Most people probably think of New Haven as an elite college town or the second-best place to eat some ’za on the East Coast. The Connecticut port is definitely both of those things, but there’s more to it than that! The Elm City is particularly nice to stroll during foliage season, so throw on your best flannel and pretend you’re a college kid for the day.
DO: Stroll Through Yale University
Go back to school, without all that pesky back-to-school anxiety, on a walk through this gorgeous campus. While you’re there, pop into the Beinecke Rare Book & Manuscript Library and the University Art Gallery for your cultural fix.
EAT: At “Food Truck Paradise”
Recent development has made the Long Wharf District one of the hottest dining destinations in New Haven, predominantly thanks to the 70-plus eclectic vendors that park along the waterfront most days of the week. Migrate to Ixtapa Mexican Tacos, La Chickymunchy, and Sandwiches El Cubano first for a taste of the best that the city has to offer.
ADMIRE: Locally Made Public Art
Take a DIY tour around town courtesy of ArtSites New Haven, which provides an interactive map of outdoor art throughout the city. Must-sees include international graffitists Hi Crew on Water Street, Alexander Calder’s sculpture work in Beinecke Plaza, and steelwork from Roy Lichtenstein on the Yale grounds.
SHOP: Vintage Rarities at Vintanthro
Upgrade your life with turn-of-the-century frocks, vintage decor, and other knickknacks at this curated boutique. 895 Whalley Avenue
EAT (AGAIN!): Charred Pies at Modern Apizza
New Haven is the promised land when it comes to the New England pizza scene, and this eight-decade-old pizzeria is the mecca. Just slightly off the beaten path from the city’s main pizza stretch, you’re guaranteed a shorter wait to savor specialty pies like its triple-meaty Italian Bomb. 874 State Street
HEAR: Experimental Tunage at Cafe Nine
Otherwise known around town as “the musician’s living room,” this long-standing venue takes its set list—and its craft tap selection—very seriously. You can’t predict what kind of performance you’ll stumble upon (acts range from ’70s ska and ’90s grunge to Tex-Mex keyboarding and surf rock), but at least you can prep for dirt-cheap happy hours. 250 State Street
SNACK: On Donut Crazy’s Creations on the Way Home
What better way to end your day than with big, bold, beautiful doughnuts? Grab a few rings before heading out of town; we recommend the apple cake for purists and the Fruity Pebbles–covered concoction for the young (and young at heart). 290 York Street