The Reilly Arts Center's stand-up comedy showcase Friday night is the weekend's sharpest ticket -- three live comics on one stage for $25. Pair that with a free classical concert at Mount Dora's library Saturday featuring violinist Qing Li and pianist Victor Santiago Asuncion, and you've got a weekend that covers a lot of ground. Weather-wise, all three days run the same Florida script: bright, sunny mornings, low-90s heat, and a fair chance the sky throws an afternoon tantrum. Do the outdoor stuff early and let the storms have the back half of the day.
Friday
Amaya -- KC Wine Bistro
KC Wine Bistro is billing this one as a free night of amazing music, and Amaya is the act delivering it. Crystal River's a haul for some, but if you're already in the area this is a no-brainer evening out.
Mark Raisch at Yellow Pony -- World Equestrian Center
Mark Raisch takes the stage at the Yellow Pony inside World Equestrian Center. WEC's venues tend to draw a laid-back after-dinner crowd, and the Yellow Pony is one of the more relaxed spots on the campus to catch live music on a Friday.
Movie Nights at The Riding Academy Hotel Pool -- World Equestrian Center, Complimentary for hotel guests
If you're staying at the Riding Academy Hotel this weekend, the pool movie night is included -- no extra cost. It's a genuinely good perk for a Florida evening when the storms have moved on and the air has cooled down a bit.
Open Pickleball -- Clermont Arts & Recreation Center Gymnasium, 11:30 AM & 6:00 PM ET
Two sessions Friday -- a midday one at 11:30 AM and an evening session at 6:00 PM. Bring a photo ID (required for entry), wear athletic shoes with non-marking soles, and leave the sandals at home. Kids under 14 need an adult with them at all times.
The Edge Of Rock -- Sawgrass Grove, Free, 5:00 PM ET
The Edge of Rock is a Villages homegrown band -- high-energy classic rock and crowd favorites, out on the town square. Free admission, open air, no reservation needed. Good pick if you want to warm up the Friday evening before deciding where to land for dinner.
Osaka Fall -- Lake Sumter Landing, Free, 5:00 PM ET
Osaka Fall sets a different tone than your typical cover act -- their setlist pulls from rare old-school jams, glam rock, funk, modern pop, and soul, and they lean hard into stuff you won't hear every other weekend. Free on the town square at Lake Sumter Landing starting at 5:00 PM.
Johnny Wild & The Delights -- Spanish Springs Town Square, Free, 5:00 PM ET
If the '50s and '60s are your era, Johnny Wild & The Delights are the move Friday night. They describe themselves as a time machine back to classic music and style of that era, and Spanish Springs is the right backdrop for it. Free, outdoors, 5:00 PM.
May 2026 | The Marion Theatre Presents: Sit Down for Stand Up -- Reilly Arts Center, $25.00, 7:30 PM ET
Three comedians, one stage, seated show at the Reilly Arts Center. This is the most produced event of the weekend -- a proper theater comedy night at $25 a ticket. If you haven't been to the Marion Theatre yet, this is a solid reason to finally go. Curtain at 7:30 PM.
Saturday
Classical Music Concert featuring Violinist Qing Li and Pianist Victor Santiago Asuncion -- W T Bland Public Library, 11:00 AM & 1:00 PM & 2:00 PM ET
The Piatigorsky Foundation -- an organization specifically focused on bringing live classical music into everyday community spaces -- is presenting this one in partnership with the library. Violinist Qing Li and pianist Victor Santiago Asuncion perform, and then stick around afterward so you can meet them. The description notes it's free and open to the public with refreshments served. Multiple start times listed: 11:00 AM, 1:00 PM, and 2:00 PM -- confirm which session works best before you head out.
History on a Plate: Backyard Cookouts -- W T Bland Public Library, 11:00 AM & 1:00 PM & 2:00 PM ET
Chef Rian's monthly food history series tackles the backyard cookout this time around -- the history, the fun facts, and possibly some recipe sampling. Every attendee gets door prize tickets and a take-home recipe from the chef. No registration required, and it's sponsored by the GFWC Mount Dora Woman's Club.
English Conversation -- W T Bland Public Library, Free, 11:00 AM & 1:00 PM & 2:00 PM ET
The library runs this free weekly English practice session with volunteer facilitators -- all languages welcome, no registration needed. It's a genuinely welcoming program if you or someone you know is working on conversational English skills.
Chess Club -- W T Bland Public Library, Free, 11:00 AM & 1:00 PM & 2:00 PM ET
All ages welcome -- kids 8 and up with a parent or guardian, adults, beginners, and seasoned players alike. The library supplies the chess sets, but you can bring your own. No registration required, just show up.
Toddler Start Smart -- The City of Brooksville Parks & Recreation, 2:00 PM ET
This 7-week program is built for ages 2-5, focused on foundational movement skills through play -- throwing, catching, kicking, hitting, hand-eye coordination. It's open-entry within the 1.5-hour window, so you don't have to stay the whole time. The description recommends aiming for 30-45 minutes for the best experience. Parent or caregiver participation is part of it.
Sunday
Mount Dora Village Market -- Sunset Park, Free admission; food purchased separately, 9:00 AM ET
More than 70 vendors along the lakeside at Sunset Park -- local produce, artisan foods, fresh-cut flowers, and handmade crafts. This market runs weekly and it's one of the better Sunday morning reasons to make the drive to Mount Dora. Admission is free; bring cash or card for the vendors. Get there before the afternoon storm window opens up.
Sunday FunDay -- Brooksville Parks and Recreation, Free, 1:00 PM ET
Jerome Brown Community Center is hosting a family drop-in afternoon with games, crafts, STEM activities, sports equipment, soft play for the little ones, and music. The whole thing is free and designed to be come-as-you-are -- no registration, no schedule to stick to. Good option if the afternoon storms stay away and the kids need somewhere to burn energy.
The Full Lineup
Find all 53+ events this weekend at villacalalineup.com/events/.
Got a tip or event we should know about? Email [email protected]
