Where to Get Great Hamantaschen in NYC

[Photograph: Shutterstock. All others Aly Miller unless otherwise noted]
You've probably noticed them in the bakery, and possibly given them a try—the triangular, filled cookies with the pinched corners. But what are hamantaschen?
The first hamantaschen appeared on record in 16th century Germany. The poppy-seed filled cookies were aptly named Mohntaschen, which is German for poppy seed pockets. When Jews left Germany for Eastern Europe, they brought the pastries with them, adding a Hebrew prefix, the definite article "ha." The cookies further evolved in Czechoslovakia and Bohemia, where fillings of prune and other dried fruits were added by the 17th century.
The way we spell hamantaschen today is characterized not by the seeds that fill them but by Haman, the biblical villain who plotted, unsuccessfully, to kill the Jewish people of Persia. Poppy seed pockets were baked to celebrate Purim, a Jewish holiday commemorating their deliverance from Haman with dancing, drinking, and of course, Hamantaschen.
Baked into these triangular cookies are more than just poppy seeds, prunes, and apricots, but stories of etymology, migration, triumph, fashion choices (apparently Haman wore a three-cornered hat), and Mardi Gras-like revelry. In New York, Hamantaschen are baked year-round and it seems that everyone from Hungarians to Italians has a recipe. We wanted to find the best. What better time to set out than the week leading up to Purim?
Tasting our way from the Upper West Side to the Lower East Side, and from Williamsburg to Midwood, Brooklyn, we became critics of dough, fillings, ratios of dough to filling, and bakeries. We believe that the ideal hamantaschen should, above all, taste of their slow-cooked fillings. That usually means a high filling to dough ratio, and definitely means a filling made with quality dried fruit, seeds, or chocolate. The dough should resemble soft, pastry-like cookies rather than hard, dry shortbread ones; and we prefer three-bite-sized cookies to ones the size of hockey pucks. Here are our favorites in NYC.

Manhattan

The Hungarian Pastry Shop
Varieties: walnut, prune
Price: $2.35 for a large cookie
The bakery that started this expedition is across from the Cathedral of St. John the Divine on Manhattan's Upper West Side. It offers a cozy atmosphere that tempts us to curl up with a book, some tea, and an endless supply of their satisfying hamantaschen.
Pros: The cookie itself had very enjoyable citrus notes as well as a dash of cornmeal that lends an pleasing textural bite. This bakery offered the only walnut variety on our quest, and we loved it.
Cons: The prune filling was too sparse in proportion to the cookie. Overall a very dense experience.

Russ & Daughters

Varieties: apricot, poppy
Price: $1.27 each, 14.99/lb for small cookies
This classic appetizing store on Manhattan's Lower East Side was bustling during the lunch hour, but service was quick and we found the hamantaschen to be right on par with the quality of their popular bagels with lox.
Pros: The thin, pie crust-like cookie had enjoyable notes of almond and a slight tang from the addition of cream cheese (an ingredient that's often used in traditional recipes). The filling in each variety had deep, authentic fruit flavors that were likely made from the colorful display of dried fruits in their front window. The apricot flavor, recommended to us by the counter attendant, quickly became an overall favorite.
Con: The cookie-to-filling ratio was perfect at 1 to 1, but the cookie itself was far too small!

Moishe's Bake Shop

We definitely felt a need to visit Moishe's as it is perhaps New York's most well-known kosher bakery.
Varieties: prune, poppy
Price: $1 for a small cookie
Pros: We loved that small and large sizes of each flavor are available.
Cons: We found the filling, however, to be overcooked and artificially flavored. The cookie was overly crumbly and we put Moishe's towards the bottom of our favorites list.

William Greenberg Desserts

This Upper West Side bakery sells a decent rugelach and some of our favorite chocolate babka, so we wondered how they'd handle hamantaschen.
Varieties: poppy, cheese
Price: $3.50 for a large cookie
Pros: This distinctly butter cookie reminded us of a Nilla wafer. The smooth, shiny appearance of the cookie and the mountain of filling exuding out their tops made these guys the nicest looking, overall. The poppy filling resembled a spread, favorable to some of the globbier fillings, and the only cheese variety we found was dense, sweet, but surprisingly enjoyable.
Con: A slightly dense experience.

Zabar's

This iconic gourmet food store has one of the best cheese, appetizing and cured fish dept's in NYC.
Varieties: prune, apricot
Price: $4.00 for a large cookie
Pros: This cookie met all our expectations for a hamantasch. The fillings were bright and jelly-like, and the crust erred on the side of pie crust rather than a cookie. They looked very cute on their plate in the bakery case.
Cons: In the end, though, they didn't blow us out of the water, which made them not quite worth their price tag (which was the highest we encountered).

