Longmeadow was first settled in 1644, and officially incorporated on October 17, 1783. The town was originally farmland within the limits of Springfield. It remained relatively pastoral until the street railway was built circa 1910, when the population tripled over a fifteen-year period. After Interstate 91 was built in the wetlands on the west side of town, population tripled again between 1960 and 1975.

During the 19th and early 20th centuries, Longmeadow was best known as the site from which Longmeadow brownstone was mined. Several famous American buildings, including Princeton University's Neo-Gothic library, are made of Longmeadow brownstone. In 1894, the more populous and industrialized "East Village" portion of the town containing the brownstone quarries split off to become East Longmeadow.

Designed by famed golf course architect Donald Ross in 1922, the Longmeadow Country Club was the proving ground for golf equipment designed and manufactured by the Spalding Co. of Chicopee. Bobby Jones, a consultant for Spalding, was a member in standing at LCC and made a number of his instructional films at LCC in the 1930s.

Longmeadow is located in the western part of the state, just south of the city of Springfield, and is bordered on the west by the Connecticut River and Agawam, to the east by East Longmeadow, and to the south by Enfield, Connecticut. It extends approximately 3 miles (5 km) north to south and 2.5 miles (4.0 km) east to west. It is approximately 20 miles (32 km) north of Hartford.

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