The Weekend Lineup: April 17-19

**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.**

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## Friday

### [A Salute to the Music of Vince Gill starring Dustin Jenkins and the OBO Band](/events/a-salute-to-the-music-of-vince-gill-starring-dustin-jenkins-and-the-obo-band-2026-04-17-14-30/) -- [Orange Blossom Opry](/directory/orange-blossom-opry/), $25 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.

### [Rocky and The Rollers | Car Show](/events/rocky-and-the-rollers-car-show-500-pm-800-pm-2026-04-17/) -- [Brownwood Paddock Square](/directory/brownwood-paddock-square/), 5:00-8:00 PM ET, free [Rocky and The Rollers](/bands/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.

### [Standing Still -- A Tribute to Elton John](/events/standing-still-elton-john-tribute-mount-dora-2026-04-17/) -- [Mount Dora Music Hall](/directory/mount-dora-music-hall/), from $25 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.

### [Blues in the Box: Damon Fowler](/events/blues-in-the-box-damon-fowler-reilly-2026-04-17/) -- [Reilly Arts Center](/directory/reilly-arts-center/), 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.

### [A Sudden Impulse Dining Experience](/events/a-sudden-impulse-dining-experience-2026-04-17/) -- [World Equestrian Center](/directory/world-equestrian-center/), $160 per person Special dining experience during the $142,000 NSBA All-Age Open Trail Finals at the [World Equestrian Center](/directory/world-equestrian-center/) in Ocala. Price includes gratuity.

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## Saturday

### [Clermont Arts and Jazz Festival: Walter Beasley & Ghost-Note](/events/clermont-arts-and-jazz-festival-walter-beasley-ghostnote-2026-04-18/) -- [Waterfront Park](/directory/waterfront-park/), $10 GA / $40 premium seating, 3-9 PM ET 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.

### [Ocala Oyster Fest](/events/ocala-oyster-fest-2026-04-18/) -- [Midtown Station](/directory/midtown-station/), free 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.

### [Let's Hang On (Frankie Valli Tribute)](/events/let-s-hang-on-frankie-valli-tribute-2026-04-18-14-30/) -- [Orange Blossom Opry](/directory/orange-blossom-opry/), $25 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.

### [Villages Cruise-In -- April](/events/villages-cruise-in-april-2026-04-18/) -- [Spanish Springs Town Square](/directory/spanish-springs-town-square/), free 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.

### [Renninger's Flea & Farmers Market](/events/renninger-s-flea-farmers-market-2026-04-18/) -- 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.

### [Dead Poets Society](/events/dead-poets-society-2026-04-18/) -- [Reilly Arts Center](/directory/reilly-arts-center/), $5 1959 New England boarding school, Mr. Keating, "O Captain! My Captain!" -- a movie night at the Reilly for $5. Bring tissues.

### [Shelly Belly Comedy: Live at the Marion Theatre](/events/shelly-belly-comedy-live-at-the-marion-theatre-2026-04-18/) -- [The Marion Theatre](/directory/the-marion-theatre/), $25-$35 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.

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## Sunday

### [Clermont Arts and Jazz Festival: Kim Scott & Keiko Matsui](/events/clermont-arts-and-jazz-festival-kim-scott-keiko-matsui-2026-04-19/) -- [Waterfront Park](/directory/waterfront-park/), $10 GA / $40 premium seating, 3-9 PM ET 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.

### [The Pirates of Penzance](/events/the-pirates-of-penzance-reilly-2026-04-19/) -- [Reilly Arts Center](/directory/reilly-arts-center/), $10-$58, 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.

### [Lost in Paradise: Tribute to Jimmy Buffett](/events/lost-in-paradise-tribute-to-jimmy-buffett-2026-04-19-19-00/) -- [Orange Blossom Opry](/directory/orange-blossom-opry/), $25, 7:00 PM ET Sunday night at the Opry, 7 PM, all Buffett. You know what you're getting.

### [Villagers Feud](/events/villagers-feud-eastport-town-square-2026-04-19/) -- [Eastport Town Square](/directory/eastport-town-square/), free "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.

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## The Full Lineup

Find all 65+ events this weekend at [villacalalineup.com/events/](/events/).

*Got a tip or event we should know about? Email [email protected]*