Why is New England so rich in art museums? As a cultural center from America’s earliest days, it has long been home to wealthy patrons and art collectors—but it’s also a region where many artists chose to live and work. The combination of the two gives this six-state region an incredible number of top art museums. The challenge is to fit them all into one trip. In this itinerary, we focus on museums with outstanding collections of American art, a particular strength in this region.
If you’re starting out from Boston, we’ll just assume you’ve already visited its two great art museums, the Museum of Fine Arts and the Isabella Stewart Gardner Museum. If not, head back to Boston at the end of this itinerary to take them in: Both are world-class repositories of art. 
Day 1: Portland, ME
Arriving in Portland, make a beeline for the Portland Museum of Art, a stunning modern space right downtown. The museum’s permanent collection is broad, but one of its strengths is Maine landscapes by such American masters as Winslow Homer and Andrew Wyeth. If you’re on a summer Monday or Friday, be sure to make a reservation to visit Winslow Homer’s studio, out on nearby Cape Elizabeth—you’ll understand better than ever this master’s connection to the rocky surf-battered coast of New England. 
Day 2: Ogunquit, ME
Driving south from Portland, if you’re here between May and October, an essential stop is this small beach town, 45 minutes south of Portland, which just happens to have one of the best small museums in New England. Thanks to Ogunquit’s role as an artists’ colony since the 1890s, the Ogunquit Museum of American Art has rich holdings in early Modernist works by such Ogunquit painters as Charles Woodbury, Hamilton Easter Field, and Robert Laurent, as well as the Modernist “painter of Maine” Marsden Hartley. Be sure to wander around the sculpture garden overlooking Perkins Cove. Spend your morning here, grab lunch, and then drive on to tonight’s base, Worcester, MA (take I-95 to I-395 and you should be there in 2 hours). Worcester has increasingly been developing a foodie scene. Hopefully you’ve planned ahead and made reservations at the popular gastropub Armsby Abbey; otherwise, head for the Shrewsbury Street restaurant strip, where you should do well at any number of restaurants.
Day 3: Worcester, MA & Hartford, CT
As this formerly gritty mid-Massachusetts city is rapidly upgrading its image, a major factor has been the well-regarded Worcester Museum of Art. Head straight for its American wing to drink in masterpieces by Mary Cassatt, John Singer Sargent, and James Whistler, who in the late 1800s won respect for American painters in European salons. Leave after lunch, taking the Mass Pike to I-84; in about an hour you’ll be in Hartford, Connecticut. In the heart of downtown, the venerable Wadsworth Atheneum, opened in 1844, is the U.S.’s oldest art museum. It’s easy to get distracted by all the marvels in this rambling complex, but head straight for level 3 to focus on its American art, including an amazing stash of Hudson River School landscapes. Back on level 1, the contemporary art collection brings you up to date with works by everyone from De Kooning and Pollock to Sol LeWitt and Cindy Sherman.
If you leave by 5pm, getting onto I-91, you should be in New Haven, CT, by dinnertime—it’s only a 40-minute drive. New Haven will be your base for the next two nights. Grab a pizza at any of New Haven’s storied pizza joints.
Day 4: New Haven, CT
You could spend a full day in New Haven, strolling around the Yale University campus. With art as your focus, however, you’ll probably want to do most of that strolling inside the university’s two excellent art collections. The Yale University Art Gallery has one of the best collections of American art of any museum in the country. Start on the second floor to see treasures of early American art (Trumbull and Copley portraits et cetera), then come down to the first floor to find numerous paintings by American realists of the late 19th and early 20th centuries. And then—well, it’s not American art, but while you’re here you’ll probably also enjoy visiting the Yale Center for British Art, the richest repository of British art outside of the U.K. If you haven’t scored a reservation at the Union League Café for tonight, try your best to get into Heirloom or Zinc.
Days 5, 6 & 7: The Berkshires
On Day 5, set out right after breakfast to make the 2-hour drive (Route 8 north to the Mass Pike) to the Berkshire Hills, at the western end of Massachusetts. Base yourself in either Lenox or Williamstown for the next three nights. Your main problem here will be deciding which museums to see first. We recommend pairing museums that are closer to each other. For example, on one day combine a stop at Lenox’s Frelinghuysen Morris House, where abstract artists Suzy Frelinghuysen and George L.K. Morris lived, with a visit to the Norman Rockwell Museum in nearby Stockbridge, dedicated to the work of the great 20th-century magazine illustrator. About 20 minutes from Lenox, you’ll also find the Berkshire Museum in Pittsfield, a mix of natural history, history, and art museum; head for the second floor to find 19th-century landscapes by such masters as George Inness, Edwin Church, and Albert Bierstadt. 
Farther north, Williamstown has not one but two outstanding museums: the Williams College Museum of Art, where you’ll find works by Whistler, Warhol, and Hopper, as well as a cache of modernist paintings by Maurice and Charles Prendergast; and the Clark Art Institute, which focuses on 19th century European art, but also has works by John Singer Sargent and Winslow Homer. A 20-minute drive north up Route 7 will take you to Bennington, VT, where the Bennington Museum has the world’s largest collection of paintings by Grandma Moses. And it’s only a few minutes’ drive from Williamstown to North Adams, where the superb Massachusetts Museum of Contemporary Art (MASS MoCA), always has something interesting going on. MASS MoCA also features lots of eclectic performing arts—check in advance what’s on, to coordinate your visit with a performance you’d enjoy. 
While you’re in the Berkshires, make time for shopping in Great Barrington, antiquing in Sheffield and Lenox, and some outdoor walks in any of the region’s beautiful parks. If you plan ahead, you may also be able to score tickets to one of the area’s great summer arts festivals: Tanglewood or Marlboro for music, Jacob’s Pillow for dance, and the Williamstown Theater Festival for theater. The Barrington Stage Company in Pittsfield, The Berkshire Theatre Festival in Stockbridge, and Shakespeare & Company in Lenox also ramp up their performance schedule in the summer season. There’s no shortage of things to do here! 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.