Key West Holiday Fest Lights Up Seaport, Community Begins Monthlong Celebration

Key West kicked off its holiday season on the evening of Wednesday, Nov. 26, 2025 as the Chamber of Commerce and city partners launched a month of seasonal events on the Historic Seaport and around the island. Before sunset a countdown culminated in the 6:00 p.m. lighting of the giant Fishing Buoy Christmas tree and the opening of the 20th annual Harbor Walk of Lights at Greene Street Plaza and Lazy Way Lane. At 7:00 p.m. the Lobster Trap Christmas tree at Margaret Street Plaza was lit, and the public was invited to bring toys for the Cheryl Cates Toy Drive.

The festival runs through Dec. 31 with illuminated palm trees, ships and seasonal displays along the Historic Seaport. Events this season include an outdoor Black Friday shopping lineup on Nov. 28 at Truman Waterfront Park featuring the Key West Artisan Market, Truman Waterfront Farmers Market and Mom and Pop Key West vendors. The Studios of Key West hosts a Holiday Makers Market on Nov. 29 with artists, do it yourself ornament painting and local craft vendors. City organized celebrations continue on Sunday, Nov. 30 with a tree lighting ceremony at Bayview Park and an evening concert that ushers in ongoing community activities through December. The Chamber post lists additional community holiday events and provides links for scheduling and participation. The MARC annual Christmas tree lot will operate from Nov. 28 through Christmas Eve at 1401 Seminary Street.

For Monroe County residents the festival is more than seasonal décor. The concentrated schedule of markets and performances supports local small businesses and artisans, particularly independent vendors who rely on holiday foot traffic. Events that emphasize local makers and mom and pop businesses can help keep revenue within the community, and charitable elements such as the Cheryl Cates Toy Drive and the MARC tree lot add social support during a time of need.

At the same time the influx of visitors and increased local foot traffic present logistical and public health considerations for a small island community. Crowded late evening events can strain transportation systems, emergency services and sanitation resources. Accessibility for residents with mobility limitations, safe routes for families and planning for weather related impacts are practical concerns that city planners and community groups will need to address as programming unfolds.

As the lights and music draw residents and visitors alike, collaboration between the Chamber, city officials, local vendors and social service organizations will determine whether the festival delivers an inclusive celebration that boosts the local economy while protecting public safety and serving the county's most vulnerable residents.