11/25/2025
❤️💚Season’s greetings! 💚❤️The holidays are upon us and this community knows how to celebrate!
🎄 Nov. 26- Lighting of the Harbor Walk- 6 p.m. - Historic Seaport; Holiday music starts at 5 p.m.
🎅 Nov. 28- Breakfast with Santa - 9-11 a.m. - St Peter the Fisherman Catholic Parish Big Pine - $5 per person
🛠️ Nov. 29 - Kids Workshop Teddy Bear Ornament - 9 a.m.-noon - Home Depot
🌀 Nov. 30 - Conch Republic Navy Hurricane Flag Burning Ceremony - 4 p.m. - Truman Waterfront
🎄Nov. 30 - 3rd Annual Lighting of Ocean’s Edge Christmas Lobster Trap Tree - 4 p.m.- 7 p.m.
🎄 Nov. 30 - City of Key West Tree Lighting - 6 p.m. - Bayview Park
❤️ Dec 1 - Handel’s Messiah Concert - 7 p.m. - Key West United Methodist Church (600 Eaton Street)
🎬 Dec. 3 - Kiki’s Sandbar Family Movie Night - 7 p.m. - ELF
❤️ Dec. 4 - MWR WinterFest- 4 p.m. - 7 p.m. - Sigsbee Community Center - MUST be MWR authorized
📚 Dec. 5 - Grinch Party - 3:30-5 p.m. - Marathon Public Library
❄️ Dec. 5 - BeLighted Bike Ride - 8 p.m. & Holiday Village - 4-9 p.m. - Coffee Butler Amphitheater (register online) www.WesleyHouse.org/BeLighted2025
🛠️ Dec. 6 - Kids Workshop Holiday Cocoa Mug - 9 a.m.-noon - Home Depot
❤️ Dec. 6 - Sugarloaf School Holiday Craft Show - 9 a.m.-2 p.m.
💚 Dec. 6- Key West Hometown Holiday Parade - 7 p.m. - Kicks off at Bayview Park and travels along Truman Avenue and Duval Street
🎒Dec. 7 - LOCALS DAY
🏅Dec. 7- Montessori Key West 5K & Kids Fun Run - 8 a.m. - Truman Waterfront Park - contact The Children’s School to register https://www.facebook.com/share/1BZF5wzWuy/?mibextid=wwXIfr
❤️ Dec. 7- Eaton Street Christmas Stroll - 3:30-7 p.m. kickoff at Key West United Methodist Church
💚 Dec. 7 - Women’s Club Holiday Open House - 4:30-6:30 p.m. - Hellings-Curry Museum (319 Duval Street)
🚂 Dec. 8 & Dec. 11 to Dec. 23- Conch Tour Train Holiday Sights and Festive Nights Tours - Multiple nightly tours depart from Key West H.S.
❤️ Dec. 8 to Dec. 23 - Old Town Trolley Holiday Lights & Sights Tours - Multiple nightly tours begin at Mallory Square
🎬 Dec. 10- Kiki’s Sandbar Family Movie Night - 7 p.m. - The Grinch
💚 TBD- MCFD Holiday Parade - Stock Island & Key Haven
❤️ TBD- MCFD Holiday Parade - Big Coppitt & Bay Point
💚 TBD- MCFD Holiday Parade - Sugarloaf, Cudjoe & Summerland
❤️ TBD- MCFD Holiday Parade - Ramrod & Little Torch
💚 TBD- MCFD Holiday Parade - Big Pine
🎄 Dec. 12 - Holiday Concert & Bazaar (Free) - 5-9 p.m. - Key West Museum of Art & History at the Custom House (281 Front Street)
💚 Dec. 12 & 19- Holiday Historic Inn Tours - 6-8 p.m. - Explore four beautifully decorated Key West locations and their unique architecture and history - https://keystix.com/
🏅 Dec. 13 - A Positive Step 5K Rudolph Red Nose Run - 7 a.m. - check-in and 8 a.m. start time - Beginning and ending at Southernmost Beach Café (1405 Duval Street)
🐴 Dec. 13 - Island Time Stables 5th Annual Holiday Hoedown- 1-3 p.m.- Cudjoe Key
❤️ Dec. 13- Key West Artisan Market’s Merry Marketplace- 4 p.m.- 8 p.m. - Southernmost Beach Resort (1317 Duval St)
⛵️Dec. 13 - Stock Island Holiday Lighted Boat Parade & Carnival- Carnival begins at 3 and Boat Parade at 6:30 p.m. - The Perry Hotel and Marina-Key West Rotary Club
⛵️ Dec. 13- 34th Annual Lighted Boat Parade - 8 p.m. - Key West
🐄 Dec. 14 - Monroe County Sheriff’s Office Christmas on the Farm - 1-3 p.m. - College Road, Stock Island
🕎 Dec. 14- City of Key West Menorah Lighting Ceremony - 5 p.m. - Bayview Park
🎬 Dec. 17 - Kiki’s Sandbar Family Movie Night - 7 p.m. - Home Alone
🎅 Dec. 20 & 21 - Breakfast with Santa - 9 a.m. to noon- Hard Rock Cafe
🎬 Dec. 24- Kiki’s Sandbar Family Movie Night - 7 p.m. - Santa Claus
🎶 Dec. 30 - Mike Stack & Friends Concert - 6 p.m. - Blue Flamingo Backyard
