Price**: Free - **Categories**: fitness, Music, Contests, Entertainment, Festivals, trips-adventures - **Event Name**: 29th Annual Key West Half Marathon & Runfest - **Description**: Ready-Set-RUN! The 29th Annual Key West Half Marathon & Runfest is almost upon us! Starting at the Key West Historic Seaport at the corner of Caroline Street & Grinnell Street (less than a block from the packet pickup location), thousand of runner - **Interested Audience**: - Count: 82 - **Date**: Fri Jan 15 2027 at 04:00 pm – Mon Jan 18 2027 at 07:00 pm (-05:00) - **Event URL**: https://allevents.in/key-west/29th-annual-key-west-half-marathon-and-runfest/200029613028241 - **Venue**: Key West Historic Seaport - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy81NzI0ZDZmN2VhMWVmODQzMjkzNjZlMWViZGMyYzZlYWIyZTQzNmEyMzU3ZTNjZDYwNjFjODkwNWUzZDg2NGM1LXJpbWctdzEyMDAtaDY3NS1kYzA4ODg4OC1nbWlyP3Y9MTc4Njc2NTIxMQ.avif - **Categories**: marathons, sports, contests ## Trending Events in Key West - **Event Name**: Duval Street Party with the Landshark Band - **Description**: 🎢🌴 Duval Street Concert: Meeting of the Minds Throwback featuring Gary & the Landsharks πŸ“… Friday Β· September 4 Β· 6:00–9:30 PM πŸ“ Duval Street, Key West Hosted by Sloppy Joe’, Irish Kevin’s & Rick's Place Step into a piece of Parrot Head history a - **Venue**: 200 Duval St, Key West, FL 33040, United States - **Banner**: https://cdn-az.allevents.in/events6/banners/b61001d22c3d02d75370772baab08b776980dbc0ca88e7567c4d63c86818d026-rimg-w1200-h629-dc080808-gmir?v=1787437165 - **Event Name**: Cheese Burger Beach Battle and Tribute Concert - **Description**: Cheeseburger Beach Battle and Tribute Concert πŸ“… Thursday, September 3 Β· 5:00–8:00 PM πŸ“ Southernmost on the Beach Β· 508 South St, Key West πŸ•’ Event Timeline β€” 4:30 PM β€” Gates open Β· bars & food available β€” 5:00–7:00 PM β€” Burger tasting & voting β€” - **Venue**: Southernmost Beach Resort - **Banner**: https://cdn-az.allevents.in/events5/banners/9363b7502f4abe1932898847e6945468f0d8f3768296fa4182d7f66e8c3b365c-rimg-w1200-h629-dcf8f8f8-gmir?v=1787663593 - **Event Name**: Taste of Key West 2027! - **Description**: The 32nd Annual Taste of Key West! Celebrate 32 years of flavors at the Taste of Key West! Enjoy an unforgettable evening of delicious bites, fine wines, and craft beers, all with stunning waterfront views. 🍽️ Tastings from 40+ incredible local restau - **Venue**: Truman Waterfront, Key West, FL, United States, Florida 33040 - **Banner**: https://cdn-az.allevents.in/events10/banners/a3480ae30ebf762c97e7742854683d40cdae6e0ff7db4e7905deda0b700d5388-rimg-w1200-h675-dcf8f8e8-gmir?v=1787702133 - **Event Name**: Will Kimbrough - Live in the Chart Room - **Description**: Will Kimbrough: Live in the Chart Room πŸ“… Monday, September 7, 2026 Β· 10:00 AM – Noon πŸ“ Pier House Resort & Chart Room Bar, Key West 🎟️ Limited to just 38 guests Β· $250 per person This may become one of the most unforgettable moments of the entire we - **Venue**: Pier House Resort & Spa - **Banner**: https://cdn-az.allevents.in/events5/banners/45f2f62bb1090d971b0b08a2f1df275a66394406a6d5d0a4c407672ee8a823d3-rimg-w1200-h629-dc080808-gmir?v=1787206382 - **Event Name**: Second Line Memorial Walking Parade - **Description**: Second Line Memorial Procession: A Tribute to Key West’s Favorite Son πŸ“… Sunday Β· September 6 Β· 5:00 PM πŸ“ Lower 100 Block of Duval Street to Truman Waterfront Park, Key West Celebrate the life, music, and spirit of Key West’s favorite son with a joyful, t - **Venue**: 100 