The Early Arrival
Mid-May warmth has coaxed the first heirloom tomatoes out of Hudson Valley and Long Island greenhouses nearly ten days ahead of the usual Memorial Day debut. By May 19, three farms have already set up crates of Cherokee Purples, Early Girls, and a handful of Brandywines at Union Square Greenmarket, with Grand Army Plaza and McCarren Park following close behind. These aren't the August behemoths—expect tennis-ball sizes, thinner skins, and a sharper acidity that works beautifully with fresh mozzarella and sea salt.
The rush starts around 8:45 a.m. at Union Square, where regulars know that heirlooms vanish by 10 a.m. on Wednesdays and Saturdays. Stall positioning matters: the north end of the market along 17th Street hosts two farms with early-season stock, while the southern rows near 14th Street lean toward greens and rhubarb for another week. Timing and geography separate the casual shopper from the home cook who plans dinner around a single perfect tomato.
Union Square Greenmarket: The Wednesday and Saturday Sprint
Eckerton Hill Farm out of Lenhartsville, Pennsylvania, occupies the northwest corner near the playground fence and typically brings 40 to 50 pounds of mixed heirlooms on Wednesday mornings. Their Early Girls are small, firm, and ideal for slicing thin; by 9:30 a.m., only the bruised seconds remain. On Saturdays, Stokes Farm from Old Tappan, New Jersey, sets up two stalls east of the pavilion with a rotating selection that this week includes Black Krims and a few experimental varieties the farmer refuses to name until the fruit proves itself.
Both farms price early heirlooms between six and eight dollars per pound, a premium justified by the greenhouse heat required to hit this narrow window. Cash moves faster than card readers when a line forms, and it will form. Arrive by 8:50 a.m., scan the crates for splits or soft shoulders, and be prepared to take whatever looks best rather than hunting for a specific cultivar. The selection will triple by mid-June, but these late-May pioneers carry a distinct thrill.
Grand Army Plaza: Brooklyn's Saturday Morning Ritual
Grand Army Plaza Greenmarket operates Saturdays only, and the heirloom situation is more relaxed than Union Square's scrum. Evolutionary Organics, a farm based in New Paltz, anchors the plaza's eastern flank near the entrance arch and brought its first heirlooms on May 17. Expect smaller crowds here until 10 a.m., though by 11 a.m. the best fruit is gone. The farmers are chattier, willing to discuss soil amendments and varietal quirks while bagging your tomatoes in recycled paper.
Two other stalls worth checking: Rogowski Farm from Pine Island occasionally carries greenhouse tomatoes but focuses on spring lettuce and peas through May, while Paffenroth Gardens from Warwick brings a limited heirloom selection starting the last Saturday of the month. The plaza's open layout and proximity to Prospect Park make it easy to combine a market run with a morning walk, provided you hit the tomato stalls first. Once they're gone, no amount of optimism will restock them.
McCarren Park: Williamsburg's Sunday Window
McCarren Park Greenmarket runs Sundays from 8 a.m. to 3 p.m., though the heirloom window closes much earlier. Bobolink Dairy and Bakehouse from Vernon, New Jersey, parks near the Bedford Avenue gate and supplements its cheese and bread with a modest tomato selection sourced from a partner farm. The quality is excellent, the quantity limited—plan on 20 pounds total, split between three or four varieties, all sold by 9:15 a.m.
This market draws a younger, brunch-adjacent crowd that tends to prioritize prepared foods and flowers over produce, which works in favor of the early riser. By 10 a.m., the tomato crates are empty but the line for sourdough stretches ten deep. If you live in Williamsburg or Greenpoint, McCarren offers the most convenient heirloom access without the Union Square intensity, provided you treat the 8 a.m. opening as a firm appointment rather than a suggestion.
What to Look For and What to Skip
Late-May heirlooms differ from their July and August counterparts in size, flavor concentration, and shelf life. Look for tomatoes with taut, glossy skin and a slight give near the stem—too firm means they were picked early and won't ripen properly at home, too soft means they'll collapse by tomorrow. Color should be deep and even; pale shoulders indicate uneven ripening and a mealy texture. Cherokee Purples and Black Krims show more color variation than red varieties, so judge by feel rather than appearance alone.
Skip any tomato with visible splits, which invite rot, and avoid the temptation to refrigerate. Early-season heirlooms have thinner cell walls and suffer more texture damage from cold storage than their thick-skinned summer siblings. Keep them stem-side down on a countertop, away from direct sunlight, and plan to use them within two to three days. The flavor is bright and acidic now; by late June, the same varieties will taste sweeter and more complex as soil temperatures and sunlight hours increase.
Practical Notes for the 9 a.m. Visitor
Securing early heirlooms requires a small shift in weekend routine. Most stalls accept card payments, but cash eliminates the wait while a farmer fumbles with a Square reader. Bring your own bag—paper or cloth—since many farms charge for bags or simply run out. Dress for standing and walking; Union Square's pavement is unforgiving, and Grand Army Plaza offers little shade before 10 a.m.
- Union Square Greenmarket: Wednesdays and Saturdays, 8 a.m. to 6 p.m.; heirlooms gone by 10 a.m.
- Grand Army Plaza Greenmarket: Saturdays, 8 a.m. to 4 p.m.; heirlooms available until 11 a.m.
- McCarren Park Greenmarket: Sundays, 8 a.m. to 3 p.m.; heirlooms sold out by 9:15 a.m.
- Expect to pay $6 to $8 per pound for early-season heirlooms across all three markets
- Peak selection occurs in the first 90 minutes after opening; plan accordingly
Why Late May Matters
The late-May heirloom window lasts only two to three weeks before the main-season harvest begins and prices drop. Early tomatoes command a premium not just for their scarcity but for their distinct flavor profile—sharper, more mineral, less sugar—that pairs exceptionally well with spring produce still lingering at market stalls. Asparagus, snap peas, and the last of the spring onions all share a crispness that balances the tomato's acidity in ways that feel mismatched once summer squash and corn arrive.
This is also the moment when farmers test new varieties and greenhouse techniques, making the selection more experimental and less predictable than the August standard. A tomato that appears in late May may never return, replaced by a more reliable or higher-yielding cultivar. For the cook who values novelty and the fleeting nature of seasonal ingredients, these few weeks offer a chance to taste something that won't repeat, at least not in the same form or from the same soil.
Sources consulted: GrowNYC Greenmarket · NYC Parks · Brooklyn Borough Information · New York State Department of Agriculture · MTA Trip Planner
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