By 9 AM on a Saturday, the parking lot behind Memorial Plaza has already turned into something else. Coolers are stacked two high next to folding tables. A pickup with Dutchess County plates backs into its usual spot. Kyle Nisonger, who drives forty miles down from Maple View Farm in Poughquag every week, sets out whatever the no-till fields gave up this month. A few tables over, Nicole Carangelo of Letterbox Farm in Hudson, ninety miles north, unloads pastured poultry and bone broth she started making because farmers markets like this one are one of the only places that let a small producer sell direct, year-round, without a middleman.
This is the Pleasantville Farmers Market, and it runs every Saturday of the year, rain or shine, from 8:30 AM to 1 PM in the warmer months and a shorter 9:30 to noon window from January through March. It is the largest year-round farmers market in Westchester County, and it has been voted "Best of Westchester" eleven years running. None of that is new information if you already shop there. What's easy to miss, even for regulars, is what else is scheduled for that exact same patch of pavement later this year.
The Calendar Nobody Prints Together
The market and the Village's Concert Series are two separate programs run by two different parts of Pleasantville's civic life, and they don't usually get mentioned in the same sentence. But they share an address. Both happen at Memorial Plaza. Two of this year's five concert nights have already come and gone. The three still ahead, August 22, September 26, and October 24, all land on Saturdays when the market has already been open since morning.
| Date | Farmers Market (8:30 AM–1 PM) | Concert Series (7–9 PM) |
|---|---|---|
| August 22 | Open | SOUL Brewing Company on site |
| September 26 | Open | SOUL Brewing Company on site |
| October 24 | Open | SOUL Brewing Company on site |
Out of fifty-two Saturdays the market runs each year, only five get a concert added on top, and this year all three remaining ones fall on days when the market has already drawn its regular Saturday crowd that morning. If you're the kind of household that treats the market run as a fixed weekly habit, that means three more Saturdays this year where the same trip that starts with produce and eggs can end, twelve hours later, back in the same spot with music and a beer from a local brewery.
What Actually Happens After the Market Packs Up
The market clears out by early afternoon. Vendors fold their tables, the trucks pull out, and Memorial Plaza sits quiet for a few hours. Then, on those five concert Saturdays, it opens back up as something closer to a Village-run block party. The Concert Series is a Village of Pleasantville production, held right at the Memorial Plaza Civic Space, with SOUL Brewing Company providing food and drinks for each of the five evenings on the 2026 calendar: June 27, July 25, August 22, September 26, and October 24, all running 7 to 9 PM.
It's a small program by design. No ticket, no gate, just a local brewery and a stage in the same plaza where the market sets up every week. That modesty is part of what makes it durable. It doesn't need to sell out to happen again next year.
The Bigger Show That's Having a Harder Year
Contrast that with the Pleasantville Music Fest, the town's larger, ticketed music event, which local news outlet The Examiner reported this year lost $150,000, a loss significant enough that the paper's own coverage raised real questions about whether the festival continues in its current form. The Concert Series and the Music Fest are different events with different scales and different funding models, but the gap between them is worth knowing if you've assumed all of Pleasantville's outdoor music runs the same way. One is underwritten by a modest Village budget and a local brewery pouring drinks. The other depends on ticket revenue covering a much bigger production, and this year it didn't.
None of this changes your Saturday plans. But it's the kind of detail that explains why the small, unglamorous market-plus-concert combination at Memorial Plaza keeps showing up on the calendar year after year while the flashier festival is publicly wrestling with its future.
Dinner Without Leaving the Plaza
If you're staying through a concert night, or just don't feel like cooking after a market haul, you don't have to go far. Wonder, the multi-restaurant food hall concept that plates dishes attributed to chefs including Bobby Flay, José Andrés, and Marcus Samuelsson, operates out of 70 Memorial Plaza, the same complex as the market and the concert stage. It's a delivery-first operation, but pickup and limited dine-in are available too, which makes it a workable option on a night when you're already parked at the plaza and don't want to move the car.
A short walk from the plaza gets you to a handful of longer-running options: Chatterbox Restaurant & Bar for Italian-American with a modern edge, Vela Kitchen for contemporary American a block from the Metro-North station, The Raconteur Bar & Kitchen for small plates and cocktails, and Southern Table for farm-driven Southern comfort food. On a non-concert Saturday, the same short walk gets you to the Jacob Burns Film Center, the nonprofit art house cinema housed in the restored 1925 Rome Theater on Manville Road, which programs new releases alongside documentaries, 35mm screenings, and filmmaker conversations, and which the New York Times has credited with helping revive Pleasantville's downtown in the first place.
After October 24
Once the last concert wraps in late October, the market doesn't stop. It keeps running every Saturday through the fall, past the point when the evenings get too cold for an outdoor stage, until the Saturday before Thanksgiving. At that point the whole operation moves indoors to Pleasantville Middle School, where it continues through the winter months before returning outside to Memorial Plaza in the spring. So the plaza's calendar this year isn't really two separate schedules, a market and a concert series that happen to overlap. It's one continuous rhythm that changes shape with the season: outdoor and musical through October, quieter and indoor through the winter, back outside when the weather turns again.
If you've been treating the Saturday market as a habit and the concert series as a separate, occasional thing to check for, this year's calendar makes the case for treating them as one plan. August 22 is the next one. Mark it, and bring an appetite for both halves of the day.
For more of these week-by-week reads on what's actually happening around Northern Westchester, from Pleasantville to Chappaqua to Bedford, Harriet Libov covers the towns she's lived in and around for decades through neighborhood guides and a regular podcast. Let's Connect if you'd like these delivered directly.
