Buckwheat International Ski Classic (Second Saturday of March). Annual cross-country ski race on groomed trails at Log Cabin, BC, organized by the Log Cabin Ski Society. Includes adult distances and a 5K for children; participants often race in themed costumes.
Skagway Spring Festival (April (mid-April; 2026 edition opened April 17)). Annual festival including the Skagway Arts Council's International Folk Festival, Spring Show of Winter Artwork, Disc Golf Tournament, and town-wide Clean Sweep litter cleanup.
North Words Writers Symposium (Late May). Annual creative-writing event featuring workshops, panel discussions, readings, and keynote Alaska-Northwest authors.
The Days of '98 Show (Mid-May through mid-September (daily performances tied to cruise-ship arrivals)). Klondike Gold Rush-themed musical theater show performed at Eagles Hall, Skagway, since at least the 1920s. Widely cited as Alaska's longest-running theatrical production. Depicts the story of Soapy Smith through…
Independence Day Street Party (July 4). Annual old-fashioned Independence Day celebration on Skagway's downtown streets with music, games, and street food.
Klondike Road Relay (September (2026 dates: September 11-12)). Annual 175 km running relay race starting in Skagway, Alaska and finishing in Whitehorse, Yukon. Broken into 10 legs; draws approximately 2,000 participants. Organized by Sport Yukon.
Skagway Fall Festival (October). Annual celebration of art, music, and community life in the north.
Skagway Yuletide Celebrations (First Friday of December through mid-December). Annual holiday celebration beginning with a tree lighting on the first Friday in December; includes artisan bazaars, quilt shows, photos with Santa, dances, open houses, and live music.