• Mayflower, Plimouth Plantation, Massachusetts
    The Mayflower, Plimouth Plantation
    Plymouth, Massachusetts

Living History & Rural Relaxation

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Massachusetts, Connecticut, & Rhode Island

This is a relatively short but beautiful easy-to-drive route that links five classic small New England communities in three states. To get the best out of each of the stopovers, stay two or three nights and spend time following 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 and finish in Boston, Massachusetts. Spend a couple of days here to see the sights. The “T,” the public transport system, is efficient and inexpensive — and Boston is the most walkable major U.S city, so, you don’t need to rent a car until you are setting off.
  • Driving distance: About 275 miles
  • Allow 10-12 days
  • View a Google map of this suggested trip

Start: Drive west to Old Sturbridge Village, Massachusetts (60 miles/100 km)

OSV foliage photo - Jeffrey hammond-p5

Old Sturbridge Village, Massachusetts

New England has several outstanding living history outdoor museums. This one recreates the rural village life of the early 19th century, with bakers making bread and blacksmiths hammering out horseshoes. In the 200 acres (80 hectares), horses pull plows and, in the fall, an ox drives the traditional cider mill.


  • Pick your own: This is apple country, and the Tuttle family grows 18 varieties at Breezelands in Warren. Eat apple donuts or crunch them straight from the tree!
  • Discover the ‘Last Green Valley’: This National Heritage Corridor is one of the last unspoiled rural areas of New England. Take a free guided walk during "Walktober."
  • Hike the Mid-State Trail: The route cuts through Central Massachusetts for 95 miles/150 km, but you can do just a portion: in the quiet of Douglas State Forest, near Webster.

Take the short drive south into northeastern Connecticut, known as the Quiet Corner. Stay in or near Woodstock (15 miles/25 km)

Roseland Cottage Bowen House, Woodstock, Connecticut

Woodstock, Connecticut

Actually covering six villages (South Woodstock, Woodstock Hill, North Woodstock, East Woodstock, West Woodstock, and Woodstock Valley), peaceful Woodstock offers antique shops, crafts shops, farms, and charming bed and breakfasts.


  • Travel back to 1846: Visit Roseland Cottage, a Gothic Revival summer retreat, with a fine 19th-century landscaped garden.
  • Cry wolf: Hike in Mashamoquet Brook State Park. Peer into the Wolf Den, where Israel Putnam killed a predatory wolf back in 1742 — according to legend.
  • Follow Route 169: Parallel to the Rhode Island border, this is one of the U.S.A.’s prettiest country roads, linking historic hamlets: Pomfret, Brooklyn, and Canterbury.

Drive south to Norwich. Take Route 2 to Westerly, just across the Rhode Island border (55 miles/90 km)

Westerly, Watch Hill, Rhode Island, Flying Horse PC 07 - Kathy Marciante 1 - 300 dpi 2x3

Westerly, Rhode Island

On the Pawcatuck River, this town makes a popular base for nearby sandy, family-friendly beaches and, in Watch Hill, the Flying Horse Carousel. Built in 1876, it is one of the oldest of its kind in the U.S., with beautifully-carved wooden horses.


  • Watch the fireworks: The free Guy Fawkes Bonfire Night brings music, theater, a bonfire, fireworks, and more to Misquamicut Beach.
  • Delve into the past: Stonington (just across the Connecticut line) dates from 1649. Colonial, Federal and Greek Revival houses stand on tree-lined streets; the port is home to the state’s only surviving commercial fishing fleet.
  • Step into the Gilded Age: Newport is a must-see destination. Go for the opulent mansions, built by the Vanderbilts and their friends in the late 19th century — and for the Colonial history.

Drive along the South County Coast through Narragansett, Newport, and Portsmouth to Bristol (60 miles/100 km)

Coggeshall Farm Museum - Bristol, Rhode Island

Bristol, Rhode Island

In one of “America’s Distinctive Destinations,” the Fourth of July celebrations — held annually since 1785 — are the country’s oldest! Almost totally surrounded by water, the town’s long history of boat building is told at the Herreshoff Marine Museum and America's Cup Hall of Fame. Nearby, the 300 different tree species provide fall color at Blithewold Mansion, Gardens and Arboretum.


    • Enjoy simple pleasures: At Coggeshall Farm Museum, Bristol, the clocks stopped in 1799. Fall events include a Harvest Fair, hearth cooking, and pressing fresh apple cider!
    • Cycle the shore: The paved, well-marked East Bay Bicycle Path follows Narragansett Bay for 14 miles/22 km, from Bristol to Providence. Stop at the Audubon Society of RI Environmental Education Center to spot migratory birds.
    • Get away from it all: The 265-year-old Mount Hope Farm combines farmland, wetlands, farm buildings, and more on 200 acres (80 hectares).

    Drive through southeastern Massachusetts to Plymouth, where the Pilgrim Fathers settled in 1620 (50 miles/80 km)

    Plimoth Plantation - Pilgrim mother & child (credit-Plimoth Plantation)

    Plymouth, Massachusetts

    “America’s Hometown” is all about the Pilgrims, who sailed across the Atlantic nearly 400 years ago. See the memorial at Plymouth Rock, board Mayflower II, the full-scale reproduction of the Pilgrims’ 17th-century vessel, and see how they lived at nearby Plimoth Plantation.

    • Learn about Thanksgiving: Plimoth Plantation explains the facts (and the fiction) about the country’s favorite national holiday — that started right here!
    • Enjoy the harvest: Cranberries are the state’s number one crop and turn bogs brilliant red at harvest time. Also fun is Edaville’s National Cranberry Festival.
    • Go whale watching: Seeing a whale “breach” (leap out of the water) is a thrill for the whole family. Take warm clothes and sunblock.

    Return to Boston, MA (40 miles/65 km)