Someone asked me recently how Connecticut ended up with such an unusual "panhandle" boundary with New York. Some people even say it would make more sense for Greenwich to be part of New York. Geographically it makes sense. Who wouldn't want this wealthy community as part of their state?
The panhandle boundary resulted from a series of historical events, disagreements and compromises with the English and Dutch over many years. In the early 1600s, both the English and Dutch had established settlements in Connecticut. After discovering what came to be known as Block Island in 1614, Dutchman Adriaen Block sailed around Long Island Sound, exploring many inlets along the southern coast of Connecticut. He charted Block Island, which is named after him. By 1633 the Dutch had built a fort at Hartford, and claimed land as far east as the Connecticut River. The English countered by settling Windsor, Wethersfield and Hartford. A Dutch expedition was sent to try to force the English out, but war was averted when an agreement was reached in 1650. The settlements became part of the New Haven Colony, and a boundary was set on the west side of Greenwich Bay running north approximately 20 miles, but not to come within 10 miles of the Hudson River.
Then the dispute was again revived by a royal blunder. The Dutch surrendered the New Netherlands (the Hudson River valley region from Albany to New York City) after two short wars (1652-1654, 1664). Charles II of England had granted Connecticut lands that stretched westward all the way to the Pacific Ocean in 1662. In 1664, when England took over the New Netherlands (soon to become New York), Charles II gave lands to his brother (the Duke of York) that stretched from New York east to the Connecticut River. As you can see, this resulted in overlap of ownership by New York and Connecticut. The colonies compromised, and agreed to set the boundary 20-miles east and parallel to the Hudson River.
Ironically, several weeks later Connecticut commissioners persuaded the Duke of York's representative to establish a boundary from Mamaroneck north-north-westerly to the Massachusetts border. Instead of being 20-miles from the Hudson, the border was only 10-miles from the river. Also, the line did not , in fact, intersect the Massachusetts border, but crossed the Hudson near West Point. This added a significant amount of land to Connecticut at the expense of the New York colony. This was not acceptable to New York!
Another compromise was reached in 1683. Connecticut was concerned about losing several important, well-established towns such as Greenwich and Ridgefield. Yet, New York was concerned about losing large tracts of land represented by these towns. It was agreed that Connecticut would retain these lands, while an equivalent tract of land named the "oblong" would be given to New York as compensation. This was a two-mile wide strip of land running north from Ridgefield up to Massachusetts, and moved the New York boundary further east. A slight "wiggle" was required to keep Ridgefield in Connecticut. After this equitable exchange of land, New York and Connecticut agreed on the present configuration, which recognizes Greenwich and Ridgefield as part of Connecticut while observing the 20-mile requirement.
In 1684, a survey was begun to establish the boundary once and for all. It was only partially completed. It wasn't until 1731 that a complete survey was completed. There are markers all along the boundary. Today, there is a marker in the Byram River near the Mill Street Bridge which marks the southern most end of the boundry.
Greenwich Old & New; Holland, L. and Leaf, M.; The Greenwich Press, 1935.
Ye Historie of Ye Town of Greenwich; Mead, S; The Knickerbocker Press, NY; 1911