The Old Sandwich Road

By Elizabeth Fulford

From the time before history was recorded, there was a footpath winding close to the coast, created by the native Wampanoag people who had a system of footpaths they used for trade, communication, and seasonal migration. Later it became the main road connecting Sandwich and Plymouth (map c. 1705). It still exists, mostly unpaved, winding through the countryside.

Online, I found “Joe’s Retirement Blog” which describes it this way: “Sometimes I walk along and with no other traffic, it seems like I am the only one on the planet. There is barely a sound except an occasional birdsong or a light breeze whispering through the pines to break the silence.”  https://joesretirementblog.blogspot.com/2014/09/old-sandwich-road-plymouth.html  His photo below lets us see what the road looks like today. It is probably the oldest continuously used road in the United States, and, as you may have guessed, it is part of our Wing Family story.

In 1637, the Colony of Plymouth granted the Ten Men of Saugus (now Lynn, MA) a

wilderness area to settle so that “they shall have liberty to view a place to sitt down & have sufficient lands for three score famylies, upon the conditions propounded to them by the Governor and Mr. Winslowe.”  

So, the Ten Men of Saugus and the three score (sixty) families walked the sixty miles from Saugus to an area in the wilderness where they would create Sandwich. The settlement began under very favorable auspices although it was not incorporated as a town until about two years after.

We have no documented proof of the route those families took, but it is probable that they walked on the Wampanoag trail for the last four miles of their journey. Among these families were the Wing brothers: John, Daniel and Stephen.

Later, when the Plymouth government was turning the Wampanoag trail into a road for trade and defense they began referring to it as the Old Sandwich Road. They made a few improvements to it over the years, but it still remained a footpath.

Daniel Wing, who had espoused the Quaker faith in 1657, made frequent trips on the road, going to Plymouth to pay the fines levied on him by the colonial government. He was fined 20 shillings for entertaining Quakers in his home and 20 pounds for refusing to take the "oath of fidelity". In December 1658, he lost his status as a freeman.  Eventually, Daniel’s rights were restored, and in 1669 he was appointed as one of two official surveyors of the highways. When he assumed that position, he wanted to improve the Old Sandwich Road, and he spent a fair amount of time clearing and widening it to make it passable for wagons and riders.

By all accounts, it remains in rough condition today, but it is still used for traffic and hiking.