Key West Half Marathon & 5K, 8K, 10K, Rum Stroll & Beer Mile

Which race is on which day

The weekend is split in two. On Saturday, the 5K and the 10K start and finish at Higgs Beach on Atlantic Boulevard.¹³ On Sunday, the half marathon and the 8K start at the corner of Caroline Street and Trumbo Road, less than two blocks from packet pickup.¹³

Half marathon runners must be in position by 6:30 a.m.¹ The Hemingway Rum Stroll and the Key West Beach N' Beer Mile follow on Sunday afternoon.⁵

The event falls on Martin Luther King Jr. Day weekend, and the organizers advise booking hotels early.⁷

The half marathon course

The half marathon runs up Duval Street, past the Southernmost Point and along Smathers Beach, and finishes behind Waterfront Brewery.⁴ The organizers say most of the race is adjacent to the ocean.¹

There are about 10 aid stations, with water at the start, at the finish and approximately every 2 miles.¹ The race is cup free, so runners need to carry their own bottle to refill.¹ Ultima Replenisher is available from the second water station.²

Pace groups are offered at 1:40, 1:50, 2:00, 2:10, 2:20, 2:30, 2:45 and 3:00, and runners can be tracked through the RaceJoy app.³

Time limits

The half marathon finish line stays open for four hours, until 11:00 a.m.² The 8K and the 10K each have a two-hour limit.²

The 5K has a strict one-hour limit, which ends at 8:00 a.m.² That is also when the 10K starts.¹ Runners who do not finish the 5K in time can still take part in the 10K, but they will not be officially timed for it.²

The Big Pecker and Lil' Pecker challenges

The two challenges let runners race on both days. The Big Pecker Challenge is the half marathon, the 10K and the 5K, and it earns four medals including a special challenge medal.⁶ The Lil' Pecker Challenge is the 5K, the 8K and the 10K, and it earns three medals and a hat.⁶

Challenge runners use the same bib for every race and collect the challenge medal or hat at the Pecker Tent on Sunday after finishing, with their bib.¹ Runners doing more than one distance get one race shirt and a finisher medal for each distance.²

Expo and packet pickup

The expo and packet pickup are outside the Half Shell Raw Bar at 231 Margaret Street. For 2027 the hours are Friday, January 15, from 2:00 to 7:00 p.m.¹²

A late bib-only pickup runs from 7:15 to 10:00 p.m. on Friday at Fit2Run, 211 Duval Street.¹ There is no on-site registration on race day.²

Parking and race morning

Parking near the Sunday start is limited, and the organizers strongly suggest arriving by taxi, rideshare or bicycle.² Bag check is open from 6:00 to 6:45 a.m. on race day.¹

What runners get

All participants receive a race shirt, a finisher medal, a race bag, food and drinks, rum tasting and entry to the race party.⁶

Awards go to the top three men and women overall and in the masters division, and three deep in age groups that run from 1 to 9 up to 75 and over.²

The organizers note that USA Today readers voted the race one of the 10 best half marathons in the nation in 2023 and 2025.⁴

Rules and registration policies

• Headphones and AirPods are not permitted, because the roads are not fully closed to traffic. Runners who use them may be disqualified.²
• There are no refunds. Deferrals to 2028 closed on October 1, 2026.²
• The deadline to edit a registration, including switching distance, is January 1, 2027.²
• A registration can be moved to the virtual event from your RunSignup account, and every race has a virtual option.²⁶
• Rum Stroll and Beer Mile entries are forfeited if you do not arrive with your bib on Sunday.¹