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Free Key West holiday events in 2026, each with the source that says free

The short answer

These Key West, Florida, holiday events are listed as free for 2026: the Harbor Walk of Lights lighting (Nov. 25), the Schooner Wharf tree trimming party (Dec. 6), the Custom House concert and bazaar (Dec. 11), watching the Lighted Boat Parade from the Harbor Walk (Dec. 12), the Truman gingerbread build (Dec. 19) and the classic car show (Dec. 20). The Oldest House Museum is free daily.

By the Christmas in Key West Editorial Team5 min read Last checked October 21, 2026

A marina at sunset seen across the water: rows of moored sport-fishing boats and sailboats, wooden piers and pilings, a long low hotel building on the far shore, and a pale peach sky. It has a slightly grainy film look.
Photo: Herbert wie, CC BY-SA 4.0 (cropped)

“Free” gets used loosely in holiday roundups. For this list we kept to one test: the organizer, or the site that publishes the listing, has to use the word free for the 2026 event. If the page names no price at all, the event is not here, because silence about a price is not the same as free. Everything below was read on Oct. 21, 2026, and each entry names its source.

The free calendar, 6 dated events plus one daily

Wed. Nov. 25: Harbor Walk of Lights lighting
Sun. Dec. 6: Schooner Wharf tree trimming party
Fri. Dec. 11: Custom House holiday concert and bazaar
Sat. Dec. 12: Lighted Boat Parade, watched from the Harbor Walk
Sat. Dec. 19: Great Gingerbread Build at the Truman Little White House
Sun. Dec. 20: Holiday Classic Car Show and toy drive
Daily: Oldest House Museum, 322 Duval Street

The free events, in date order

Harbor Walk of Lights lighting, Wednesday, Nov. 25, 2026

keywestchristmas.org marks the lighting of the 21st Harbor Walk of Lights “Free”. Holiday music starts at 5:00pm and the Fishing Buoy Christmas Tree lights at 6:00pm at the Greene and Elizabeth Street plaza. The second lighting, the Lobster Trap Christmas Tree, follows at 7:00pm at the Margaret Street plaza in Old Lands End Village, according to the same site; the City’s notice for the night gives the marina address and a 6:00 to 7:30 PM window. Santa and Mrs. Claus hand out treats. Read more on the Harbor Walk of Lights page.

The night also starts the Cheryl Cates Toy Drive. Bring a toy, or buy one at the Imagination Station table and donate it there. Entry costs nothing; the toy is your call.

Schooner Wharf tree trimming party, Sunday, Dec. 6, 2026

Schooner Wharf lists “Rock Around Our Christmas Tree!” at 6:00 p.m., and keywestchristmas.org lists the 2026 Tree Trimming Party and Toy Drive the same evening, “FREE to Attend”. Food and drink at the bar are another matter.

Custom House holiday concert and bazaar, Friday, Dec. 11, 2026

The City’s notice gives 5:00 to 8:00 PM at the Custom House and Clinton Place, with Front Street closed from Greene to Whitehead. keywestchristmas.org calls it “This festive free party” and describes a holiday light show by Key West High School’s Conch 5 Studios projected on the face of the Custom House. The free wording is keywestchristmas.org’s; the Key West Art and Historical Society’s bazaar page talks about its animated projections and Festival of Trees. A bazaar is for buying, so bring a budget if you want to shop.

  • The City of Key West calendar lists "2026 Custom House Holiday Concert & Bazaar – City Property Event Notice" on "Friday, December 11, 2026", "5:00 PM – 8:00 PM": "The event takes place at the Custom House and Clinton Place. Front Street will be closed in front of the Custom House from Greene Street to Whitehead Street." KWAHS says students' trees will be displayed "in the week leading up to our Annual Holiday Concert & Bazaar on December 11th." City of Key West: Calendar event notice; Key West Art & Historical Society: Holiday Concert & Bazaar
  • keywestchristmas.org describes the Annual Holiday Concert & Bazaar at the Custom House, 281 Front Street, as "This festive free party" with "a holiday light show designed by Key West High School's Conch 5 Studios, which will be projected on the face of the Custom House." KWAHS's page mentions "Animated Holiday Projections" and its "Festival of Trees". Key West Art & Historical Society: Holiday Concert & Bazaar; keywestchristmas.org

