January 2027 Key West Events & Festivals

Plan your Key West trip with this calendar of January 2027 events, festivals, concerts, and things to do.

  • The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band — January 1, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Live Music)
  • Sunset Celebration — January 1, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Sunset Celebration — January 2, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Keller Williams Trio featuring Gibb Droll & Jason Hann — January 2, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Scott Kirby - 36 YEARS OF SONGS AND STORIES with Noah Robertson — January 2, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Scott Kirby - 36 YEARS OF SONGS AND STORIES with Noah Robertson — January 3, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — January 3, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Sunset Celebration — January 4, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Ben Harrison — January 5, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — January 5, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Key West Literary Seminar — January 6, 2027 · San Carlos Institute: An annual gathering of writers, readers, and literary enthusiasts featuring discussions, workshops, and readings. (Browse group: Arts & Culture)
  • Brian Patafie (9:00PM) — January 6, 2027 · 9:00 PM (Doors 8:30 PM) · Back Stage Listening Room (Browse group: Community)
  • Sunset Celebration — January 6, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Brian Patafie (7:00PM) — January 6, 2027 · 7:00 PM (Doors 6:15 PM) · Back Stage Listening Room (Browse group: Community)
  • Key West Art Walk — January 7, 2027 · Various Galleries on Duval: A monthly event where local galleries open their doors for an evening of art, wine, and conversation. (Browse group: Food & Drink)
  • Sunset Celebration — January 7, 2027 · Mallory Square: A nightly celebration featuring local artists, musicians, and street performers as the sun sets over the Gulf. (Browse group: Live Music)
  • Brian Patafie — January 7, 2027 · 8:00 PM (Doors 7:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Key West Literary Seminar — January 7, 2027 · San Carlos Institute: An annual gathering of writers, readers, and literary enthusiasts featuring discussions, workshops, and readings. (Browse group: Arts & Culture)
  • Key West Farmers Market — January 7, 2027 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring fresh produce, local crafts, and artisanal products from the Florida Keys. (Browse group: Food & Drink)
  • Key West Artisan Market — January 8, 2027 · 10:00am - 2:00pm · Higgs Beach: A market featuring local artisans and their crafts, held in a beautiful outdoor setting. (Browse group: Food & Drink)
  • Key West Literary Seminar — January 8, 2027 · San Carlos Institute: An annual gathering of writers, readers, and literary enthusiasts featuring discussions, workshops, and readings. (Browse group: Arts & Culture)
  • Scott Kirby - 36 YEARS OF SONGS AND STORIES — January 14, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • Key West Half Marathon — January 15, 2027 · 7:00am: A scenic half marathon through the beautiful streets of Key West, attracting runners from all over. (Browse group: Sports)
  • Kash'd Out — January 16, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Ben Harrison — January 19, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)
  • The Phil Collins Experience — January 20, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Classic Seger: Bob Seger's Greatest Hits Live (6PM) — January 23, 2027 · 6:00 PM (Doors 5:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Classic Seger: Bob Seger's Greatest Hits Live (9PM) — January 23, 2027 · 9:00 PM (Doors 8:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • The Jayhawks — January 25, 2027 · 8:00 PM (Doors 7:00 PM) · Key West Theater (Browse group: Arts & Culture)
  • Scott Kirby - 36 YEARS OF SONGS AND STORIES with Larry Smith — January 28, 2027 · 7:00 PM (Doors 6:00 PM) · Back Stage Listening Room (Browse group: Community)