Key West Tropical Forest and Botanical Garden

Key West FL

StoryTime in the Garden

Celtic Conch Public House

The Studios of Key West

Glow Hours at Hugh's Views

Kitty Steadman at Margaritaville

Comedy Key West

Comedy Key West Open Mic

Dogwood Wellness Clinic!

Richie Allen at Kaya Island Eats

Richie Allen (Solo) at Kaya Island Eats

La Concha Key West, Autograph Collection 430 Duval Street Key West, FL 33040

Celebrate Halloween at the best bars across Duval Street with welcome shots/treats, drink specials and more.
Key West's Halloween Bar Crawl is taking over Duval Street on Halloween eve.
Dress up, grab your crew and join one of Key West’s biggest Halloween nightlife events, featuring 5+ of the city’s best bars in one of its most popular neighborhoods. Costumes make the perfect icebreaker, so come ready to mix and mingle for an even more memorable Halloween experience.
🎃 One Ticket. One District. One Huge Halloween Night. Your wristband gives you access to participating venues across the district, up to 5 complimentary welcome shots and other perks. Choose your own route, bounce from bar to bar and see where the night takes you.
🧡 Bring your friends and save 20% on group tickets of four or more! Tickets are limited and prices go up as we sell out, so get yours early before they're gone.

MANDATORY CHECK-IN BETWEEN 5PM–8PM: 📍 La Concha Key West, Autograph Collection — 430 Duval St, Key West, FL 33040

WHAT'S INCLUDED 🔶 Up to 5 Complimentary Welcome Shots/Treats – Redeem at the bars of your choice (limit 1 per venue) 🔶 Signature Halloween Drink Specials – Curated for the occasion 🔶 Free Cover – At all participating venues (no re-entry at some locations) 🔶 Professional Event Photography – You bring the look, we’ll capture the moment 🔶 Instagram Costume Contest – Post your look, tag us, and win

HOW IT WORKS 1. Check in between 5–8PM at La Concha Key West, Autograph Collection. 2. Collect your wristband, bar map and event perks. 3. Choose your route and crawl in your own time, there is no set schedule. 4. Sip, dance, mingle, repeat. It’s your Halloween, your way.
 For updated participating bars &amp; restaurants please click on link below <a href="https://www.eventbrite.com/cc/halloween-bar-crawls-2026-key-west-fl-4868829" rel="nofollow noopener" target="_blank">eventbrite.com/cc/halloween-bar-crawls-2026-key-west-fl-4868829</a>
 COSTUME CULTURE 👻 You don’t need to go full theatrical, but this night is about the look. Make it iconic, creative, stylish - or simply bold. 📸 Post your best shot on Instagram and tag @downtowncrawlers to enter the contest. Winners will be announced the week after the crawl.Happens on the following Dates: Oct 30, 2026, 5:00pm to Oct 31, 2026, 12:00am Timezone: Eastern Time (US &amp; Canada) Oct 31, 2026, 4:00pm to 11:30pm Timezone: Eastern Time (US &amp; Canada)<a href="https://eventvesta.com/events/166426/t/tickets" target="_blank" rel="nofollow noopener">View Tickets &amp; More Info</a>

Local Event: Halloween Bar Crawls 2026 - Key West, FL

Monroe County

Key West

Florida

Halloween Bar Crawls 2026 - Key West, FL

Celebrate Halloween at the best bars across Duval Street with welcome shots/treats, drink specials and more.
Key West's...

The Marker Key West Harbor Resort

Spend Sunday afternoon poolside at <a href="https://www.themarkerkeywest.com/" rel="nofollow noopener" target="_blank">The Marker Key West Harbor Resort</a> with a free live concert and pool party featuring <a href="https://robbentonofficial.com/" rel="nofollow noopener" target="_blank">Rob Benton</a> on Sunday, November 1, from 4-7 p.m.
Known for blending percussion, looping, beatboxing, rock and hip-hop influences into his acoustic performances, Benton will bring his signature sound to The Marker’s palm-filled pool deck.&nbsp;
Guests can enjoy live music, poolside entertainment and the resort’s laid-back Key West atmosphere throughout the evening.

Local Event: Rob Benton Concert and Pool Party at The Marker Key West Harbor Resort on November 1

Rob Benton Concert and Pool Party at The Marker...

Spend Sunday afternoon poolside at The Marker Key West Harbor Resort with a free live concert and pool party featuring Rob...

Rob Benton Concert and Pool Party at The Marker Key West Harbor Resort on November 1

Celebrate the excitement of Key West's 45th annual Race World Offshore World Championship at<a href="https://www.themarkerkeywest.com/" rel="nofollow noopener" target="_blank"> The Marker Key West Harbor Resort</a> on Saturday, November 7, from noon to 4 p.m. Hosted in partnership with <a href="https://goodboyvodka.com/" rel="nofollow noopener" target="_blank">Good Boy Vodka</a>, the poolside celebration invites guests to soak up the sunshine amid the resort’s tropical grounds, while enjoying snacks, product samples and swag! Additional information can be found at&nbsp; <a href="https://www.themarkerkeywest.com/location/calendar" rel="nofollow noopener" target="_blank">https://www.themarkerkeywest.com/location/calendar</a>

Local Event: Powerboat Week Party at The Marker Key West Harbor Resort on November 7

Powerboat Week Party at The Marker Key West...

Celebrate the excitement of Key West's 45th annual Race World Offshore World Championship at The Marker Key West Harbor Resort...

Powerboat Week Party at The Marker Key West Harbor Resort on November 7

Join The Sanctuary Sailing—a premium, fully affirming LGBTQIA+ (non)holiday cruise group setting sail from Miami from December 21 to 26, 2026. 
We sail onboard Virgin Voyages adults-only ship, the Scarlet Lady, to Cozumel, Mexico and Bimini, Bahamas. Enjoy luxury made-to-order dining, free Wi-Fi, fitness classes, and festival-style entertainment!
Exclusive Group Perks Included:
- An intimate, private Meet and Greet.
- A $100 Bar Tab for premium drinks.

Group Registration Update
The deadline for group rates has passed, but we are still accepting new reservations! Reservations are now based on the best available rate at the time of your request. 
Let us make this winter holiday one to remember—surrounded by community and luxury.
Full itinerary: <a href="https://hanksmart.com/editorial/sanctuarycruise" rel="nofollow noopener" target="_blank">hanksmart.com/editorial/sanctuarycruise</a>

Local Event: LGBTQIA+ Sanctuary Cruise: Miami to Cozumel & Bimini

LGBTQIA+ Sanctuary Cruise: Miami to Cozumel &...

Join The Sanctuary Sailing—a premium, fully affirming LGBTQIA+ (non)holiday cruise group setting sail from Miami from December...

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