Boston  isn’t called the “Athens of America” for nothing—it’s one of the country’s premier outlets of art and culture. You can craft a whole itinerary from the art and theater in New England’s cities and college towns. Boston’s art scene gets hopping in the fall and spring; in the summer, the action moves to the southern shores and the Berkshires.
On your second day, stroll along Newbury Street in the morning, checking out its many art galleries . In the afternoon, visit the one-of-a-kind Isabella Stewart Gardner Museum  or the new waterfront Institute of Contemporary Art .
Head south along I-95 to Providence  (one hour), where you can check out the cutting-edge modern art museum at Rhode Island School of Design  and browse the funky shops around Brown University . At night, catch an experimental performance at the acclaimed Trinity Repertory Theatre  or, if the timing is right, attend the Waterfire  performance on the river.
Head up Interstates 295, 90, and 91 back into Massachusetts  to visit Northampton  (2.5 hours), one of the most delightful college towns in New England. Visit Smith College , treat yourself to a wide selection of ethnic food, and take in a folk music performance at night.
Head down I-90 and up Route 20 to Lenox  (2 hours), where, depending on the season, you can catch the Boston Symphony Orchestra  at their summer home of Tanglewood , a performance at the annual Jacob’s Pillow Dance Festival , or a production by the Commonwealth Shakespeare Company  at their reconstructed Rose Playhouse. While you’re there, don’t miss the flower gardens at The Mount , a work of art to rival any museum.
Another day, another college—head up Route 7 to Williamstown  (one hour) and tour beautiful Williams College . While there, take in the college art museum and the spectacular collection at the Clark Art Museum . If you’re lucky, you’ll catch a performance at the Williamstown Theatre Festival , which has drawn such actors as Ethan Hawke and Marisa Tomei.
While staying in Williamstown, take a side trip down Route 2 to North Adams  (20 minutes), a rejuvenated mill town that’s home to the gargantuan Massachusetts Museum of Contemporary Art  and countless galleries. After dinner, stick around for the town’s funky nightlife.
Drive up Route 7 to Bennington  (30 minutes) and check out the famous folk art of Grandma Moses at the Bennington Museum . Then cross southern Vermont  along Route 9 to Brattleboro  (one hour), home to a thriving café and gallery scene . If the season’s right, take in a traditional music concert in Marlboro , or one of the acclaimed barn concerts in Putney, before bedding down in Brattleboro. Tomorrow, take the express trip back to Boston , along I-91 and Route 2 (2 hours). Leave room in your luggage for your own unique art finds!