Events & Exhibits
From annual traditions and cultural events to special exhibits and community programs, join us throughout the year to explore, celebrate, and connect with Key West's history.
Front Row to the Icons
Exclusive Porch Party!
For one unforgettable evening, the front porch of The Oldest House will be one of the most exclusive places in Key West as it becomes the setting for a private parade-viewing experience.
Award-winning Chef Juan Cuadra of Salty Chef Catering will present an exclusive collection of beautifully prepared small bites created especially for this occasion. Guests will also enjoy a top-shelf bar that includes a selection of fine wines and the warm hospitality of a privately hosted evening.
October 24, 2026 (Saturday)
322 Duval Street, Key West
Doors Open: 6:30pm
$500 per guest
Strictly limited to 20 guests
Questions: 305-294-9501
Slow Passage of Time
Five-Course, Wine-Paired Culinary Experience
Step inside the Oldest House after dark for an intimate evening of exceptional food, fine wine, and nearly 200 years of Key West history.
Your evening includes:
Five-course dinner prepared by an award-winning chef
Wine pairing with each course
Full-service dining
An exclusive experience inside the Oldest House Museum & Tom Majors Garden
An evening surrounded by nearly 200 years of Key West history
October 29, 2026 (Thursday)
322 Duval Street, Key West
Reception: 6:00pm || Dinner: 7:00pm
$200 per guest
Strictly limited to 10 guests
Questions: 305-294-9501
67th Annual
Key West Home Tours
A rare invitation into Key West’s private historic homes.
For four special months each year, local homeowners open their doors to share the beauty, history, and stories of their private residences. Each month features four distinctive historic homes, plus a special visit to The Oldest House Museum, offering guests an unforgettable glimpse inside the island’s hidden architectural gems.
Home Tour Dates:
December 29-30, 2026 (Tues & Wed)
January 22-23, 2027 (Fri & Sat)
February 12-13, 2027 (Fri & Sat)
March 12-13, 2027 (Fri & Sat)
64th Annual
Conch Blowing Contest
Make Some Noise!
The annual Conch Blowing Contest brings together locals and visitors for a one-of-a-kind island tradition. Open to contestants of all ages, the event features friendly competition, food, drinks, music, and a full day of fun in the sun at The Oldest House Museum & Tom Majors Garden
2027 Date Coming Soon!
Free community event
ART, MUSIC, BASEBALL: ONE KEY WEST STORY
Exhibit
By combining seemingly disparate Conch traditions, like art and baseball, we discover how varying interests can intersect in unique and whimsical ways.
Discover art by Cuban-American artist and Key West native, Julie Arroyo, mother of MLB All-Star and musician, Bronson Arroyo. Cuban contemporary caricaturist, Reynerío Tamayo. Plus baseball bat art by Key West locals.