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What: Like other Northeast cities that have seen large settlements of Italian immigrants (see Boston, Philadelphia), New Haven has a pronounced soft spot for Italian pastries and cookies. A multitude of cannoli, sfogliatelle, zeppole, and their ilk, plus a host of colorful cookies—sugar, almond, amaretto, cherry butter, milanos, star and acorn and snowball cookies—are joined by a brisk summertime Italian-ice business at the city’s beloved historic pastry shops.
Where: Founded in 1922, Libby’s Italian Pastry Shop (139 Wooster St., map) has the old-fashioned wrought-iron décor to match its old-fashioned cookie and pastry display, proudly tended to by the handful of little Italian-American ladies behind the counter. This storied place has a fortunate location a block from Pepe’s and across from Tony & Lucille’s, making it an ideal post-pizza (or -calzone) sweet spot. Even better: Its refreshing Italian ices are available year-round.
When: Mon, 11:30am-9pm; Wed & Thurs, 11:30am-10pm; Fri & Sat, 11:30am-11pm; Sun, noon-9pm
Order: It’s hard to choose, but we recommend a cannoli (about $2, depending on kind) and a lemon ice (from $1.75), the most popular of ices here. Cannoli are available in many, many flavors—from cappuccino to pistachio to peanut butter—but we are suckers for the plain creamy ricotta and chocolate cream (get the mezze-mezze to try half and half of each).
Alternatively: Another popular, historic (est. 1929), family-owned Italian-pastry purveyor is Lucibello’s (935 Grand Ave., map)—not on the Little Italy strip of Wooster Street, but just a few blocks north.
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