This joke never falls flat: When it comes to the tastiest Boston challah, here’s all the information you knead to know. Reminder to always confirm pickup and delivery dates before spending your dough at these favorites!
Bakey
It’s no secret that we at JewishBoston love the fresh-baked, aromatic, kosher treats at Bakey, with locations in Boston, Brookline, Newton and Kendall Square. (Check out our full ordering guide.) They offer a full Rosh Hashanah menu at all locations, for pickup from Sept. 21-24.
Blacker’s Bakeshop
A great choice for allergy-sensitive diners, Blacker’s is nut-free (and kosher). They offer round Rosh Hashanah challah—plain, egg-free, chocolate chip and more—by pre-order or first-come, first-served walkup; pre-order pickups happen Sept. 19-20, with extended hours Sept. 21-22 if you didn’t plan ahead.
The Butcherie
A challah mainstay since 1972, this Brookline kosher destination serves rolls, rounds and dough to bake at home—and check out their in-store Rosh Hashanah specials, from meats to wines, lasting through Sept. 22.
Cheryl-Anns’ of Brookline
The legendary Brookline kosher bakery made a comeback in 2024 after a three-year closure due to a fire. They’re known for exceptional braided, pan and round challah, in many flavors (plain, sesame, poppy, raisin and whole wheat). Can’t make it to their Chestnut Hill flagship? You can find their products at Roche Bros., Sudbury Farms and Shaw’s.
Clear Flour Bread
Plain, raisin or sesame: Clear Flour’s challah (not kosher), available after 10 a.m. on Fridays, has an earthy, dense texture. They don’t take pre-orders; they’re baked fresh and available on a first-come, first-served basis, alongside longtime staples like pizza dough. For Rosh Hashanah, they’ll offer plain or golden raisin challah in a holiday round, available from Friday, Sept. 19, at 9:15 a.m.
Fornax Bread Company
This Roslindale bakeshop (named after the Roman goddess of ovens!) has lines out the door thanks to their globe-trotting bread menu, from baguettes to boules to Irish soda bread (not kosher). Those in the know visit Thursday through Saturday to stock up on their super-buttery challah, baked fresh and available while supplies last.
Hi-Rise Bread Company
The quintessential, character-filled Huron Village bakery (not kosher)—luring everyone from Harvard profs to stroller-wrangling families since 1996—offers raisin challah made laced with wildflower honey, as well as plain versions, for pre-order. But that’s not all: On non-holiday visits, you’ll find a kids’ menu stocked with challah sandwiches aplenty: Nutella and powdered sugar, peanut butter and jam, grilled cheese and even hot dogs on challah buns.
Inna’s Kitchen
Your Newton go-to for nut-free, gluten-free, dairy-free, kosher, pre-prepped sweets and savories, including an assortment of frozen challah, available fresh on Fridays. Note: They’re closed on Saturdays.
Mamaleh’s
The classic yet modern deli (not kosher) in Boston, Brookline, Cambridge and now Somerville traditionally serves classic round and raisin challah ($10) as part of an extensive Rosh Hashanah menu, with all the signatures: noodle kugel, brisket, potato latkes and lots more. They also serve vegan challah ($12).
Mandylicious
Sharon baker Mandy Silverman is renowned for unusual, kosher challah flavors: cookie dough, peanut butter cookie, caramelized onion, spiced oat-baked apple and more. In a DIY mood? She posts baking tips on her active Instagram page, and she also hosts classes. And if you’re feeling really creative, try to attempt her new upside-down challah pizza.
Rosenfeld’s Bagels
A kosher mainstay in Newton Centre since 1973, Rosenfeld’s is mainly known for bagels—although people also rave about their challah, which comes in raisin, onion, whole grain, sesame, poppy or chocolate. Expecting a crowd? Get their celebration challah, weighing a healthy three pounds—available in custom shapes.