| January |
Impromptu Concerts featuring Gryphon Trio |
| January |
Waterfront Playhouse - A Streetcar Named Desire |
| February |
Key West Symphony Orchestra |
| February |
Impromptu Concerts featuring Miami Strings |
| February |
Library Lectures < |
| February |
Leadership Monroe County Class X |
| February |
Cuban American Heritage Festival Cigar Dinner |
| February |
Heritage House Travel Writing Workshop |
| February |
TWFAC Founders Gala Event |
| February |
Heritage House Museum Tea & Conversation Program |
| February |
Take Stock in Children - Donors Forum |
| February |
Judy Drucker - Library Lecture |
| February |
"Flamenco Vivo" Carlota Santana - TWFAC |
| February |
Heritage House Museum Tea & Conversation |
| February |
Red Barn Theatre |
| February |
House & Garden Tour #2 |
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| Image from a Key West Garden Tour |
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| February |
Heritage House Travel Writing Workshop |
| February |
Gordon Ross & Friends |
| February |
Library Lecture |
| February |
Old Island Days Art Festival |
| February |
Impromptu Concerts featuring New Century Sax Quartet |
| February |
Red Barn Theater |
| February |
Library Lecture |
| March |
Heritage Days Festival |
| March |
Free Stroll Through Key West Botanical Gardens |
| March |
Key West Pops |
| March |
Library Lecture |
| March |
TWFAC Event |
| March |
House & Garden Tour #3 |
| March |
Impromptu Concerts |
| March |
Waterfront Playhouse |
| March |
Red Barn Theatre |
| March |
Conch Shell Blowing Contest |
| March |
Key West Woman's Club President's Ball |
| March |
Key West Garden Club Garden Tours |
| March |
Library Lecture |
| April |
Taste of Key West |
| April |
Key West Symphony Orchestra |
| April |
Key West Garden Club Spring Cleaning Sale |
| April |
Conch Republic Independence Celebration |
| April |
Red Barn Theatre - The Big Bang |
| April |
Annual Kick-Off Key West & Lower Keys Fishing Tournament |
| April |
Mel Fisher Maritime Museum Casino Night "Meet me in Hong Kong" |
| April |
Leadership Monroe County Class X |
| April |
Leadership Monroe County Class X Graduation |
| April |
Key West & Lower Keys Kick Off Tournament |
| April |
Key West & Lower Keys Fishing Tournament |
| May |
Relay For Life, American Cancer Society |
| May |
Waterfront Playhouse |
| May |
Key West Music Festival |
| May |
Minimal Regatta, Schooner Wharf Bar |
| June |
Gay Pride Week |
| June |
Super Boat Racing Series |
| June |
Cuban American Heritage Festival |
| June |
Key West International Jazz Festival |
| June |
Key West Theater Festival |
| June |
Key West Pops |
| July 4 |
Fireworks Celebration |
| July 4 |
Hospice 4th of July Picnic |
| July |
18th Annual Lower Keys Underwater Music Festival |
| July |
Geiger Key Marina Dolphin Tournament |
| July |
Hemingway Days Festival |
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| A Key West Event on Duval Street |
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| July |
Key West Marlin Tournament |
| July |
Key West Gator Club Dolphin Derby |
| July |
Mini Lobster Season |
| August |
Lobster Season |
| August |
Lobster Fest |
| August |
Miss Hawaiian Tropic - Key West Pagent |
| September |
Women Fest |
| September |
Poker Run - Bike Week |
| October |
Goombay Festival |
| October |
Fantasy Fest |
| November |
Key West Fishing Tournament |
| November |
Parrotheads in Paradise |
| November |
Key West Superboat World Championship |
| November |
APBA Offshore World Championship |
| November |
Pirates in Paradise |
| December |
Holiday House Tour |
| December |
Key West Lighted Boat Parade |
| December |
Annual Historic Seaport Music Festival |
| December |
World AIDS Day Annual Tree of Hope |
| December |
Key West Woman's Club Community Christmas Party |
| December |
Key West Holiday Festival - Helpline Benefit |
