Itinerary #14: New England Road Trip

I knew New England would be rich with historical significance, but I had no idea it would be so overwhelming.  I felt at times that I was standing in the birthplace of this great nation.  Seeing these historic places, pulled at us and brought us close to those brave souls who were pushed to the edge, to risk life and limb for liberty and freedom.  From John Adams to JFK to Ben and Jerry, New England was full of people who were not afraid to be forward thinkers and test the boundaries of new ideas. There was so much to love about New England that was so unique and different from other parts of the country: Maine’s unspoiled natural beauty, New Hampshire’s spirit to “Live Free of Die”, Massachusetts pride as the bloody birthplace of our nation, Rhode Island’s graceful nod to tolerance and religious freedom, and Vermont’s rural pastures that gently roll with a slightly offbeat tempo.  Whether you follow our itinerary here, or create your own, any trip to New England will take you deep within the heart of what makes America great.

States Massachusetts, Rhode Island, Connecticut, Vermont, New Hampshire, Maine

Theme Rebels and Revolutionary IdeasDuration 11 Days | Map


Day 1: Fly or Drive to Boston

Day One

Day 2: Explore Boston

Boston Tea Party Ship and MuseumMIT
Harvard University
Boston Tea Party Ship and Museum
Massachusetts State House
The Freedom Trail
Lunch around Faneuil Hall
Dinner in the North End (Sample some Italian fare)

Day 3: Boston to Cape Cod

Cape CodJFK Presidential Library
Adams National Park (Quincy)
Plymouth Rock (Plymouth)
Plimoth Plantation (Plymouth)
• Harbor Cruise Hyannis Harbor
• Cape Cod Potato Chip Factory Tour

Day 4: Cape Cod to Providence, RI

America's Cup ChartersExplore Cape Cod
• Visit Newport Mansions, The Breakers (Newport, RI)
Touro Synagogue (Newport, RI)
America’s Cup Charter Cruise (Newport, RI)
• Drive to Providence

Day 5: Providence to Hartford, Connecticut

YaleRhode Island Statehouse
• Rhode Island Historical Society
Yale University (New Haven, CT)
Pez Visitor Center (Orange, CT)
Mark Twain’s House (Hartford, CT)
Connecticut State House (Hartford, CT)

Day 6: Hartford to Burlington, Vermont

VermontBasketball Hall of Fame (Springfield, Mass)
Norman Rockwell Museum (Stockridge, Mass)
Dakin Farms, (Ferrisburgh, VT)
• Vermont Teddy Bear Factory (Shelbourne, VT)
• Drive to Burlington

Day 7: Burlington to Porsmouth, New Hampshire

New Hampshire State Capitol BuildingBen and Jerry’s Factory Tour (Waterbury, VT)
Vermont State House (Montpelier, VT)
Cabot Creamery (Cabot, VT)
• Billings Farm and Museum (Woodstock, VT)
New Hampshire Statehouse (Concord, NH)
• American Independence Museum (Exeter, NH)
• Drive to Portsmouth

Day 8: Portsmouth to Ellsworth, Maine

L.L. Bean Flagship StoreL.L. Bean Flagship Store (Freeport, ME)
Thomas Moser Factory Tour (Auburn, ME)
Maine Statehouse (Augusta, ME)
Maine State Museum (August, ME)
• Drive to Ellsworth

Day 9: Ellsworth to Portland

Lobster Fishing on the Sarah MeadAcadia National Park
Pick Wild Blueberries (If in season, for farms click here)
Lobster Fishing (Various locations)
• Drive to Portland

Day 10: Portland to Boston, Massachusetts

Portland Head LightPortland Head Light
Boott Cotton Mills Museum (Lowell, MA)
American Textile Museum (Lowell, MA)
Minute Man National Park (Lexington and Concord, MA)
• House of the Seven Gables (Salem, MA)
Fisherman’s Memorial (Gloucester, MA)
• Drive to Boston

Day 11: Head Home


  1. This was one of our fav trips, you have given us some fresh ideas to use when we repeat it.