Boston Post Road - Upper Post Road

The Upper Post Road was the most traveled of the three routes, being the furthest from the shore and thus having the fewest and shortest river crossings. It was also considered to have the best taverns, which contributed to its popularity. The Upper Post Road roughly corresponds to the alignment of U.S. Route 5 from New Haven, Connecticut, to Hartford; Connecticut Route 159 from Hartford to Springfield, Massachusetts; U.S. Route 20 from Springfield to Warren, Massachusetts (via Route 67); Massachusetts Route 9 from Warren through Worcester to Shrewsbury; and U.S. Route 20 from Shrewsbury to Boston. A series of historic milestones erected in the 18th century survive along its route from Springfield to Boston.

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