Hipster Haven

The home of Yale is upping its game with arts, music and food


When it comes to Massachusetts’ interstate rivalries, “Harvard versus Yale” is to Ivy Leaguers what “Red Sox versus Yankees” is to sports fans. In both cases, of course, we root-root-root for the home team.

That said, props when due: Yale’s city of New Haven, where you’ll still find some urban grit in the seams of those tweed jackets, is increasingly competitive with upmarket Cambridge in terms of preserving hipster-skewing college-town charm. Make no mistake; we’re still loyal to the People’s Republic. But it’s worth taking a crash course on visiting Connecticut’s second-largest city.

Start at the Study at Yale, part of Study Hotels, a brand siting smart, sophisticated properties at East Coast campuses. The 124-room hotel has sumptuous leather seats with academia-inspired accents, like signature seersucker robes, and elegant farm-to-table restaurant Heirloom.

Wake up with java from Koffee?, a curious little gourmet coffee house that’ll kick off your morning with a Nutella latte or, after 5 pm, pour hot and cold coffee- and tea-based cocktails.

Bar-wise, you’ll also want to blow by Three Sheets, a “friendly neighborhood gastrodive” popular with indie-punk crowds. Gobble neat eats like octopus banh mi at patio picnic tables and sip craft beers like Hull’s Export Lager, a beloved local brew that was revived in limited quantities this year after a four-decade hiatus. If you’re not game for its pool table backroom—which also hosts monthly second-Saturday art shows—hit up boisterous Barcade to down brews and drop coins in dozens of blinking nostalgia-invoking machines like four-player Pac-Man. But save some quarters for the fun, cheap scene at 168 York Street Cafe, a gay bar tucked in the lower level of an unassuming historic brownstone. It’s home to boozy brunches on a cloistered rear patio and drag shows with some of New England’s quirkiest queens.

There’s actually an alternative edge to much of the arts and culture scene in New Haven. Take basement-level venue Yale Cabaret, currently celebrating 50 years of boundary-pushing works like For Your Eyes Only, a recent show exploring the webcam sex industry and fetish culture. Artspace, a Civil War-era furniture factory-turned-nonprofit gallery complex, exhibits experimental work and is a key player in cultural events like the City-Wide Open Studios series. And Lyric Hall, a recently restored former opera and vaudeville theater, is stuffed with antique objets d’art and a lineup of everything from burlesque shows to adult puppetry.

Before curtain call, stop into Strange Ways across the street, the New Haven storefront of a popular online shop specializing in unique gifts—particularly pins, patches and other funky flair (including exclusive collections launched with cult movie stars) that’ll dress up your denim jacket. For more geek-chic glam, visit Fashionista Vintage & Variety to raid a righteously retro, gently used wardrobe.

Rock your new threads at one of the city’s live music halls like Toad’s Place, a legendary Yale-side spot with a storied history—Bob Dylan once played a career-long, nearly five-hour concert here—that earned it a spot on Rolling Stone’s list of America’s best big-room venues. Cocktail bar Firehouse 12, located inside a renovated firehouse, has an on-site recording studio that performs double-duty as a 75-seat auditorium for jazz concerts and more. And Cafe Nine—dubbed “the musician’s living room” for its intimate, lo-fi style—is where to catch buzz-building bands on their way to breakout status.

Photo credit: Elizabeth Grant

As dining headliners go, you could stick to historic favorites like Louis’ Lunch, which the Library of Congress recognizes as the 1895 birthplace of the hamburger sandwich served on white toast, or the first location of Frank Pepe pizzeria, originator of coal-fired New Haven-style pies. But the city is also earning a reputation for one of New England’s best contemporary dining scenes thanks to options like Zinc, a stylish, on-trend eatery with electic global cuisine and an outstanding wine list, and Barracuda Bistro & Bar, a Latin-American affair for seafood paella, Peruvian chicken and refreshing rum cocktails.

On your way out of town, stop into the Pez Visitor Center, a 4,000-square-foot manufacturing facility and museum dedicated to the candy and its famous collectible dispensers. It’s a fun final stop—because really, every hipster-friendly road trip requires an ironic ending. 

Traveler’s Check

  • – For a truly bizarre detour, check out the Cushing Brain Collection at Yale, a small museum of 400 preserved brains in softly glowing jars, plus rare manuscripts and historic neurological artifacts.

168 York Street Cafe yorkstreetcafe.com; ArtSpace artspacenewhaven.org; Barcade barcadenewhaven.com; Barracuda Bistro & Bar (203-691-5696); Café Nine cafenine.com; Fashionista Vintage & Variety fashionista-vintage-variety.com; Firehouse 12 firehouse12.com; Frank Pepe Pizzeria Napoletana pepespizzeria.com; Koffee? koffeefamily.com; Louis’s Lunch (203-562-5507); Lyric Hall lyricalhallnewhaven.com; Pez Visitor Center us.pez.com; Strange Ways strange-ways.com; The Study at Yale studyatyale.com; Three Sheets threesheetsnh.com; Toad’s Place toadsplace.com; Yale Cabaret cab50.org; Zinc zincfood.com

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