Florida Keys Weekend Guide: October 31–November 2, 2026
Halloween, Día de los Muertos and Powerboat Racing
Saturday, October 31 through Monday, November 2, 2026
Looking for things to do in the Florida Keys this Halloween weekend? From waterfront costume parties in Islamorada to live music throughout Key West, cultural celebrations and the opening of Race World Offshore, October 31 through November 2 offers a mix of entertainment, island traditions and boating excitement.
This weekend is especially appealing for visitors who want to experience more than one side of the Keys. You can enjoy a sunset dinner in the Upper Keys, explore Key West's music scene, celebrate Día de los Muertos and watch the opening activities of one of the area's major offshore powerboat events.
Here's what to know before planning your weekend.
Saturday, October 31: Halloween Across the Florida Keys
Halloween in the Florida Keys offers several ways to celebrate, from waterfront live music to late-night masquerade parties and family-oriented neighborhood activities.
1. Halloween at Lorelei Restaurant & Cabana Bar: Islamorada
Saturday, October 31 · 5-9 p.m.
Location: 96 Madeira Road, Islamorada
Lorelei Restaurant & Cabana Bar is hosting Brothers of Others for an evening of live music, costumes and waterfront entertainment beside Florida Bay.
The event is open to the public, with no entertainment cover charge listed by the official tourism calendar. Arrive early if you want to enjoy the sunset before the evening gets underway.
Best for: Couples, groups of friends and visitors who prefer live music with a relaxed waterfront atmosphere.
Event details and updates
2. Masquerade on the Bay at Pierre's: Islamorada
Saturday, October 31 · 9 p.m.-1 a.m.
Location: 81600 Overseas Highway, Islamorada
For a more upscale Halloween evening, Pierre's at Morada Bay is hosting a masquerade-themed celebration featuring music, a DJ, photo opportunities and a costume contest scheduled for 11:30 p.m.
The official listing describes the event as free admission and restricted to guests aged 21 and older. Confirm entry requirements and any event updates before attending.
Best for: Adults looking for a dress-up event, music and a distinctive waterfront setting.
Official event listing3. Neighborhood Halloween Activities: Marathon
Families staying around Marathon can also look for neighborhood-oriented Halloween activities, including Gulfside Village Trick or Treat, Grassy Key Halloween and the traditional behind-the-airport trick-or-treating area.
Local event information has noted traffic control around the behind-the-airport activity during the evening. Check the latest local announcements for the confirmed schedule, access arrangements and parking instructions before taking children out.
Best for: Families looking for a neighborhood Halloween experience rather than a late-night party.
4. Trop Rock'N Duval: Key West
October 28-November 1 · Multiple venues
Location: Key West, including Old Town and Duval Street venues
Trop Rock'N Duval brings island-inspired music to venues throughout Key West. The festival's published program describes more than 60 performances across 23 venues, with a mix of intimate shows, theater performances and live music around Old Town.
On Halloween Saturday, check the schedule for individual performances, ticket requirements and venue times before choosing where to spend the evening.
Best for: Music lovers and travelers who want to combine Halloween with Key West nightlife.
Official Trop Rock'N Duval scheduleSunday, November 1: Día de los Muertos and Race World Offshore
Sunday brings together cultural celebration and high-speed marine action, with events in both Islamorada and Key West.
5. Día de los Muertos Celebration: Islamorada
Sunday, November 1 · 3-6 p.m.
Location: Florida Keys Brewing Company, 81611 Old Highway, Islamorada
The Florida Keys Brewing Company beer garden is scheduled to host a Día de los Muertos celebration centered on memory, music and dance. The event provides a cultural alternative to the weekend's Halloween parties.
Día de los Muertos, or Day of the Dead, is a tradition in which families and communities remember and honor loved ones who have died. Its cultural significance makes this event a meaningful addition to the weekend's activities.
Best for: Visitors interested in cultural traditions, music and community events.
Official Florida Keys events calendar
6. Race World Offshore Key West World Championship
November 1-8 · Key West
Main location: Truman Waterfront Park and Key West Harbor
The Race World Offshore Key West World Championship begins Sunday, November 1, and continues through November 8. The event brings high-performance offshore racing boats to the waters around Key West for a major week of competition.
Sunday's opening activities include the World's Fastest Boat Parade, scheduled for approximately 4 p.m. Key West city records authorize a rolling street closure for the parade at that time. Check official announcements for the current route and traffic arrangements.
Best for: Boating enthusiasts, families, photographers and visitors interested in marine events.
Where can you watch the races?
The official tourism guide identifies several viewing areas:
- Truman Waterfront Park and Race Village
- Fort Zachary Taylor Historic State Park
- Mallory Square
- Sunset Pier
- Simonton Street Beach
Viewing access, admission and visibility vary by location. Check the official event information before traveling, and follow instructions from race officials and local authorities.
