When does the Pineapple Festival start this year? It's a fair question if you've lived in Jensen Beach long enough to remember when the answer was always the same weekend in November. It hasn't had an answer since 2019.
The festival that put Jensen Beach on a lot of people's calendars for three decades, arts and crafts booths, a Bahamian market with a Junkanoo parade, national touring acts, midway rides, ran its last event on the weekend of November 22 through 24, 2019, its 32nd consecutive year. It never came back in 2020, 2021, or any year since. What has come back, and what's opened a short drive from it on Hutchinson Island itself, tells you more about how the neighborhood actually spends a Saturday now than the old festival's absence does.
Why the Chamber Let It Go
The Jensen Beach Chamber of Commerce produced the Pineapple Festival from its start, launched in 1988 alongside the town's centennial celebration and headlined that first year by a concert from Marie Osmond. In its bigger years the festival drew an estimated 50,000 people to Jensen Beach Boulevard over a single weekend, and the chamber has put cumulative attendance since 1988 at roughly a million. By its final run in 2019, the crowd the chamber was managing had settled closer to an estimated 15,000, a meaningful step down from the festival's peak, in an area that was already tight on parking and traffic for one weekend a year.
Ron Rose, the chamber's president and CEO, was direct about why it didn't return when a reporter asked him about it two years later.
"It's not going to happen this year, obviously."
Rose pointed to two practical problems: top-tier entertainment isn't cheap, and admission had always been free, so the festival leaned on sponsorships to cover costs that kept climbing. He also noted that many of the downtown businesses that used to rally around the event had changed hands over the years, and the newer owners didn't carry the same enthusiasm for underwriting a street festival that closes their block for a weekend. Neither the chamber nor the county has announced plans to revive it in its old form.
What Filled the Gap
What the chamber did instead was smaller, cheaper to run, and built around a different kind of participation. In June 2025 it launched the first annual Jensen Beach "Everything Pineapple" Tasting Tour, timed to International Pineapple Day, sold as a $35 tasting passport rather than a free three-day event. The first year's tour routed ticket holders through roughly 30 restaurants across a footprint wider than the old festival ever covered: Jensen Beach, Rio, Sewall's Point's Harbour Bay Plaza, and Hutchinson Island.
The second annual tour ran this past summer, on Saturday, June 27, starting at 3 p.m. That it happened again mattered more than it might sound. A one-off food event is easy to run once and quietly drop. A second year means the chamber found enough participating restaurants and enough passport buyers to justify doing it again, which is a different kind of proof than a press release promising it'll return.
Here's how the two events actually compare, side by side:
| Pineapple Festival (1988–2019) | Everything Pineapple Tasting Tour (2025– ) | |
|---|---|---|
| Format | Three-day street festival: concerts, midway rides, arts and crafts | Single afternoon, restaurant-to-restaurant tasting passport |
| Footprint | Jensen Beach Boulevard, downtown only | Jensen Beach, Rio, Sewall's Point's Harbour Bay Plaza, Hutchinson Island |
| Cost to attend | Free admission, paid tickets for premium concerts | $35 tasting passport |
| Producer | Jensen Beach Chamber of Commerce | Jensen Beach Chamber of Commerce |
| Peak reach | Estimated 50,000 in a single weekend at its height | Two years running, most recently this June |
The tasting tour isn't trying to be the old festival at a smaller scale. It's a different product built by the same organization, one that doesn't require closing a boulevard or booking a national act, and one that happens to reach onto Hutchinson Island in a way the downtown-only festival never did.
Downtown's other standing fixture hasn't gone anywhere in the meantime. Jammin' Jensen still runs every Thursday evening, its own long-running mini-festival of local art and music, and residents who track that calendar already know it hasn't skipped a beat.
The Island's Own New Fixture
The more consequential change for anyone living on Hutchinson Island itself happened at 4304 NE Ocean Boulevard, the site of the former Gin Mill Bar and Grill. WPTV described the building as largely dormant for years before renovation crews moved in to gut it for RockHouse Live Grille & Venue, a music-forward restaurant and bar chain adding a new location there. The venue opened in January 2026, following renovations that reportedly began the previous July and removed nine tons of debris at a cost approaching $1 million.
Emilio Torres, who heads the venue's VIP Rock Room and retail operation, described the scope of the rebuild plainly.
"The bones were here, we've pretty much gutted it out."
What opened is built around a 50-foot bar that Torres says is the longest in Jensen Beach, an indoor main stage, and a second outdoor stage built where the site's old tiki bar used to sit. It's a full restaurant and bar as much as a concert room, and it hired locally for front-of-house and kitchen positions ahead of its January opening.
The detail that matters most if you live nearby isn't the size of the bar. It's the shuttle. RockHouse Live runs a bus connecting the venue to downtown Jensen Beach, which means a night that starts on the island doesn't have to end there, and a night that starts downtown at Jammin' Jensen doesn't require choosing between the two. That's a genuinely new option on a stretch of the island that has been the subject of its own north-south divide before, where the causeway end draws most of the attention and the quieter south end, where Island Club sits, has run on its own routine.
One Causeway, Fewer Choices to Make
None of this replaces the Pineapple Festival's scale, and nobody at the chamber has suggested it's trying to. What it adds up to is a calendar with more entry points than it had a year ago: a Thursday tradition that never stopped, a summer tasting tour that has now run two years in a row and reaches further than the old festival did, and a new venue on the island itself with a shuttle that makes the causeway a shorter trip than it used to feel like.
If you're weighing whether that shift changes anything about life on this part of Hutchinson Island, from the Island Club neighborhood south of the causeway to the newer activity clustering near it, that's a conversation worth having with someone who tracks these changes as they happen, not after the fact.
Janyne Kenworthy has spent decades following exactly this kind of shift on Vero Beach's barrier islands and can walk you through what it means for a specific address. Let's connect.
