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The Weekend Lineup

April 17–19in & around Central Florida

Highs in the low 90s, sunny skies all weekend, and zero rain in the forecast. Clermont launches its first-ever jazz festival on the waterfront, Ocala throws an oyster fest downtown, and the Opry has three straight nights of tributes -- Vince Gill, Frankie Valli, and Jimmy Buffett. Grab the sunscreen and pick a direction.

By Amelia Early, Central Florida editor · Updated April 16, 2026
Fri

Friday

Fri time TBA

Dustin Jenkins and the OBO Band pay tribute to Vince Gill with a deep-catalog set -- "When I Call Your Name," "Go Rest High on That Mountain," and the hits in between. The 7:00 PM show is already sold out, but the 2:30 PM matinee still has tickets.

Fri 5:00-8:00 PM ET

Rocky and The Rollers have been a Villages institution for 27 years, and Brownwood pairs their Friday set with a car show from 5 to 8. Classic rock, classic cars, classic Villages Friday.

Fri time TBA
[Standing Still

Ben Frey does the modern-Elton experience -- the visuals, the swagger, the hits that span four decades. If you want a tribute show that actually feels like a concert, this is it.

Fri 7:30 PM ET

The Reilly's intimate "in the box" series brings Damon Fowler -- Florida blues guitarist who has shared stages with Dickey Betts and Derek Trucks both. Small room, big player. $28-$40.

Fri time TBA

Special dining experience during the $142,000 NSBA All-Age Open Trail Finals at the World Equestrian Center in Ocala. Price includes gratuity.

Sat

Saturday

Sat 3-9 PM ET
Waterfront Park, $10 GA / $40 premium seating

The first-ever Clermont Arts and Jazz Fest -- and they're going big right out of the gate. Saxophonist Walter Beasley headlines, with Grammy-winning drummer Sput Searight's band Ghost-Note rounding out the bill. Outdoor stage on the waterfront, local artists and vendors, and a $15 two-day pass if you're coming back Sunday. This is the headline event of the weekend.

Sat time TBA

All-day oyster festival in the Midtown Station food hall -- bites from every restaurant inside, live music by Peaches and the bands on rotation, and the full bar doing the work it was built for. Free admission; food and drinks purchased separately.

Sat time TBA

Saturday at the Opry, Four Seasons hits end to end. "Sherry," "Big Girls Don't Cry," "Walk Like a Man," all of it. Two shows -- matinee at 2:30 PM and evening at 7:00 PM.

Sat time TBA
[Villages Cruise-In

Monthly car show on the third Saturday, hosted by The Villages AACA. Classic cars 30+ years old, $5 per show car, free to spectate. Valve cover racing for the kids. Live entertainment on the square.

Sat time TBA
Renninger's, Mount Dora, free

One of the largest flea markets on the East Coast. Produce, antiques, vintage finds, collectibles -- the kind of place where you go for one thing and leave with four. Mount Dora institution, Saturday morning is the play.

Sat time TBA

1959 New England boarding school, Mr. Keating, "O Captain! My Captain!" -- a movie night at the Reilly for $5. Bring tissues.

Sat time TBA

Shelly Belly brings the social-media comedy act to the Marion for two nights. Quick-wit observational stuff -- her skits have pulled in millions of views online. Saturday is the show to go to if you want the better crowd energy.

Sun

Sunday

Sun 3-9 PM ET
Waterfront Park, $10 GA / $40 premium seating

Day two of the jazz fest. Chart-topping flutist Kim Scott and internationally acclaimed pianist Keiko Matsui share the waterfront stage. If you didn't grab the two-day pass Saturday, single-day Sunday admission is $10.

Sun 3:00 PM ET

The University of Florida Opera Theatre and UF Symphony Orchestra bring Gilbert and Sullivan to the Reilly -- the comic opera about a pirate apprentice who was supposed to be a ship's pilot. Silly, smart, and a Sunday matinee at 3 PM.

Sun 7:00 PM ET

Sunday night at the Opry, 7 PM, all Buffett. You know what you're getting.

Sun time TBA

"Survey says" style game show on the Eastport square. Teams of 4 can enter for on-site participation. Worth it for the crowd reactions alone.

That's the weekend.

See everything on in Central Florida — all weekend, all week.

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Updated April 16, 2026 · Times verified the week of publication; we surface what's really on — how The Lineup chooses.

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