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The spot of the trading post is at the confluence of the Farmington and Connecticut Rivers.The Loomis Chaffee School currently owns the land as the spot is now the school's sports fields.Outraged, Springfield forever sided with the Massachusetts Bay Colony, a faraway theocracy based in Boston, rather than with the Connecticut Colony, which was much closer geographically and far more compatible ideologically.Windsor played a neutral role in the colonial rivalry between Hartford and Springfield; however, Windsor's direct border with both settlements caused many discussions about whether to align with Massachusetts or Connecticut. The Hartford & Springfield Street Railway, a trolley, connected with the Connecticut Company in Windsor Center until 1925.
It was about 50 miles (80 km) up river from Long Island Sound, at the end of waters navigable by ship and above the Dutch fort at Hartford, offering an advantageous location for the English to trade with the Indians before they reached the Dutch.
The first "highway" in the Connecticut Colony opened in 1638 between Windsor and Hartford.