Key West, Florida (United States of America) - "Key West Half Marathon and Runfest". Key West, Florida | Saturday, January 16 to Sunday, January 17, 2027 | Half Marathon, 10K, 5K, 8K and Fun Runs. Rated as one of the top 15 scenic half marathons in North America by Runner's World and a top 10 half marathon by USA Today, the Key West Half Marathon and Runfest provides the opportunity for runners and walkers to take on a half marathon, 10K, 8K, 5K, Papa's Pilar Rum Stroll, the Key West Beach N Beer Mile, the Big Pecker Challenge, and the Lil Pecker Challenge. The half marathon, 10K, 8K, and 5K routes take participants along the scenic Key West waterfront with views of the ocean throughout. Participants of the Big Pecker Challenge will take part in the 5K, 10K, and half marathon, receiving medals for all three races in addition to a Big Pecker Challenge medal. Those who take part in the Lil Pecker Challenge will participate in the 5K, 8K, and 10K distances and will be awarded a medal for each distance run, as well as a one-of-a-kind Lil Pecker Hat. The Papa's Pilar Rum Stroll will take participants across six popular locations in Old Town Key West with a Papa's Pilar Rum drink to enjoy at each stop, while the Informal Beer Mile will feature an untimed fun run on the Southernmost Beach with four beers. After completing the mile run and tasting four beers, participants will be rewarded with awards for several categories and raffles. Thousands of runners are expected to take part in the festivities over the weekend. Packet pickup - Half Shell Raw Bar: Friday, Jan. 15, 2 - 7 p.m.; Saturday, Jan. 16, 1 - 6 p.m. Race times: Saturday, Jan. 16, 7 a.m. - 5K start time, 8 a.m. - 10K start time. Sunday, Jan. 17, 7 a.m. - half marathon start time, 7:30 a.m. - 8K start time, 1 - 5 p.m. - Papa's Pilar Rum Stroll, 3 p.m. - Beach N Beer Mile start time. Participant perks: custom race T-shirts, custom medals, various prizes for costume contests and raffles. Awards will be presented to the top three overall male and female finishers, top three master male and female finishers, and top three male and female finishers in each age group. https://go.evvnt.com/3582665-0?pid=6562

Masaryktown, Florida (United States of America) - "Masaryk Wine Run 5k". Like Running or Walking? Love Wine? This race is for you! Join us on Saturday, January 16, 2027 at 10:00am for an exciting event that features the scenic views of Masaryk Winery. Their Wines are made on site from the fruit they grow and from other Florida Farms! So, whether you are looking to run, walk or just enjoy the wine this race is a sure thing for a great time and an incredible experience! This race is timed and scored by J3 Timing. Results will be posted at www.J3Timing.com. Registration Includes: * T-shirt : Super Soft Ring Spun Cotton t-shirt included! * Wine Glass : Shatterproof, Collapsible, and Portable! * Finisher Medal: Doubles as a Wine Stopper! * Race Bib : Chip timed 5k run/walk * Results Posted Online * ...and of course, a pour of wine! https://runsignup.com/Race/FL/Masaryktown/MasarykWineRun5k?aflt_token=Nktw0AUB3nF4FPeh7Y7AWqQewFdw9sGt

West Palm Beach, Florida (United States of America) - "Outlast Miami". What Is OUTLAST? OUTLAST is a 6-hour, 12-hour, or 24-hour trail endurance challenge where runners complete a 5K every hour, on the hour. Each lap must be finished within the hour to stay in the event. If you finish early, you rest until the next round. Miss a lap, and you're out. Complete all six or twelve, or twenty-four rounds, and you OUTLAST. https://runsignup.com/Race/FL/WestPalmBeach/OUTLASTMIAMI?aflt_token=Nktw0AUB3nF4FPeh7Y7AWqQewFdw9sGt

Kissimmee, Florida (United States of America) - "Formosa Spiked Apple 5k". Join us on Sunday, March 14, 2027 8:30am and 10:30am (you will pick your start time during registration) for a fun event that features the amazing scenery and landscape of Formosa Winery! This location might look like a big house in a field... but they are actually a tasting house on a large expanse of property that consists of a vineyard and various fruit orchards! Come inside to find a unique central Florida dining destination and memorable wine tasting experience to both locals and tourists alike. They have 50 wines from around the world on tap and are located just 2 miles from Walt Disney World, Orlando Florida and directly across the street from Margaritaville. So, whether you are looking to run, walk or just enjoy the cider and camaraderie this race is a sure thing for a great time and an incredible experience! https://runsignup.com/Race/FL/Kissimmee/FormosaSpikedApple5k?aflt_token=Nktw0AUB3nF4FPeh7Y7AWqQewFdw9sGt