I found this story in a Portsmouth newspaper published in 1808. I cannot swear to its accuracy. I rather suspect that it is just one of those yarns that are swapped among the village loafers sitting in the local tavern or country store. With each retelling the tale will be “improved” by the story teller.
It seems that an Ulster Irishman arrived in the early spring to the port of Boston. He knew no one in the area and was eager to get to Londonderry. There, he knew a lot of men who had earlier emigrated from across the sea. Londonderry was at this time made up of the present day towns of Derry and Londonderry. The newly arrived traveler thought that the frontier town of Londonderry would be a good place to settle and make his fortune.
Near the wharf in Boston he rented a one-horse cart to carry his belongings to his future home. The roads in the city were fine and he found himself making good time in the first phase of the 50 mile trek to Londonderry. However, as soon as he left the city limits, the traveling conditions began to deteriorate. Paved avenues became gravel roads, and then soon degenerated into narrow dirt paths with a mane of grass running up the center. The road went up and down hills that were both steep and rocky. He also found his forward progress was slow because the course of the road was about as straight as the vines in a pumpkin patch. What looked like a few hours travel took two days and he had to sleep in his wagon on the side of the road.
As the emigrant crossed over into New Hampshire, the so-called highways got even worse. The roads were so narrow that the brush on the side of the road hit his face as he rode by. In the dark, these trees’ limbs looked like banshee’s arms trying to snatch him off his cart. As if the rocky, rutty, hilly and crocked road conditions weren’t bad enough, it was also mud-time and black fly season in New Hampshire.