By Alan Dodd
Squash Hollow is a section of New Milford between Gaylordsville and Boardman. The northern entrance is two miles south of the village of Gaylordsville when it leaves Route 7 and goes in a two mile half circle and comes out near the Citgo gas station in Boardman. Years ago, as a boy, I remember it as having only three families on small farms on a narrow dirt road, with most of the land forest land.
I have heard that in the 1800's there were small farms the entire length of the two miles, with many families living there, and it was the main road between Gaylordsville and New Milford. Some of the settlers thought the hollow was shaped like a squash and so it got its name.
Both my great grandfather Flynn and great grandfather Dodd came from Canada and bought farms there. Grandfather Dodd's farm is now covered with houses and is the largest settlement in the hollow, which now has houses the whole length and a blacktop road.
A story about Squash Hollow is that during the Civil War, money to help the south was sent to Canada and as the southern ports were blockaded, they brought it over land. While going through Squash Hollow, they thought they were going to be caught and buried the money on Round Hill in the Hollow. Civil War historians doubt the story is true, but people at the time thought so and used to go there and dig, looking for the money. They never found it.
I was told by my stepfather that when he was a boy, a man lived in the Hollow who was building a flying machine. They thought he was a nut, but perhaps he was an early genius.
An old map from the mid-1800's shows the name "Page" as living there. Harold and Melvin Page still live in Squash Hollow, and are the last of the old families who still live there.
Jonathan Buck lives in the original Buck house near the south end of Squash Hollow. While the house is not on Squash Hollow Road, some of the farm land was. When the first Mrs. Buck was an elderly lady, she was picking berries around one of Buck's hay lots when she fell dead of a heart attack. Her son placed a stone like a gravestone where she fell as a memorial. Some people thought she was buried there but she was not. I have seen the stone but with all the houses that are built in the area now, I don't know if it is still there.
So Squash Hollow has gone from a thickly-settled place to one occupied by three families and back to a place thickly settled. It took over a century and a half to do it.
Ó 1999 Alan Dodd