Weekend Guide: October 9-11, 2026

Executive Summary. Columbus Day weekend in the Florida Keys is anchored by the America 250 Seven Mile Bridge Sunset Celebration, a community celebration of America's 250th birthday at the Old Seven Mile Bridge in Marathon on Saturday, October 10. Around it, the SOMO Half Marathon and 10K in Key West, Bike MS: Breakaway to the Keys, the Lower Keys Rotary Fall Festival and Haunted House, and the Hurricane Cup fishing tournament round out a full weekend across the islands, with Taste the Keys running all month long in the Upper Keys.

The Big Event: America 250 Seven Mile Bridge Sunset Celebration

The centerpiece of the weekend is the America 250 Florida Keys: 7 Mile Bridge Sunset Celebration, a major community celebration commemorating America's 250th birthday. Here is what to know before you head to the bridge:

• Saturday, October 10, from 5:00 to 7:30 PM at the Old Seven Mile Bridge in Marathon.
• Sunset around 7:05 PM, timed to the heart of the celebration.
• Live music and local food, including food from the Marathon High School Culinary Program and Grimal Grove.
• History and cultural programming celebrating America's 250th birthday.

Friday, October 9

Friday opens a full weekend across the islands, from a community fall festival in the Lower Keys to ghost stories and a drag show in Key West:

• Lower Keys Rotary Fall Festival & Haunted House (October 9-11, Lower Keys): A community fall festival and haunted-house event hosted by the Lower Keys Rotary, one of the main local events running throughout the weekend.
• Marathon Community Theatre Fundraising Gala featuring Jaimie Roberts (October 9, 6:00 PM to October 10, 9:00 PM, Marathon): A fundraising gala benefiting Marathon Community Theatre, featuring entertainer Jaimie Roberts.
• Feed the Keys Food Drive / Drop-Off (October 9, 2:00-6:00 PM, Marathon): A community food-drive event benefiting local residents.
• Ghost Stories from the Gardens (8:30-9:30 PM, Key West Tropical Forest & Botanical Garden): A nighttime ghost-story tour featuring stories and legends connected to the Florida Keys, with proceeds benefiting CFK Academy students.
• Hush Money, a drag show (8:30-10:30 PM, Hush Hush Theatre, Key West): A live drag and performance event hosted by Beatrix Dixie.
• Hurricane Cup captains meeting, Friday, October 9, 7:00 PM at the Islamorada Fishing Club.

Saturday, October 10

Saturday is the weekend's peak, when the 7 Mile Bridge Sunset Celebration draws the islands together at the Old Seven Mile Bridge in Marathon. The rest of the day's lineup keeps the momentum going across the Keys:

• America 250 Florida Keys: 7 Mile Bridge Sunset Celebration (5:00-7:30 PM, Old Seven Mile Bridge, Marathon): Live music, local food, and history and cultural programming celebrating America's 250th birthday, with sunset around 7:05 PM and food from the Marathon High School Culinary Program and Grimal Grove.
• Bike MS: Breakaway to the Keys (October 10-11, Key Largo and Keys route): A two-day cycling event benefiting the National Multiple Sclerosis Society, with opportunities for people to participate or volunteer.
• Lower Keys Rotary Fall Festival & Haunted House (Lower Keys): Continues through Saturday.
• Hurricane Cup tournament fishing, 8:00 AM to 3:30 PM, Islamorada, benefiting the Guides Trust Foundation Hurricane Relief Fund, which supports members of the Keys inshore fishing community.
• If The Shoe Fits: Key West National Finals, 8:00 PM at 724 Duval Street, Key West. Regional winners compete in the Key West National Finals, with the winner earning a title connected to the New Year's Eve High Heel Shoe Drop. No cover, but RSVP is required. 21 and older.
• Boondocks Open-Air Market, 9:00 AM to 2:00 PM at Boondocks Grille & Draft House on Ramrod Key. More than 20 local vendors including artists, jewelry makers, farmers and plant vendors, with food and live music.
• Upper Keys Sons & Daughters of Italy Wine Tasting, 6:00 PM at the Key Largo Civic Club. Celebrates Italian Heritage Month with wine tasting and Italian food catered by the Italian Food Company of Key Largo. $20 per person, with proceeds benefiting local charities.

Sunday, October 11

Sunday closes the weekend with a waterfront race in Key West and the final day of several events still running across the islands:

• SOMO Half Marathon & 10K (Key West): A waterfront running event featuring a half marathon and 10K through Key West. The official Florida Keys calendar lists it as a confirmed event for October 11.
• Bike MS: Breakaway to the Keys (Florida Keys): Continues Sunday, October 11.
• Lower Keys Rotary Fall Festival & Haunted House (Lower Keys): Final day of the October 9-11 event.
• Hurricane Cup tournament fishing, 8:00 AM to 3:30 PM, followed by the barbecue and awards ceremony at 5:00 PM at the Islamorada Fishing Club.
• Florida Keys Farmers Market, 10:00 AM to 3:00 PM at Islamorada Gardens Plaza, 81001 Overseas Highway. Local produce, handmade products, artisan goods and small businesses.

All Month Long: Taste the Keys

Running October 1 through 31 in Key Largo and the Upper Keys, Taste the Keys is a month-long culinary celebration featuring participating restaurants, special prix-fixe menus, local ingredients, chef experiences, tasting events, and other food-focused activities.

Visitors on October 9 through 11 can easily weave Taste the Keys into their weekend, pairing a festival day in Marathon with a special meal in the Upper Keys along the way.