Clermont this weekend: the Great Floridian Triathlon and its 15K and 5K at Waterfront Park, the downtown Wine Stroll Saturday and Mike Masse live Friday.

The Great Floridian Triathlon takes over Waterfront Park this weekend, with its 15K and 5K on Saturday morning, the downtown Wine Stroll Saturday night and a classic rock concert Friday.

Last checked Oct. 15, 2026. Times and prices are as each organizer publishes them, linked with each entry. Free means the organizer says free.

Friday, Oct. 16

  • Story Time for Kids, 10:30 and 11:30 a.m., Minneola Library, 302 W. Pearl St., Minneola. Singing, dancing and a short story, aimed at ages 5 and under; both sessions are the same. Lake County Library System.
  • Mike Masse: Epic Acoustic Classic Rock Concert, 7 to 9 p.m., Clermont Performing Arts Center, on the Arts and Recreation Center campus at 3700 S. U.S. 27. The YouTube cover artist plays acoustic classic rock. Tickets on the show page; also on the city calendar.

Saturday, Oct. 17

  • Floridian 15K and 5K, 7:30 a.m. (15K) and 7:35 a.m. (5K), Waterfront Park. Sommer Sports’ road races open the triathlon weekend; packet pickup runs 6 to 7:30 a.m. Entry fees are on the registration page.
  • MTG Commander League, 9:30 a.m. to 12:30 p.m., Friends’ Room, Cooper Memorial Library, 2525 Oakley Seaver Drive. A social Magic: The Gathering league in the Commander format. Lake County Library System.
  • Weekly Scavenger Hunt, all day, children’s room at Cooper Memorial Library. Pick up a clue sheet at the children’s desk and hunt for hidden characters and objects. Lake County Library System.
  • Downtown Clermont Wine Stroll, 6:30 to 9 p.m., rain or shine, check-in at 756 W. Montrose St. Red, white and rose tastings at more than 20 downtown businesses for ages 21 and older, with a glass, wristband and map at check-in. Tickets from Clermont Main Street.

Sunday, Oct. 18

  • Great Floridian Triathlon, from 7:30 a.m., Waterfront Park. The sprint triathlon, aquabike and aquathlon start at 7:30 a.m., the sprint duathlon at 7:32 a.m. and the Triple Triathlon, three sprint triathlons back to back, at 7:45 a.m. Registration for most events stays open until 11:59 p.m. race day on the race page. Schedule and parking: our Great Floridian Triathlon page.
  • Downtown Clermont Farmers Market, 9 a.m. to 2 p.m., 752 W. Montrose St. Produce, handmade goods and baked treats in the heart of downtown; free to visit. Clermont Main Street.

All weekend

  • Fall Festival at Southern Hill Farms, 16651 Schofield Road. Friday 11 a.m. to 8 p.m.; Saturday and Sunday with reserved arrival times. Corn maze, pumpkin patch, wagon rides, fire pits and a kids fun zone. Tickets must be bought online in advance for everyone 3 and older, and the farm is cashless. Southern Hill Farms. More in fall festivals and pumpkin patches.

Regular weekend fixtures

  • Clermont Historic Village, 490 West Ave., Saturdays and Sundays, 1 to 4 p.m.; free during regular hours. Clermont Historical Society.
  • Downtown Clermont Farmers Market, every Sunday, 9 a.m. to 2 p.m. See farmers markets.

Driving downtown or along the lakefront on Sunday morning? Check the triathlon’s bike course and our road construction and closures page. For the rest of the month, see things to do this month and arts and exhibitions.

Send us your event

Email hello@clermontpost.com with the date, time, venue, price and a photo. Listings are free and go on this page and in our events diary.

Frequently asked questions

What is there to do in Clermont this weekend?

Mike Masse plays the Clermont Performing Arts Center Friday, Oct. 16. The Floridian 15K and 5K run Saturday morning and the Wine Stroll fills downtown that evening. The Great Floridian Triathlon is Sunday at Waterfront Park, alongside the farmers market downtown.

What is free in Clermont this weekend?

The Downtown Clermont Farmers Market is free to visit Sunday, 9 a.m. to 2 p.m., and the Clermont Historic Village is free during its regular hours, 1 to 4 p.m. Saturday and Sunday.

What time does the Great Floridian Triathlon start?

Sunday, Oct. 18: the sprint triathlon, aquabike and aquathlon at 7:30 a.m., the sprint duathlon at 7:32 a.m. and the Triple Triathlon at 7:45 a.m., all from Waterfront Park. The 15K and 5K start Saturday at 7:30 and 7:35 a.m.