Friday October 16 – Sunday October 18, 2026
A wine weekend, mostly, with plenty for the kids around it. Friday is classic rock on acoustic guitar at the PAC. Saturday and Sunday, Lakeridge has its first Corks & Forks out on the vineyard green, and Saturday night is the October Wine Stroll downtown. Sunday morning is the Montrose market.
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 · October 16
7:00–9:00 p.m.
Clermont Performing Arts Center Mainstage · 3700 S. Highway 27
Mike Massé returns with Sterling Cottam: big acoustic takes on the Beatles, Simon & Garfunkel, Elton John, Rush, and Toto. Yes, that “Africa” cover. Tickets through the PAC.
Source: clermontperformingarts.com
Fri–Sun
FamilyFri 11 a.m.–8 p.m. · Sat 9 a.m.–8 p.m. · Sun 9 a.m.–7 p.m.
16651 Schofield Rd.
Corn maze, wagon rides, a petting zoo, a pumpkin barn, u-pick sunflowers and zinnias, and apple cider donuts. Buy tickets online before you go, ages 3 and up; under 3 free. Weekend tickets come with an arrival time.
Source: southernhillfarms.com
Open all weekend
Family9:00 a.m.–7:00 p.m. daily
15051 Frank Jarrell Rd.
Pumpkins and photo spots on the citrus ranch, plus monster trucks, gem mining, and animals. After dark on select nights, the Haunted Monster Truck Rides run 7:45–10:15 p.m. (ages 12 and up; book ahead).
Source: showcaseofcitrus.com
Saturday · October 17
Family7:30 a.m.
Lake Hiawatha Preserve · 450 N. Lake Minneola Shores
Free weekly timed 5K. Walk, jog, run, or volunteer. Register once at parkrun.us and bring your barcode. Check parkrun.us/cancellations — the Great Floridian is on the lake trail that morning.
Source: parkrun.us/clermontwaterfront
Saturday · October 17 · Great Floridian race weekend
15K at 7:30 a.m. · 5K at 7:35 a.m.
Clermont Waterfront Park · 100 3rd St.
Flat out-and-back on the South Lake Trail. Sunday morning is the triathlons, including the Triple Tri, starting around 7:30.
Source: Great Floridian on TriSignup
Sat–Sun
FamilySat 10 a.m.–5 p.m. · Sun 11 a.m.–5 p.m.
Lakeridge Winery & Vineyards · 19239 U.S. 27 N
The winery’s first Corks & Forks: food trucks, art and craft vendors, free cornhole, and live music on the outdoor stage. Saturday is The Old Skool Band, then the Mike Quick Band; Sunday is Dave Capp & France Neil, then The Essentials. Free to get in; wine tastings are $5. Bring lawn chairs.
Source: lakeridgewinery.com
Saturday · October 17 · Groveland
Family8:30 a.m.–12:30 p.m.
Van Fleet Trail · 7450 Bay Lake Rd., Groveland
A guided ride on the Van Fleet with stops to spot and identify Florida birds. Bring your own bike; e-bike rentals are available through a local partner (352-404-8342). $10 a person, ages 6 and up. Register through the city.
Source: groveland-fl.gov
Saturday · October 17
6:30–9:00 p.m. (check-in from 5:30)
Check-in: 756 W. Montrose St., on the Art Walk
Red, white, and rosé at 20-plus downtown businesses. Pick up your glass, wristband, and map at check-in, then wander. $25, online or in person; in-person sales close at 8. Photo ID required. Rain or shine.
Source: clermontdowntown.com
Sunday · October 18
Family9:00 a.m.–2:00 p.m.
752 West Montrose Street
Produce, baked goods, crafts; downtown shops open around it.
Source: clermontdowntown.com/events
Sunday · October 18
11:00 a.m.–5:00 p.m.
Lakeridge Winery
Dave Capp & France Neil until 1:30, then The Essentials until 5. Free admission.
Source: lakeridgewinery.com
No Family Food Fest this weekend. The next first-Saturday Food Fest downtown is Saturday, November 7, 4–8 p.m. Free to walk; trucks rotate month to month.
Source: clermontdowntown.com/events
North of town
19239 U.S. 27 N, Clermont
Saturday Oct 17, 10 a.m.–5 p.m. · Sunday Oct 18, 11 a.m.–5 p.m.
Lakeridge has been pouring Florida muscadine on the hills north of town since 1989, and this is its first Corks & Forks. It’s a lawn-chair kind of day: four bands across the weekend on the outdoor stage, food trucks, local art and craft vendors, and cornhole under the shade trees. Getting in is free and tastings are $5. Regular tours and tastings run every day — Monday–Saturday 10 a.m.–5 p.m., Sunday 11 a.m.–5 p.m. — with the last tour at 4.
Members
$3.92
Updated Oct 13
Members
$3.869
Updated Oct 13
Eat
Confirm at the table. Prices move.
Every day · dine-in
$11.99
2523 U.S. 27
9-inch pizza (up to five toppings) and a half Caesar or Italian salad.
Monday–Friday · 3–6 p.m.
$5
2523 U.S. 27
Pints of local beer, glasses of wine, and craft breadsticks.
Boar's Head Ultimate Sub · $9.49 (was $11.49)
Whole · roast beef, ham & turkey · through Wednesday, Oct 14