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US Route 20 extends from the east coast to the west coast of the United States. Through Massachusetts, it parallels colonial routes taken during the Revolutionary War by George Washington, Henry Knox, Paul Revere and William Dawes, the prisoners of Saratoga, the soldiers of Shays’ Rebellion as well as personnel, supplies and communications. The colonial routes of Massachusetts were deemed far enough inland to be safe from enemy attack.

At the beginning of the summer of 1775, George Washington followed the colonial route to Boston to take command of the Continental Army. There are several markers on US Route 20 denoting it as the George Washington Memorial Highway.

Three months earlier, Paul Revere and William Dawes made their famous midnight rides to warn the countryside that the British were coming. The routes they took were about five miles north of today’s US Route 20.

About nine months later, Henry Knox and his train of artillery from Fort Ticonderoga crossed Massachusetts on its way to end the siege of Boston. There are more than ten markers denoting the “Knox Trail” and many are within a few yards of US Route 20.

After the Battles of Saratoga in the fall of 1777, British prisoners were taken to Boston along colonial routes from New York State. The reception the prisoners received at the many towns and villages along the way varied from a warm friendly greeting to cold disdain.

During the winter of 1786-1787, three years after the formal end of the Revolutionary War, the battle continued over unfair taxes in western Massachusetts. Shays’ Rebellion is often called the last battle of the Revolutionary War because it was the catalyst that caused the final pieces of the newly formed US Government to fall into place. Several events from Shays’ Rebellion occurred along today’s US Route 20 including the “final battle” near Great Barrington and Shays’ attempt to take the colonial armory in Springfield.

A Revolutionary Day Along Historic US Route 20
begins early in the morning at Pittsfield, Massachusetts. In the late fall of 1775, Henry Knox passed through the village of Pittsfield on his way to organize a transportation unit in New York to carry the cannons captured at Fort Ticonderoga to Boston.

From Pittsfield, the road trip heads south through Lenox and Stockbridge and then west to the New York State border to pick up the Knox Trail to Great Barrington. Along the trail is the site of the last battle of Shays’ Rebellion.

From Great Barrington, the road trip crosses over the scenic Berkshire Mountains through Monterey, Otis and Blandford to Westfield where Knox celebrated the near completion of his transportation mission, an ordeal that many called impossible.

From Westfield, the road trip heads east through West Springfield to Springfield, which was the home of a colonial armory that made Springfield a Revolutionary War crossroad.

From Springfield, the road trip continues east through Wilbraham, Palmer, Brimfield, Sturbridge, Charlton, Oxford, Auburn, Worcester, Shrewsbury, Northborough, Marlborough to Sudbury and the Wayside Inn where the gathering of patriots and guests have been immortalized by Longfellow’s Tales of a Wayside Inn.

From Sudbury, the road trip takes a turn to the north through Wayland and by Walden Pond to Concord, which was a target of a British penetration on April 19, 1775.

From Concord, the road trip heads east along the “Battle Road” from Concord through Lexington and Arlington to Bunker Hill, where Americans would try to stop British expansion around Boston.

From Bunker Hill, the road trip concludes with a walk along the Freedom Trail through Charleston and the North End to downtown Boston passing by many of Boston’s historic colonial sites including, Old North Church, the Paul Revere House, Faneuil Hall, the Old State House, the Old South Meeting House, Granary Burying Ground and Boston Common.

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