Official Race World Offshore visitor informationBoating tip: If you plan to watch from the water, use an authorized spectator operator or follow official spectator guidance. Observe race-area restrictions and maintain a safe distance from the course.
Monday, November 2: More Ways to Enjoy Key West
If you're extending your stay into Monday, you can trade the weekend crowds for a more relaxed day of sightseeing, dining and evening entertainment.
7. Glow Hours at Hugh's Views
5-7 p.m. · The Studios of Key West
This rooftop event is listed on the Florida Keys tourism calendar for November 2, with sunset views, art and live music. Verify the latest event details before making plans.
Official event information
8. Catch the Mania Trivia
6:30-8:30 p.m. · Key West Cooking Show
This recurring trivia night covers pop culture, history, food and Key West trivia. The venue is listed at 291 Front Street, Suite 207, near Mallory Square. Reservations are suggested.
Official event listing
9. Monday Night Jazz Jams
8:30-11:30 p.m. · William Weech American Legion Post 168
The weekly jazz jam hosted by pianist Larry Smith features local and visiting musicians. It is a good option for visitors who prefer live music in a community setting.
Address: 803 Emma Street, Key West.
Florida Keys events calendarLast Chance: Taste the Keys Ends October 31
If food is part of your weekend plans, Saturday, October 31, is the final scheduled day of the 2026 Taste the Keys culinary celebration.
The monthlong event highlights participating restaurants in Key Largo and the Upper Keys with special menus and dining experiences. Some offers may require advance reservations or have specific service times, so check the current participating restaurant list before making plans.
Best for: Food lovers who want to try local restaurants and make the most of the final day of the event.
Official Taste the Keys information
Suggested Three-Day Itinerary
Here's one way to organize the weekend. Since Islamorada and Key West are separated by a considerable drive, it may be more practical to choose one area each day rather than attempt every event.
SAT
Oct 31
Halloween in the Upper Keys
- Morning: Enjoy breakfast and explore the waterfront.
- Afternoon: Visit Islamorada or relax by the water.
- 5-9 p.m.: Halloween at Lorelei.
- 9 p.m.-1 a.m.: Pierre's Masquerade on the Bay, if eligible and interested.
Alternative: Stay in Key West for Trop Rock'N Duval and Halloween performances.
SUN
Nov 1
Culture and powerboat racing
- Morning: Have brunch or take a waterfront walk.
- 3-6 p.m.: Attend Día de los Muertos in Islamorada, or choose Key West's opening-day powerboat activities.
- Around 4 p.m.: The World's Fastest Boat Parade is scheduled in Key West.
Planning note: These afternoon events overlap geographically and partly in time. Choose one area or allow sufficient travel time rather than attempting both.
MON
Nov 2
A relaxed day in Key West
- Morning: Explore Old Town or enjoy a leisurely breakfast.
- Afternoon: Visit a local attraction or watch the harbor.
- 5-7 p.m.: Glow Hours at Hugh's Views.
- 6:30-8:30 p.m.: Catch the Mania Trivia.
- 8:30-11:30 p.m.: Monday Night Jazz Jams.
Check event schedules and travel between venues before finalizing the evening.
Where to Stay for Halloween Weekend
Choosing your base can make a significant difference to your weekend.
- Key Largo: Convenient for Upper Keys activities, boating and reef excursions.
- Islamorada: A strong choice for waterfront dining, Halloween events and fishing.
- Marathon: A central base for exploring the Middle Keys and driving north or south.
- Key West: Best suited to visitors prioritizing Trop Rock'N Duval, nightlife and Race World Offshore.
Accommodation can be in high demand around major events. Check cancellation policies, parking and driving plans before booking.
Explore our community guides for more information about each area:
- Key Largo
- Islamorada
- Marathon
- Key West
FAQs
Frequently Asked Questions
What is happening in the Florida Keys on Halloween weekend 2026?
When does Race World Offshore start in Key West?
Where can I watch the Key West powerboat races?
Is there a Día de los Muertos event in the Florida Keys?
Should I stay in Key West or Islamorada?
Resources
Official Resources
Related Guides
Helpful Guides
Key Largo Community Guide
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Islamorada Community Guide
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Marathon Community Guide
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Big Pine Key Community Guide
Quiet nature-filled Lower Keys living, home to the National Key Deer Refuge.
Lower Keys Community Guide
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The Conley Group Florida Blog
More weekend guides, market updates and Keys lifestyle stories from Steve Conley.
Ready to Take the Next Step?
Weekends like this one are why so many visitors end up calling the Keys home. If you are thinking about making the Florida Keys your everyday, Steve Conley can help you find the right place, from Key Largo to Key West.
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