Calendar

Clermont events

What’s on in Clermont and next door. Times from the city and downtown calendars.

Clermont First Friday → Family Food Fest

Clermont Main Street moved the old First Friday food trucks to first Saturdays as Family Food Fest (4–8 p.m., 8th between Minneola & Montrose + Montrose from Lake to West). Free to walk; trucks and vendors rotate.

October’s was Sat Oct 3. Next: Saturday, November 7, 2026.

Sources: clermontdowntown.com/events · clermontfl.gov/254/Events

Events in Clermont this weekend · Oct 16–18

Heads-up for both mornings: the Great Floridian race weekend is at Waterfront Park, so expect runners on the South Lake Trail Saturday and triathletes in the lake Sunday. Fun to cheer; give yourself extra time near the lake.

Friday–Sunday · October 16–18

9:00 a.m.–7:00 p.m.

Family

Showcase of Citrus / Pumpkin Ponderosa

15051 Frank Jarrell Rd. · Clermont

Haunted monster truck rides select nights, 7:45–10:15 p.m. (ages 12 and up).

Source: showcaseofcitrus.com

Friday–Sunday · October 16–18

Fri 11 a.m.–8 p.m. · Sat 9 a.m.–8 p.m. · Sun 9 a.m.–7 p.m.

Family

Southern Hill Farms Fall Festival

16651 Schofield Rd. · Clermont

Tickets online in advance. Ages 3 and up; under 3 free.

Source: southernhillfarms.com

Friday, October 16, 2026

7:00–9:00 p.m.

Mike Massé: Epic Acoustic Classic Rock

PAC Mainstage, 3700 S. Highway 27 · Clermont

Tickets through the PAC.

Source: clermontperformingarts.com

Saturday, October 17, 2026

7:30 a.m.

Family

Clermont Waterfront Parkrun

Lake Hiawatha Preserve · Clermont

Free 5K. Check parkrun.us/cancellations before you go.

Source: parkrun.us/clermontwaterfront

Saturday, October 17, 2026

7:30 a.m.

Floridian 15K & 5K

Waterfront Park · Clermont

Great Floridian race weekend. 15K at 7:30 a.m., 5K at 7:35 a.m., out and back on the South Lake Trail.

Source: Great Floridian on TriSignup

Saturday, October 17, 2026

8:30 a.m.–12:30 p.m.

Family

Birdwatching by Bike

Van Fleet Trail, 7450 Bay Lake Rd. · Groveland

$10, ages 6 and up. Register through the city.

Source: groveland-fl.gov

Saturday, October 17, 2026

10:00 a.m.–5:00 p.m.

Corks & Forks

Lakeridge Winery, 19239 U.S. 27 N · Clermont

Free admission; tastings $5. Winery hours otherwise are Monday–Saturday 10 a.m.–5 p.m., Sunday 11 a.m.–5 p.m., last tour at 4.

Source: lakeridgewinery.com

Saturday, October 17, 2026

6:30–9:00 p.m.

October Wine Stroll

Check-in 756 W. Montrose St., on the Art Walk · Clermont

$25. Photo ID required. Check-in from 5:30.

Source: clermontdowntown.com

Sunday, October 18, 2026

from 7:30 a.m.

Great Floridian Triathlons

Waterfront Park · Clermont

Race morning on the lake, including the Triple Tri, starting around 7:30.

Source: Great Floridian on TriSignup

Sunday, October 18, 2026

9:00 a.m.–2:00 p.m.

Family

Downtown Clermont Farmers Market

752 W. Montrose · Clermont

Weekly.

Source: clermontdowntown.com/events

Sunday, October 18, 2026

11:00 a.m.–5:00 p.m.

Corks & Forks, Day Two

Lakeridge Winery · Clermont

Free admission.

Source: lakeridgewinery.com

Coming up

Saturday, October 24, 2026

noon–2:30 p.m.

Thursday, October 22, 2026

7:00 p.m.

Teens Got Talent Showcase

PAC · Clermont

Teens Got Talent Showcase at the PAC.