Lighted Boat Parade from the Harbor Walk, Saturday, Dec. 12, 2026

The 35th parade has music from 6:00 and boats at 8:00pm. keywestchristmas.org says viewing runs all along the Harbor Walk at the Historic Seaport, with the reviewing stand at Schooner Wharf, and marks the listing FREE. It suggests coming early for music, dinner and drinks, and to see the boats at the dock. The seat on the Schooner Appledore II from 7:30 to 9:30 pm is a separate, very limited booking with no published price. The boat parade page has the full evening.

Great Gingerbread Build, Saturday, Dec. 19, 2026

The Truman Foundation’s event page for the second annual build says: “This event is free and open to the public.” It runs between 11:00am and 2:00pm, per the Foundation. The Holiday Fest calendar lists Dec. 19-20 from 1:00 to 3:00 pm; we go by the Foundation, which runs it.

Holiday Classic Car Show and toy drive, Sunday, Dec. 20, 2026

The Florida Keys Southernmost Car Club presents the 2026 show from 11:00am to 3:00pm in the Conch Republic Seafood Company parking lot, on the Harbor Walk of Lights at Greene Street. keywestchristmas.org marks it FREE, and like the lighting night it doubles as a toy drive.

Oldest House Museum, daily

The Old Island Restoration Foundation lists the Oldest House Museum at 322 Duval Street as “Open Daily” with general admission “Free”. The house was built circa 1829. It posts no Christmas Day note, so see our Christmas Day guide before planning a Dec. 25 visit.

  • OIRF Plan Your Visit: "Open Daily", "322 Duval St.", "General Admission" "Free". "Built circa 1829, The Oldest House Museum offers a glimpse into the people, architecture, and stories that shaped early Key West." Old Island Restoration Foundation: Plan Your Visit

Free for the youngest visitors

Some paid tickets have a free tier for small children, per each operator. The Hemingway Home lets children 5 and younger in free. On the Conch Tour Train holiday tour, ages 3 and under ride free on a parent’s lap; on Old Town Trolley’s holiday tour, ages 2 and under do the same. Everyone older pays the fares on the lights tours page.

  • Hemingway Home and Museum: "Museum is open daily, 365 days a year", "9:00am-5:00pm for walk-in visits", "Tours start every 15 minutes with the first tour starting at 9:15am". Adult "General Admission – $19"; "Children 5 and younger are FREE". Ernest Hemingway Home and Museum: Rates & Info
  • Conch Tour Train: "Prices starting at $32.25 for adults, $21.80 for kids (4-12)", "Ages 3 and under ride free (must ride on the parent/adult lap)." "Reservations required. Reservation-based tickets are non-refundable. You may reschedule up to 24 hours in advance of tour time." Phone "(305) 707-5775". Conch Tour Train: Holiday Sights and Festive Nights Tour
  • Old Town Trolley: "Adults: From $33.95*", "Children (3-12): $22.95*", "Ages 2 and under ride free. Must ride on parent's lap.", "*5% city fee added to all tickets". Departure times are not listed on the page. Old Town Trolley Tours: Key West Holiday Tours

