• Yale University Art Gallery
    Yale University Art Gallery

Art, History and Natural Beauty

Connecticut & Massachusetts

In New England, the fall foliage is Mother Nature’s annual free gift. In September and October, leaves turn to gold, scarlet, purple, and yellow. See them from a car, bus, or train. Or, from a boat or a mountain top, while peddling a bike or following a hiking trail. To get the best out this route that leads to rivers, unspoiled countryside and great art museums, stay 2 or 3 nights in each of the 5 stopovers and follow our top tips.

Trip ideas and itineraries are meant as suggestions only. They are intended as ideas and to highlight all there is to see and do in New England.

  • Start in New York, end in Boston.
  • Driving distance: About 400 miles/650 km.
  • Allow 10-12 days.
  • View this tour in Google Maps.

From New York, head for New Haven, Connecticut (80 miles/130km).

New Haven, Connecticut (credit-Kindra Clineff)

New Haven, Connecticut

The city is home to Yale University and its 12,000 students, and the University's own art gallery plus the Yale Center for British Art, the best collection of British works outside the United Kingdom.


  • The 80-minute, student-led walking tour of the Yale campus.
  • The self-guided Public Art Tour of the 22 outdoor installations on campus.
  • An architecture tour highlighting buildings from the 18th century to modern masterpieces designed by Louis Kahn, Paul Rudolph and Eero Saarinen.

Drive to Litchfield, Connecticut (60 miles/100km) along scenic Route 10, via Cheshire, and stop by the Hill-Stead Museum, a fine old mansion known for its Impressionist collection and grand gardens.

West Cornwall Fall Road - (Credit-Western CT Convention and Visitors Bureau)

Litchfield, Connecticut

The small town of Litchfield looks like a film set with its lovingly preserved streets and houses, shops and restaurants. This is why New Yorkers love to weekend here.


Follow the Housatonic River along Route 7, one of the state’s loveliest roads. Cross into Massachusetts, where Route 7 links picturesque towns, such as Sheffield (antiques) and Great Barrington. Stay in Stockbridge, Massachusetts (60 miles/100km).

Autumn View from the Clark Museum - Massachusetts

Stockbridge, Massachusetts

Seemingly unchanged since Norman Rockwell painted it 50 years ago, the Main Street is 100% New England: sidewalks and white picket fences, clapboard homes and hardware stores. Sit on the porch of the 1773 Red Lion Inn and watch the world go by.


  • The Norman Rockwell Museum: The world’s largest collection of paintings by America's best-loved artist and the studio where he worked.
  • Chesterwood: The home, studio and gardens of America's most recognizable sculptor, Daniel Chester French.
  • Naumkeag House & Gardens: an architectural masterpiece with echoes of America's Gilded Age.

Carry on northwards through charming Lenox to Williamstown with its college and the world-class Clark Art Institute (French Impressionists, Old Masters) in a stunning fall setting. Carry on to North Adams and Mass MoCA, one of America's largest centers for contemporary visual and performing arts, located in renovated 19th-century factory buildings. Drive the Mohawk Trail, one of America’s first scenic automobile routes. Look for the roadside “Hail to the Sunrise” Mohawk statue near Charlemont, and the Bridge of Flowers, a garden on an old trolley bridge, in Shelburne Falls. Continue to Deerfield, Massachusetts. (80 miles/130 km).

Wapping School House, Historic Deerfield, Massachusetts (credit-Historic Deerfield)

Deerfield, Massachusetts

“The Street” is Historic Deerfield’s picture-perfect main thoroughfare, lined with 65 beautifully-preserved 18th and 19th-century houses. Most are private homes; eleven are now excellent museums devoted to New England heritage, as is the impressive Flynt Center of Early New England Life.


  • Take a cruise: Northfield Mountain Recreational Area offers fall foliage trips on the Connecticut River aboard the Quinnetukut II Riverboat.
  • Zip through nature: Zoar Outdoor Zipline is a thrilling but safe ride: 3 hours, 11 ziplines, 3 rappels, 2 sky bridges.
  • Ride a trolley: Board an 1896 trolley at the Shelburne Falls Trolley Museum for a fall foliage ride.

Drive east on Route 2 to Concord (80 miles/130km). En route, take a diversion to Davis Mega Maze, New England's largest cornfield maze!

DeCordova Sculpture Park and Museum - Autumn

Concord, Massachusetts

Forever linked with the opening skirmishes of the American Revolution, Concord actually dates back to 1635. This charming community has a large green, white clapboard homes, restaurants and small museums.


  • Concord is linked to Lexington and its Battle Green by Minute Man National Historical Park: explore both aboard the Liberty Ride ‘hop-on, hop-off’ trolley tour.
  • Visit Louisa May Alcott's Orchard House: During America’s 19th-century literary revolution this was the setting for her novel Little Women.
  • Visit the DeCordova Museum in nearby Lincoln: New England's largest outdoor sculpture park (more than 60 modern and contemporary works) covers 30 acres, and is glorious in fall.

Drive back to Boston (20 miles/32km).