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Walking Events Calendar near Big Pine Key 2026-2027

Monthly updates for Big Pine Key

Get new running races (and updates) in your inbox every month.

Explore the top walking events near Big Pine Key for 2026-2027! We've gathered 4 great walks in the area. Check out our detailed list below to find your next local walk.

July 2026
Jul
25-26
Sa - Su

Hemingway Sunset Run 5K

Road Race Walk 3 mi
Walkers can choose the 3.1 Miles 5K walk that starts and finishes at the Southernmost Point Buoy, following an out and back course with a slight deviation. The route is flat and fast though heat and humidity may affect walkers, and there is an afte..
September 2026
Sep
5
Sa

Parrots and Margaritas 5K

Road Race Walk 3 mi
Walkers join the Parrots and Margaritas 5K Walk covering 3.1 Miles, starting and finishing at Kaya Island Eats on Duval Street in Key West. The walk runs alongside the 5K run and the untimed Flip Flop Mile and finishes near a post race gathering.
Sep
5
Sa

Hawks Cay Heroes Salute 5K Run/Walk

Road Race Walk 5 km
Walkers follow a 5K course through the island of Duck Key around Hawks Cay Resort, with packet pickup on the Marina Event Lawn. The event includes a timing chip and race T shirt and is limited to 200 participants.
October 2026
Oct
19
Mo

Fantasy Fest 5K

Road Race Walk 3 mi
Walkers follow Duval Street from the Tiki House Key West for 3.1 Miles, alongside the running races, and can join the post race party with a free drink.
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