Not on this list, and why

  • Pet Pictures with Santa, Dec. 3: $25 a picture, cash or Cash App, for the Boys and Girls Club.
  • City tree lighting (Nov. 30) and City menorah lighting (Dec. 6): the City’s notices give date, time and place and say nothing about price.
  • Fort Zachary Taylor: $6 per vehicle, per Florida State Parks.
  • OIRF Key West Home Tours, Dec. 29-30: $45 for museum members, $55 for non-members.
  • keywestchristmas.org: "Thursday, December 3", "6:00pm" to "8:00pm", "21st Annual Pet Pictures with Santa", "At the 16' Nautical Christmas Tree on the Harbor Walk of Lights at William St." and "Pictures with Santa are $25 (Cash and Cash App accepted) to benefit our local Boys & Girls Club." Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)
  • The City of Key West calendar lists "The City's Annual Christmas Tree Lighting Ceremony – City Property Event Notice" on "Monday, November 30, 2026", "6:00 PM – 8:00 PM", at "Bayview Park". City of Key West: Calendar event notice
  • The City of Key West calendar lists "The City's Annual Menorah Lighting Ceremony-City Property Event Notice" on "Sunday, December 6, 2026", "5:00 PM – 7:00 PM", at "Bayview Park". The Holiday Fest calendar lists the same ceremony 5:00 to 6:00 pm. City of Key West: Calendar event notice
  • Florida State Parks: Fort Zachary Taylor Historic State Park, "Hours 8 a.m. until sundown 365 days a year", "$6 per vehicle". "the park is the southernmost state park in the continental United States" and "boasts Key West's favorite beach, located at the southern end of the park, providing opportunities for picnicking, swimming, snorkeling, paddling and fishing." Florida State Parks: Fort Zachary Taylor Historic State Park
  • OIRF: "$45 per individual for museum member", "$55 per individual for non-museum member", "$180 package for all four months". "All ticket sales are final and non-refundable." Old Island Restoration Foundation: Key West Home Tours Info & FAQ

Two free weekends

Two pairs of free events sit on back-to-back days. Friday, Dec. 11, 2026 has the Custom House bazaar, and the next day, Saturday, Dec. 12, 2026, the boat parade. Saturday, Dec. 19, 2026 has the gingerbread build at the Truman Little White House, and Sunday, Dec. 20, 2026 the car show on the Harbor Walk. A visitor in town for either weekend can fill two days without a ticket.

If you drive, parking is a separate question. keywestchristmas.org points Harbor Walk visitors to the main lot at Margaret and Caroline, the garage at Caroline and Grinnell and the lot at Green and Elizabeth, and to its free scooter parking and bike racks. The parking page has the City garage rates.

  • keywestchristmas.org: "Park in the Main Parking Lot located at Margaret & Caroline St. OR the Parking Garage one block away at Caroline & Grinnell St. OR in the lot at Green & Elizabeth St." and "Please use FREE scooter parking areas and designated bike racks all around the Historic Seaport and Harbor Walk Area. Please no locking bikes to the decorations!" Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)

Sources we checked

How much is the Conch Train holiday tour?

Prices start at $32.25 for adults and $21.80 for kids 4 to 12. Ages 3 and under ride free on a lap. Tickets are non-refundable but can be rescheduled up to 24 hours ahead.

Source: Conch Tour Train: Holiday Sights and Festive Nights Tour

How much is the Old Town Trolley holiday tour?

From $33.95 for adults and $22.95 for children 3 to 12, plus a 5% city fee. Ages 2 and under ride free on a lap.

Source: Old Town Trolley Tours: Key West Holiday Tours

What is the BeLighted Bike Ride?

A lighted bike parade after the Holiday Village at the Coffee Butler Amphitheater on Friday, Dec. 4, 2026. The City notice gives the route: Amphitheater, Southard, Whitehead, Front, Duval, United, Whitehead and back. The Holiday Fest calendar says the ride departs at 8:00pm.

Source: City of Key West: Calendar event notice

Is there ice skating in Key West at Christmas?

The Coffee Butler Amphitheater describes a Waterfront Winter Wonderland with an ice skating rink, but its page gives no 2026 dates. keywestchristmas.org says it is closed Christmas Eve and Christmas Day.

Source: Coffee Butler Amphitheater: Waterfront Winter Wonderland

What holiday events are at the Truman Little White House?

The Truman Foundation lists a free Great Gingerbread Build on Saturday, Dec. 19, 2026, 11:00am to 2:00pm, and evening holiday house tours on Dec. 22 and 23 ($20 members, $35 non-members on Dec. 22).

Source: Key West Harry S. Truman Foundation: Events 2026

Written by the Christmas in Key West Editorial Team. We draft with help from AI tools; a person checks each fact against its source before it goes live.

Dates, rules and hours can change. The organisers have the final word: City of Key West: Visitors

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