Every September, a few dozen golfers pull out of driveways in Saga Bay, Lakes by the Bay, and Cutler Ridge, load their clubs, and drive west and south toward Homestead. They're headed to the Cutler Bay Open Charity Golf Tournament, the town's marquee fundraiser and the one event most residents can name without checking a calendar. This year's edition lands on September 12, 2026, just under two weeks from now. In recent years it's been staged at Redland Golf & Country Club, out past the Cutler Bay town line entirely, in Homestead.
That's not a knock on the tournament. It's a useful fact, because it reframes what "local" actually means here. The event that carries Cutler Bay's name in its title happens somewhere else. The events that don't bother branding themselves, a Friday food truck night, a Saturday farmers market behind a church on Old Cutler Road, a golf cart parade down residential streets, are the ones that never leave town limits. If you want to feel the difference between Cutler Bay's civic identity and its daily texture, the fall calendar is where you'll find it.
A Fundraiser With No Home Course
Cutler Bay doesn't have its own golf course, so the Open has always had to borrow one. Back in 2019, the tournament was played at Miccosukee Golf & Country Club over in Kendall. By 2024 it had moved to Redland Golf & Country Club in Homestead, where it ran again in 2025, its two biggest fundraising years yet. The format hasn't changed much: an 18-hole four-person scramble, a shotgun start, a post-round lunch and raffle, and a hole-in-one contest sponsored by a local dealership. Land Rover South Dade backed the hole-in-one prize in 2025. Mercedes-Benz of Cutler Bay did the honors the year before.
The money stays local even when the golf course doesn't. The tournament exists to feed the Cutler Bay Community Fund, a town-run grant program for nonprofits working on education, beautification, and social services inside Cutler Bay. The 2024 tournament set a fundraising record, bringing in $17,260 for the fund, and Mayor Tim Meerbott used the moment to point out how much the event has grown year over year. In its earlier years, that fund helped support groups like Cutler Bay Middle School, Cutler Bay High School, the COAST Academy Parent Association, the EDGE Charitable Foundation, and the DEEP Foundation. The sponsor list reads like a directory of businesses that show up every year: Envirowaste Services Group, the Corradino Group, and Mercedes-Benz of Cutler Bay have all backed multiple editions, alongside neighborhood names like Sandbar Sports Grill, Macita's, Buffalo Wild Wings, and Miami Grill in Cutler Bay providing food and prizes along the way.
None of that requires a golf course inside town limits. It just requires a town willing to drive to one, then bring the money home.
The Market That Grew Past Its Own Parking Lot
If the golf tournament shows a Cutler Bay institution reaching outward for a venue, the Cornerstone Farmers Market shows the opposite: something that started here and is now exporting itself. The market runs Saturdays from 10 a.m. to 3 p.m. at Cornerstone Church, 20740 Old Cutler Road, with produce, honey, baked goods, jewelry, and small-batch skincare vendors, plus the occasional live set (School of Rock played the June 13 market this year). It's the kind of Saturday-morning fixture that shows up on a resident's weekly loop without much thought.
What's changed is the operator's footprint. The same team behind the Cutler Bay market has since launched a Thursday evening version, the Sunset Eats Night Market, at Palmetto Bay Park, and a monthly pop-up called Central Makers at the Gold Coast Railroad Museum near Zoo Miami. The original Saturday market on Old Cutler Road hasn't gone anywhere. But the fact that a market built inside Cutler Bay's church parking lot now runs weekly programming in two other communities says something about how thin the lines between these South Dade towns really are, at least for the people building the calendar.
The Nights That Never Leave Town
Contrast both of those with Food Truck Night, which happens at Cutler Ridge Park and nowhere else. The town's Parks and Recreation Department runs it roughly once a month, Fridays from 6 to 10 p.m., with a rotating lineup of trucks, live music, and kids' activities. One recent session ran April 4, 2025, and the town's own event listings show the same format repeating through the calendar year after year at Cutler Ridge Park, 10100 SW 200 Street, with lawn chairs and blankets welcome and sponsorship inquiries routed through the town's own Special Events office.
Two more fixtures round out the fall lineup, both entirely homegrown. The Hispanic Heritage Celebration is set for September 26, 2026, part of the town's annual events slate. Then on October 24, 2026, the Halloween Spooktacular & Golf Cart Parade takes over, pairing a kids' Halloween event with the golf cart processions that have become something of a Cutler Bay signature. The town repeats the format in December for its Holiday Celebration & Golf Cart Parade, which tells you this isn't a one-off gimmick but a recurring piece of how Cutler Bay marks its calendar.
Here's how the next ten weeks actually break down, and where each event really sits:
| Event | Date | Location | Inside Cutler Bay? |
|---|---|---|---|
| Cutler Bay Open Charity Golf Tournament | Sept. 12, 2026 | Redland Golf & Country Club, Homestead (recent years) | No |
| Hispanic Heritage Celebration | Sept. 26, 2026 | Town of Cutler Bay parks system | Yes |
| Food Truck Night | Recurring Fridays, roughly monthly | Cutler Ridge Park | Yes |
| Cornerstone Farmers Market | Saturdays, 10 a.m. to 3 p.m. | Cornerstone Church, Old Cutler Road | Yes |
| Halloween Spooktacular & Golf Cart Parade | Oct. 24, 2026 | Cutler Bay streets and parks | Yes |
Four out of five are entirely contained inside town limits. The one that isn't happens to be the one with Cutler Bay's name printed on the registration form.
What This Actually Tells You
None of this is a complaint about the golf tournament. Plenty of towns without their own course still manage to run a proud, well-attended charity event, and Cutler Bay's version has grown steadily enough to keep breaking its own fundraising record. But it's worth separating the branded civic event, the one built for visibility and sponsorship, from the unbranded ones that make up the actual rhythm of a week here. Nobody needs a marketing plan to explain why Food Truck Night draws a crowd to Cutler Ridge Park. It draws a crowd because it's close, it's free to attend, and it happens often enough that showing up becomes a habit rather than an occasion.
That distinction matters if you're trying to get a real read on a place. The big-name event tells you what a town wants to be known for. The recurring, low-key ones, a Friday truck line at Cutler Ridge Park, a Saturday table by the church on Old Cutler Road, tell you what a town actually is on an ordinary week. Both are worth knowing. Only one of them requires a drive to Homestead.
For more on what's shifting in Cutler Bay this year, including the Legacy Park and Municipal Complex project taking shape closer to Town Hall, see our rundown of what's changing around Cutler Bay in 2026. And if you want the fuller picture of the neighborhood itself, our Cutler Bay neighborhood guide is a good place to start.
If you're thinking about what it actually feels like to live day to day in Cutler Bay, or you're weighing this town against a few others in South Dade, Kelli Farrell has spent nearly three decades getting to know these streets, one Friday food truck line at a time. Let's Connect.
