Founded in 1721 Litchfield was designated the county seat in 1751, and by the1790's the town had become the leading commercial, social, cultural and legal center of Northwestern Connecticut. Its population grew from 1,366 in 1756 to 2,544 in 1774, and by 1810 Litchfield was the fourth largest settlement in the state with a population of 4,639.

Unlike many Connecticut towns, Litchfield prospered during the Revolution. While Connecticut's coastal and river towns were under constant attack by British forces, and while New York City was occupied by the British, Litchfield became a major "safe town" of the Continental forces. The main roads from Hartford and Southern Connecticut to the Hudson Valley ran through Litchfield and most of the provisions and munitions for the Continental Army beyond the Hudson followed this route. Litchfield became a chief depot for military stores and a safe place to jail Loyalist prisoners.

The fifty years between 1784 and 1834 are known as Litchfield's "Golden Age". During these years, the town was an active, growing urban center. Local merchants made fortunes in the China trade, small industries were developed, and by 1810 the central village contained 125 houses, shops and public buildings. The town had an active artisan community with goldsmiths, carpenters, hatters, carriage makers, joiners, cabinet makers, saddlers, blacksmiths, potters and other craftsmen all located within the central village.

Beginning in 1784, Litchfield lawyer, Tapping Reeve, systematized his law lectures for young students, creating the Litchfield Law School. Reeve was the first to develop a series of formal, regular lectures that insured that all students had access to the same body of knowledge. The lectures became so popular that in 1784 Reeve built a small school building adjacent to his house to accommodate his growing classes, and to house his law library. Over its 60 year history, more than 1,500 men graduated from the Litchfield Law School, many of them going on to distinguished careers. The list of graduates includes two Vice Presidents, Aaron Burr and John C. Calhoun, over 100 members of the House of Representatives, 28 senators, 14 governors, 14 cabinet members, 34 State Supreme Court Justices, and 3 Justices of the United States Supreme Court.

Established in 1792, Sarah Pierce's Litchfield Female Academy was one of the first major educational institutions for women in the United States. Over its forty-one year history the school enrolled more than 2,000 students, established a national reputation, and evolved a highly challenging academic curriculum. The school was an institution in transition, begun as a typical small select or private school which offered a simple course of academic and ornamental subjects taught by single teacher, later becoming a large female academy with a full staff of teachers and an academic curriculum rivaling the best schools of the period.

During its "Golden Age" Litchfield had an unusual number of college educated inhabitants. In 1791 Samuel Miles Hopkins, a student at the Litchfield Law School, described Litchfield in his journal as a town of "hard, active, reading, thinking, intelligent men who may probably be set forth as a pattern of the finest community on earth ".

The Reverend Dan Huntington, a Congregational minister in the town from 1798 to 1809, wrote upon his arrival in Litchfield:

"A delightful village on a fruitful hill, richly endowed with schools both professional and scientific, with its venerable governors and judges, with its learned lawyers, and senators both in the national and state departments and with a population both enlightened and respectable, Litchfield was now in its glory".

Litchfield's fortunes declined during the later years of the nineteenth century. The town did not have the ample water supply and rail transportation necessary to establish industry and the village became a sleepy backwater. Rediscovered as a resort community in the late nineteenth century Litchfield became a popular spot for vacation, weekend and summer homes. The town embraced the Colonial Revival movement and by the early Century many of the homes began to sport the white paint and black shutters we see today.