St. James church is the oldest parish in Western Massachusetts. Occasional services were held here by visiting priests at least as early as 1760. The parish was formally organized on September 21, 1762.

Two years later, the parish built the first Anglican church in Western Massachusetts. Roger Viets, a priest of The Society for the Propagation of the Gospel in Foreign Parts, described it in a letter dated March 14, 1764: "The people in Great Barrington have actually begun to provide materials for erecting a church, which is to be by far the most beautiful and expensive building in that country." A prosperous Dutch farmer, John Burghardt, deeded a quarter acre of land south of where the present church is. Others gave lumber or money. Volunteers used the floor plan of Christ Church, Stratford, the oldest Anglican parish in Connecticut, to design the church. A ship's bell, which was the first church bell in town, was given by a well-wisher and hung in the belfry. The window panes from England, a gift of Lord Barrington (William Pitt's war minister) were used so freely and the windows made so large, that the church was called the "Glass House". Lord Barrington was said to have been annoyed when he received the unexpectedly large bill.

The first service was held in the church on Christmas Day, 1764, and was the first such observance in Puritan Berkshire County. Even though the Massachusetts Charter of 1691 guaranteed religious freedom, there was opposition to the founding of an Anglican parish. Visiting SPG priests were harassed and actually arrested in the early years of St. James.

The church's first rector was Gideon Bostwick. His ministry began in 1760 and lasted 23 years. During that time, remarkably, he was missionary to 47 towns, traveling on horseback throughout Vermont, New York, and Massachusetts. Another clergyman of note caused the parish to become one of the first in this diocese to go "high church". In 1885 the Holy Eucharist became a part of the regular Sunday and Holy Day service as is the custom today. Candles on the altar and Eucharistic vestments were introduced in 1902.

Although built in 1764, the church was not consecrated until 1823. Ten years later it was replaced by a small stone church near the center of Great Barrington. When that building was outgrown, a new site was purchased next to Town Hall. A large stone gothic church was built in 1857 at a cost of $15,232. The stained glass windows dating from the late 19th and early 20th centuries have been restored to their original splendor. The parish hall was added in 1911.