Walking the Post Road

Old King’s Highway North in Darien, Connecticut. The large tree at center has a plaque on its trunk that reads “ The International Society of Arboriculture and the National Arborist Association jointly recognize this significant tree in this bicentennial year as having lived here during the American Revolutionary period, 1776-1976.”

“The road was mostly for local travel...but there were wanderers, pedestrians who walked the roads as had their predecessors through the ages: peddlers, fugitives, tramps (both male and female), the itinerant artisans with backpack or packhorse, men who dressed and sharpened millstones or tinkers who mended brass- and tin-wares.”

Kenneth Reiss, The Story of Darien, Connecticut, 45, on the post road in Darien.


  1. 1.Bertha Mather McPherson, editor, Darien, 1641-1820-1970: Historical Sketches (Essex, CT: Darien Historical Society in association with the Pequot press, 1970) 12.

  2. 2.Wood, Turnpikes of New England, 376.

  3. 3.Louise H. McClean, “The Eighteenth Century Tourist in Fairfield County,” in McPherson, 71.

  4. 4.Ibid., 56.

  5. 5.Kenneth M. Reiss, The Story of Darien, Connecticut (Darien, CT: Darien Historical Society, 2009), 46.

  6. 6.Ibid., 18.

  7. 7.Hamilton, Itinerarium, 169.

  8. 8.Ibid.

  9. 9.Washington, Diary, 21.

  10. 10. Birket, Some Cursory Remarks, 38.

  11. 11. Knight, Diary, 71.

  12. 12. Much of this story is told in Stamford 350 Years, 1641-1991, edited by Barry Hoffman et al., and published by The Advocate and the Ferguson Library, manufactured in Hong Kong.  This is the book with an introduction by William F. Buckley, who freely admits to being singularly unimpressed with Stamford on his initial visit in the 1950s but who ended up there serendipitously and grew to like his home of 40 years.

  13. 13.  Another useful book I consulted is Elijah Baldwin Huntington, History of Stamford from its settlement in 1641 to the Present Time, including Darien, which was one of its parishes until 1820 (Stamford: William Gillespie and company, 1868). I love the old titles to history books which seem to explain the whole book to you.

  14. 14.  I have reexamined the old Colles Map around mile 43.5 and have come to the conclusion that the road may have veered around the north side of the hill over which East Main Street (US1) passes rather than climb straight over it, before the two roads merge again at roughly the junction of East Main Street and Lawn Avenue.  I have marked this potential route on the map in red rather than the blue I walked.  In the event Interstate 95 has obliterated a large chunk of what road might have existed from the Noroton River bridge.

  15. 15.  Stamford was not even one of the twelve largest towns in Connecticut in 1774 even though it consisted of Darien, and parts of other towns as well as the area that is today’s Stamford. Today Stamford has about 118,000 inhabitants, making it the fourth largest city in Connecticut, after Bridgeport, Hartford, and New Haven, and the eighth largest in New England, after Boston, Providence, Worcester, and Springfield. By that standard and by the standard of economic success, Stamford is a success story. Certainly, with the exception of Boston, and perhaps Providence, Stamford has the strongest economy of the eight major cities and one of the lowest crime rates.  I still think I would rather live in New Haven or Providence if I could not live in Boston.  That being said, I would pick Stamford over the four remaining cities if I had to choose.

Distance Walked in the Entry: 5.26 miles

Total Distance Walked in Connecticut: 134.66 miles

Total Distance Walked for this Project (from Boston): 305.3 miles

Distance Remaining to New York: 42 miles