Source: clermontfl.gov calendar

Friday, October 23, 2026

7:00–9:00 p.m.

Divas of Soul

PAC · Clermont

Divas of Soul at the PAC.

Source: clermontfl.gov calendar

Clermont Woman’s Club Fashion Show

Gabby’s Banquet Hall · Clermont

$35.

Source: South Lake Tablet

Tuesday, October 27, 2026

6:30–8:30 p.m.

Family

Saturday, October 24, 2026

4:00–6:00 p.m.

Groveland & Mascotte Meet the Candidates

Puryear Building, 243 S. Lake Ave. · Groveland

Groveland and Mascotte city council candidates, then an auction for local history preservation.

Source: South Lake Tablet

Sunday, October 25, 2026

7:00–9:00 p.m.

Ahmad Doo Wop Tour

PAC · Clermont

Ahmad Doo Wop Tour at the PAC.

Source: clermontfl.gov calendar

Scaremont — Halloween on the Trail

Waterfront Park · Clermont

Free. Trick-or-treat stations, a costume contest, and Hotel Transylvania at 7 p.m.

Source: clermontfl.gov Events

Friday, October 30, 2026

4:30–7:30 p.m.

Family

Wednesday, October 28, 2026

5:00–8:00 p.m.

Minneola Market & Food Trucks

City Hall Gym · Minneola

Fourth Wednesday market and food trucks.

Source: minneola.us

Groveland Trunk or Treat

Cherry Lake Park · Groveland

October’s 2nd Friday stand-in. There is no 2nd Friday Block Party in October. Next 2nd Friday is Friday, November 13.

Source: groveland-fl.gov

Saturday, October 31, 2026

10:00 a.m.–4:00 p.m.

Family

Clermont Harvest Festival

752 West Montrose Street · Downtown Clermont

Clermont Main Street’s fall Saturday: vendors, kids’ activities, live music, and a costume contest. Free admission.

Source: clermontdowntown.com/events

Saturday, October 31, 2026

5:30–8:30 p.m.

Family

Minneola Safe Night Out

Minneola Trailhead Park · Minneola

City safe-night event at the trailhead.

Source: minneola.us

Saturday, November 7, 2026

4:00–8:00 p.m.

Family

Thursday, November 5, 2026

5:00–8:30 p.m.

Taste of South Lake & Business Expo

Waterfront Park · Clermont

$40.

Source: South Lake Tablet

Family Food Fest

Downtown Clermont · Clermont

Next first-Saturday food trucks downtown (4–8 p.m.). October’s was Sat Oct 3.

Source: clermontdowntown.com/events

Saturday, November 7, 2026

10:00 a.m.–4:00 p.m.

Family

Mascotte Founders Day

Mascotte

Founders Day, 10 a.m. to 4 p.m.

Source: South Lake Tablet

Friday, November 13, 2026

5:00–9:00 p.m.

Friday, November 13, 2026

November Wine Stroll

Downtown Clermont · Clermont

November Wine Stroll downtown.

Source: clermontdowntown.com/events

Groveland 2nd Friday Block Party + Veterans Day

Lake David Park · Groveland

The next 2nd Friday. There is no 2nd Friday in October.

Source: groveland-fl.gov calendar

Friday, December 4, 2026

Family

Annual Tree Lighting

City Hall Park / Downtown Clermont · Clermont

Light Up Clermont at City Hall Park.

Source: clermontfl.gov Light Up Clermont

Saturday, December 5, 2026

10:00 a.m.

Family

Clermont Christmas Parade

Starts at Waterfront Park, loops downtown · Clermont

Floats, bands, and local groups. Starts at Waterfront Park.

Source: clermontfl.gov Christmas Parade

Saturday, December 5, 2026

2:00 p.m.

Family

Minneola Centennial Celebration

Trailhead Park · Minneola

Minneola turns 100.

Source: minneola.us calendar

Calendars

Recurring Sunday markets stay on the downtown calendar at 9 a.m.–2 p.m. unless Main Street posts a change.