1. New Haven, CT


2 hours from NYC
New Haven may be best known for being the home of Yale University but there’s plenty to explore in this charming cultural capital even without a coveted acceptance letter. From the restaurants and shops on Chapel St. to the delicious, dueling “apizza” joints, there’s more than enough to keep you busy for a full weekend. On top of that, almost all of the small city’s world-class museums are completely free.
Do this: After a multi-year renovation, the Yale Center for British Art recently reopened to once again welcome visitors to its fascinating exhibitions. Widely thought to have the greatest collection of British art outside of the UK, this must-visit institution is housed in a striking, brutalist Louis Kahn building that’s a work of art in itself. (While you’re there, be sure to stop by the similarly gratis Yale University Art Gallery and Yale Peabody Museum.) No trip to New Haven would be complete without a trip to Sally’s Apizza or Frank Pepe Pizzeria Napoletana to sample the local take on a pizza pie. (It’s kind of like an NY slice but with a chewier crust.) For a night out, make a reservation at Tavern on State for elevated cuisine.
Stay here: With a desirable location right on Chapel St., The Study at Yale has a modern feel with a fantastic on-site restaurant: Heirloom. Another great local option for travelers is The Blake Hotel which boasts large suites and has a fun rooftop bar space.