Duval St, Key West, FL 33040-6506, United States - **Banner**: https://cdn-az.allevents.in/events4/banners/4dc548ff3c5cba8cc754bcaae148305965a050b3e44b20e0031ca2898e4bc922-rimg-w1200-h628-dc08e8e8-gmir?v=1787112960 - **Event Name**: Key West's Favorite Son City Proclamation - **Description**: πŸ“œ Key West’s Favorite Son City Proclamation πŸ“… Friday, September 4, 2026 ⏰ 11:00–11:30 AM πŸ“ Shrimp Boat Sound Studio Β· Lazy Way, Key West Join city, county, and state leaders, local personalities, and representatives of the Conch Republic at the pocket p - **Venue**: Shrimp Boat Sounds (Jimmy Buffetts Recording Studio) - **Banner**: https://cdn-az.allevents.in/events10/banners/3af05be83439649a085f323c24496ad664be035ba0a9de8d44ed7ef88f79b740-rimg-w1200-h629-dcf8f8f8-gmir?v=1787458757 - **Event Name**: Just a Few Friends Celebration, Key West - **Description**: Just a Few Friends Key West 2026 Β· Labor Day Weekend Celebration πŸ“… September 3–7, 2026 πŸ“ Key West, Florida Join us in Key West for Labor Day Weekend as the island comes alive for the 3rd Annual Just a Few Friendsβ€”a five-day, island-wide celebration honor - **Venue**: Key West - **Banner**: https://cdn-az.allevents.in/events6/banners/b528b87b0ef3df8427ba88dc368bd666967f54e6286e93d197bd3fb42e0e0def-rimg-w1200-h629-dc281818-gmir?v=1787122911 - **Event Name**: The Wheeland Brothers + Mike Stack & Friends at Sunset Pier - **Description**: πŸŒ… Sunset Pier Concert: Wheeland Brothers + Mike Stack & Friends πŸ“… Saturday, September 5, 2026 πŸ“ Sunset Pier Β· 0 Duval St, Key West ⏰ 6:30 PM Β· Mike Stack & Friends ⏰ 8:00 PM Β· Wheeland Brothers There’s no better place in Key West to watch the s - **Venue**: Sunset Pier, Key West, FL 33040, United States - **Banner**: https://cdn-az.allevents.in/events3/banners/bf0d56c248156c3b537b3b84ff2e0e9bccd4ed203416638514fd13ba3a5ca942-rimg-w1200-h629-dcf8f8f8-gmir?v=1787542863 - **Event Name**: Landsharks Band Jimmy Buffett Tribute in Key West - **Description**: Landsharks Band, Key West Concert, "JUST A FEW FRIENDS" CONCERT WEEKEND! Honoring Jimmy Buffett! The Landsharks will re-enact their legendary concert with Jimmy Buffett, on Duval Street, in Key West, in 1999. September 4, 2026, 5pm https://www.justafewfr - **Venue**: Duval St Key West Florida - **Banner**: https://cdn-az.allevents.in/events3/banners/2b5fcb1cb9da7c71addbcf89db20ae08c2ad02e5a240431875995a821461a829-rimg-w1200-h762-dcf85888-gmir?v=1787803504 ## FAQs - **Q**: What are the top events in Key West? - **A:** The Fright Crawl | Key West Halloween Bar Crawl 2026 | Fri, Oct 30 (Fri Oct 30 2026 at 07:30 pm at TBA), The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 (Sat Oct 31 2026 at 01:00 pm at TBA), The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 (Sat Oct 31 2026 at 07:30 pm at TBA), The Fright Crawl | Key West Halloween Bar Crawl 2026 | Thurs, Oct. 29 (Thu Oct 29 2026 at 07:30 pm at TBA), Brews & Blues (Fri Oct 02 2026 at 05:00 pm at Blue Flamingo Resort Key West). - **Q**: What are the top free events in Key West? - **A:** Brews & Blues (Fri Oct 02 2026 at 05:00 pm at Blue Flamingo Resort Key West). - **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 Blue Flamingo Resort Key West, Key West Historic Seaport. - **Q**: What is the price range for events in Key West? - **A:** Prices for events in Key West range from USD 8 to USD 82. 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 Fright Crawl, Highgate, Key West Half Marathon & 5K Run. - **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)