Something comes down Duval Street most months of the year, and a good share of it passes the corner on our cameras. This calendar lists the annual events worth tuning in for. Dates move from year to year, so check with the organizers before you plan a trip around one.
| When | Event | On our cams? |
|---|---|---|
| January | Key West Food and Wine Festival, Key West Half Marathon | Busier sidewalks |
| Late April | Conch Republic Independence Celebration | Yes. Parade, drag race and bed races on Duval |
| Late April to early May | Key West Songwriters Festival | Crowds between venues |
| Early June | Key West Pride | Yes. Street fair and parade on Duval |
| Early July | Key Lime Festival | Busier sidewalks |
| Third week of July | Hemingway Days | Yes. Look-alikes and the Running of the Bulls at Sloppy Joe’s |
| August | Key West Lobsterfest | Yes. Street fair on Duval |
| Late October | Fantasy Fest | Yes. Saturday night parade on Duval |
| November | Key West Powerboat Races | Race-week crowds |
| Early December | Holiday Parade | Parade through Old Town |
| December 31 | New Year’s Eve | Yes. Conch shell drop at Sloppy Joe’s |
January through March is when Key West is fullest. The weather is dry, highs sit in the mid to upper 70s, and the sidewalks on our cameras are busy from mid-morning on. January brings the Key West Food and Wine Festival and the Key West Half Marathon.
Conch Republic Independence Celebration. On April 23, 1982, Key West seceded from the United States for about a minute, in protest at a Border Patrol roadblock. The town has marked the anniversary ever since with roughly ten days of events around that date. Three of them happen on Duval Street: a drag race, in which performers in heels sprint a block of the street; the bed races; and a parade billed as the world’s longest because it runs the full length of Duval, from the Atlantic to the Gulf. The story of the secession is in our history of Duval Street.
Key West Songwriters Festival. For five days in late April and early May, more than 200 songwriters play around 50 shows in bars, theaters and hotel courtyards across the island, many of them on or near Duval.
Key West Pride fills the first part of June with a street fair and a parade on Duval.
The Key Lime Festival takes over the week of the Fourth of July in honor of the island’s signature pie.
Hemingway Days runs for six days around July 21, the author’s birthday. The main event is the Hemingway Look-Alike Contest at Sloppy Joe’s, which reached its 45th year in 2026. The final round is on Saturday night. That afternoon the contestants stage the “Running of the Bulls” outside the bar with wooden bulls on wheels. Both of our cameras have a front-row view.
Key West Lobsterfest celebrates the opening of Florida’s lobster season in August with a street fair on Duval.
September is the slowest month of the year and the peak of hurricane season. It is the one time you are likely to see the sidewalks on our cameras half empty at night.
Late October belongs to Fantasy Fest, Key West’s ten-day costume festival, which ends with a Saturday night parade down Duval. November brings the offshore powerboat races and the first of the winter visitors.
The Holiday Parade rolls through Old Town early in the month.
New Year’s Eve is the biggest night of the year on our cameras. Duval Street closes to traffic, and by 11 p.m. it is packed. Key West lowers its own things at midnight instead of a ball. These are the three best known:
A parade takes a while to travel the length of Duval, so the picture can stay quiet for some time and then fill all at once. If you miss the moment, the Cam Archive holds a snapshot of every minute for the following 24 hours.
