New Haven's grim reputation is long out of date. Located about halfway between Boston and New York, it's a great place to meet big city friends for a weekend. (They take Metro-North's New Haven line for $27 round trip; your round-trip Amtrak ticket from South Station is $98 or more, but it comes with ocean-side glimpses.) Stay cheap at the throwback Hotel Duncan (203-787-1273, from $44), and blow your cash on a show at the Yale Repertory Theatre (203-432-1234, www.yalerep.org) or the legendary try-out venue for Broadway hits, the Shubert Theater (888-736-2663, shubert.com). Wait in line for thin-crust New Haven-style pizza at Pepe's (203-865-5762) and finish up late at Louis' Lunch (203-562-5507), famed birthplace of the hamburger sandwich, where sozzled Yalies go until 2 a.m. Thursdays through Saturdays for a late-night snack. - Ann Silvio
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