Orwasher's Bakery

This over 90 year old bakery is mainly known for its breads, but does sell a selection of pastries and cookies.
Varieties: apricot, raspberry
Price: $0.44 each
Pros: The 1 to 1 cookie-to-filling ratio was a good start for these miniature cookies. The counter attendant informed us the tart-like crust had cream cheese in it, which we thought gave it a nice bite. The pinched corners gave the cookies a rustic feel.
Cons: Thought the fruit filling was deeply flavored, much of it had boiled out of the center, leaving it disappointingly hollow.

Breads Bakery

[Photograph: Robyn Lee]
This Israeli bakery in Union Square makes some of our favorite babka (and breads, period) so it was no big surprise that they ruled in the cookie department as well.
Varieties: apple, poppy seed, chocolate, vanilla and chocolate chip, marzipan
Prices: $2 each, 2 for $3.95, 6 for $9.95
Pros: The hamentaschen at Breads Bakery come with a thin, snappy cookie that's lightly buttery and crumbly. The fillings are mostly non-traditional: apple that's a lot like apple pie, chocolate brownie goo, vanilla and chocolate chip, and sweet marzipan, though there's also a great poppy seed filling for those who'd prefer to kick it old school.
Cons: None to speak of.

Brooklyn

Sander's Kosher Bakery

Our Brooklyn search began on Lee Avenue in Williamsburg, the bustling Main Street to several thousand Hasidic families. Purim festivities had not yet begun but this bakery was stocked, notably, with blueberry and chocolate Hamantaschen.
Varieties: Prune, apricot, chocolate, raspberry, blueberry
Price: $0.50 each
Pros: What these cookies lack in form they make up for in filling, especially the soft, just-sweet-enough prune-filled cookie. If you're on your way to a large Purim party, this is the place to go in terms of price and variety.
Cons: The milk chocolate filling, spread thick like a ganache, tasted commercial but enjoyable, and the blueberry filling was bold, although too artificially sweet for our tastebuds.

Gombo's Heimishe Bakery

A short walk down Eastern Parkway from the Brooklyn Museum led us to Gombo's, a Kosher bakery in Crown Heights. It's unmistakably hamantaschen time here, with boxes and trays of cookies for every flavor craving.
Varieties: chocolate, apricot, raspberry, poppyseed
Price: $7.99/ lb for small cookies
Pros: Whether the soundtrack of Israeli party songs—audible both inside and outside of the store—was for Purim pre-gaming or not, the music definitely added to Gombo's festive ambiance. What makes their crowd-pleasing, too-sweet Hamantaschen unique is the floral almond flavor that you can taste in the cookie. The chocolate ganache filling was the best.
Cons: Like Sanders, their fillings were closer to jelly than to fruit itself. The poppyseed filling formed an unfortunate, solid glue.

Isaac's Bake Shop

Isaac's Bake Shop (which is across the street from Ostravitsky's, whose hamantaschen unfortunately didn't stack up), was less flashy than any other Kosher bakery we visited. It's as close to old school as we got.
Varieties: chocolate, prune, raspberry, apricot
Price: $1.77/5
Pros: The Hamantaschen were tasty enough to speak for themselves, especially the chocolate and poppyseed varieties. The chocolate Hamantasch, dipped in dark chocolate, has a filling less milk-chocolaty than the other chocolate contenders, resembling more of a gooey babka filling than Nutella. The poppy filling was less congealed than the others, boasting the true, almost-bitter flavor of seeds. The crust resembles buttery shortbread with a hint of salt. Go there for the old-style vibes, and ask if Isaac is around to help you.
Cons: Isaac's looks like the kind of place where you'd expect to hear Yiddish, but if that's what you're aiming for, try visiting when it's busy. On a quiet weekday afternoon, we were helped by someone who didn't have much in terms of authenticity to offer.

Queens

La Guli Pastry Shop

Our only Queens contender came from an Italian bakery best known for its cannoli and gelato.
Varieties: prune, raspberry
Price: $2.00 each
Pros: The edges of these cookies were delightfully scalloped, revealing a large dollop of fruity filling in the middle. And they didn't cut any corners in terms of filling, either: you could taste the crunch of raspberry seeds in almost every bite, and the prune was as close to dried plums as you can get. If you want an Italian Hamantaschen experience, La Guli might be the only place to get it.
Cons: This bright yellow, light and crispy cookie was perhaps the least traditional Hamantasch.