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The Longmeadow Border Jog

If you have ever looked at a map of Massachusetts and Connecticut, for the most part, the border between the two is a straight line. That being said, there are exceptions and one of them exists in Longmeadow.

(Credit Google Maps)

The above map clearly shows a dramatic dip in the border as it crosses the Connecticut River followed by a straight line, a quick slant and then a more gradual angle until it seems to level out again around the East Longmeadow line. Why is the border between these two states not a straight line here? It turns out we have the founder of Springfield, two lazy surveyors, and the founders of Enfield to thank for this anomaly.

Our story starts with William Pynchon who founded Agawam Plantation (now modern day Hampden County and Enfield, Somers, and Suffield, CT) on land purchased from the Agawam people. in 1636. Pynchon decided on the spot for a settlement because it was situated on a high bluff overlooking the confluence of three rivers, the Connecticut, the Chicopee, and the Westfield Rivers, making it an ideal spot for a trading post. And while Pynchon had been treasurer of the Massachusetts Bay Colony, the settlement he founded was administered as part of the Connecticut Colony along with the much more geographically closer Wethersfield, Windsor, and Hartford.

(William Pynchon Credit Wikipedia)

For the first four years of its existence, Agawam Plantation was administered as part of Connecticut. That began to change in 1640 when grain supplies began to run low due to a poor harvest the previous fall and cattle began to die of starvation as a result. In an effort to improve the situation, Windsor and Hartford authorized Pynchon to negotiate the purchase of corn for all three communities from the Pocumtuc people near Agawam Plantation. When Pynchon failed to secure the corn, according to early 20th century historian Charles Henry Barrows, the other three communities in the colony sent Pequot War veteran Captain John Mason with “money in one hand and a sword in the other” to secure the much needed feed. While Mason was able to obtain the corn, he upset the settlers of Agawam Plantation with his heavy handed tactics with their Pocumtuc trading partners and his public insult of Pynchon’s previous efforts. As a result, the settlers voted to separate themselves from the Connecticut colony and joined the Massachusetts Bay Colony as the Town of Springfield, named for Pynchon’s hometown in England, later that year.

In part because of the secession of Springfield, the Massachusetts Bay Colony authorized an expedition to survey its southern border with Rhode Island and Connecticut to verify its territorial claims in 1642. The survey group, led by Nathaniel Woodward and Solomon Saffery, failed to do a rigorous survey. Instead of traveling over land for their survey, Saffery and Woodward marked the established southern border point of three miles south of the southernmost branch of the Charles River and then sailed around Cape Cod and up the Connecticut River to where they believed was parallel with the established border point. The problem was that they were off by a little over seven miles which placed Enfield in Massachusetts.

(Map showing Connecticut’s various border disputes with its neighbors: Credit William F. Keegan via Wikipedia)

While Connecticut protested the results of the survey, they didn’t get around to doing their own survey to dispute it until 1695. In the meantime, the town of Freshwater Plantation, MA (now Enfield, CT) was incorporated in 1683. At that time, the border between the newly formed town and Longmeadow (then part of Springfield) was established as the banks of the Longmeadow River (now known as Longmeadow Brook which has changed course considerably to the north). This boundary was made without any consideration of any colonial charter dictates because both towns firmly believed that they were within Massachusetts’ legal boundaries.

After Connecticut’s 1695 survey cast some serious doubts on the accuracy of the 1642 survey, Massachusetts and Connecticut agreed to a joint survey in 1702 that reaffirmed the accuracy of the 1695 one. In an effort to avert intervention from the English Crown in the dispute, Connecticut agreed to sell Massachusetts the disputed territory in 1713. Unfortunately, those living in this fought-over land were not consulted and disliked the decision because Massachusetts had higher taxes and fewer civil liberties when compared to its southern neighbor. Eventually, Connecticut reversed itself on the sale and in 1749 the towns of Enfield, Somers, Suffield, and Woodstock were accepted as part of Connecticut. In accepting these towns, the General Assembly reasoned that they were granted to Connecticut as part of the colony’s original charter and the 1713 sale was illegitimate because it was in violation of the powers granted in each colony’s charter.

(Copy of Map L from the Massachusetts State Archives as found in The Boundary Disputes of Connecticut by Clarence Winthrop Bowen)

As part of this reversal, Connecticut in theory claimed what is now the southern part of Longmeadow as part of Enfield. In turn, Massachusetts did not recognize that the towns had seceded and continued to include them as part of Massachusetts on official maps, tried to collect taxes, and sent formal notices of feast days and elections. Resolving the disputed area of the border of Longmeadow and Enfield was not resolved until 1797 when commissioners from both states met to settle the issue. At that meeting, Connecticut formally dropped its claim to the area and both states agreed to the present border following the old route of the Longmeadow Brook.

(1794 Map of Longmeadow with text explaining border disputes and historical changes: Credit Longmeadow Historical Society Archives)

Want to learn more about Longmeadow’s borders? Please check out our previous History Note on Longmeadow’s shrinking borders.


Baron, Robert. “Surveying Connecticut’s Borders.” Connecticut Explored 10, no. 2, 2012.

Barrows, Charles Henry The history of Springfield in Massachusetts for the young: being also in some part the history of other towns and cities in the county of Hampden. The Connecticut Valley Historical Society, Springfield, 1911

Bowen, Clarence Winthrop The Boundary Disputes of Connecticut. James R. Osgood and Company, Boston, 1882.

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