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See: Hard to believe that bustling New Haven, with its innovative arts vibe, Yale University liveliness, and red-hot culinary scene was founded by Puritans in 1638. A shady green heart beats at the center of it all: historic New Haven Green is a 16-acre oasis that’s been there since the city’s start, not far from the Old Campus’s dizzying turrets and towers.
The green is edged by Chapel Street, a main thoroughfare where everything happens, including free entry to the outstanding Yale University Art Gallery – from early African art to late Picasso and beyond. Across the street, the Yale Center for British Art has the largest collection outside Great Britain – the building alone is a masterwork. Yale Repertory Theatre is a short walk (Meryl Streep’s early stomping grounds), with area shops in abundance.
Eat: Weigh in on New Haven’s notorious pizza wars: Frank Pepe’s Pizzeria, Sally’s Apizza, or Modern Apizza? If you can’t decide, Miya’s Sushi elevates culinary innovation, with whimsical items like an invasive species menu.
Pick up US-1 N (34 miles; 1 hr)
See: Like gleaming pearls strung near water, these five pretty Connecticut towns edge Long Island Sound along Route 1. Heading west to east, Branford boasts a banquet of restaurants, including Le Petit Café, with an award-winning four-course French bistro menu. Japanese, Indian, Italian, and American options dot the downtown, too. Further east, Guilford’s famous town green is surrounded by shops, with painter Brendan Loughlin’s sunflowers splashed on random doorways, lending a dash of Van Gogh color.
In Madison, there’s stellar beach reading to be had at R.J. Julia Booksellers – a three-minute drive from two miles of sandy heaven at Hammonasset Beach State Park. Bucolic Clinton offers full spectrum shopping: a trove of treasures at the Antique Center on Main Street or 70 outlet stores minutes away at Clinton Crossing Premium Outlets.
Finally, breathe the sea breezes in Old Saybrook, where you can shop the downtown that Kate Hepburn made famous, and cycle along the water out to sun-dappled Fenwick – an idyllic area where the screen legend lived for happy decades.
US-1 N (29 miles; 50 min)
See: It’s one thing to read about cramped ships quarters – it’s another to climb below deck and feel it in an 1841 whaling ship like the Charles W. Morgan, the oldest commercial vessel still in the water. The refurbished ship returns to Old Mystic Seaport – a glorious “living history museum” – in August 2014, after her 38th voyage (this time as a teaching vessel), but meanwhile the 19th-century seafaring village offers up plenty of diversions, with 60 antique buildings and a working shipyard. Complete the high-seas picture with a visit to the beluga whales at the terrific Mystic Aquarium.
Eat: For a slice of movie history, check out Mystic Pizza, in Mystic proper. This cozy joint celebrates the film that was Julia Roberts’s big break, and the movie plays on an endless loop in the background, flavoring every bite.