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This collection contains nineteen letters sent to Carlton Heath and one letter sent to Ruth Heath between 1828 and 1854. The bulk of the letters were written by Amos and Emily Pilsbury of Weathersfield, Connecticut, mostly from the Connecticut State Prison where Amos Pilsbury worked as deputy warden and warden. Amos Pilsbury discussed prison management and provided glimpses into prisoners' experiences. He wrote frankly about his political and ideological disputes with his brother-in-law, opposing his positions on the Whig party and abolitionism. Amos Pilsbury commented on his religious practices and beliefs, family news, Thanksgiving celebrations and meals, and disgruntlement over the Heath family's failures to write and visit. Five additional members of the extended Heath family wrote portions or entire letters present in the collection, mostly weighing in on family news.

This collection contains nineteen letters sent to Carlton Heath and one letter sent to Ruth Heath between 1828 and 1854. The bulk of the letters were written by Amos and Emily Pilsbury of Weathersfield, Connecticut, mostly from the Connecticut State Prison, where Amos Pilsbury worked as deputy warden and warden. Amos Pilsbury discussed prison management and provided glimpses into prisoners' experiences. He wrote frankly about his political and ideological disputes with his brother-in-law, opposing his positions on the Whig party and abolitionism. Amos Pilsbury commented on his religious practices and beliefs, family news, Thanksgiving celebrations and meals, and disgruntlement over the Heath family's failures to write and visit. Five additional members of the extended Heath family wrote portions or entire letters present in the collection, mostly weighing in on family news.

Amos Pilsbury's letters include references to his work in prison management, with detailed descriptions of religious services in the Connecticut State Prison (April 28, 1829) and various projects contracting out the labor of imprisoned people, including for the production of shoes (November 9, 1828), rifle pistols (November 24, 1837), and cane chairs (February 18, 1842). One letter was written during Pilsbury's tenure at the Albany penitentiary, where he lamented a business being lost to fire as it impacted his ability to dispose of a large order of chair seats (August 30, 1854). In several letters, Pilsbury commented on prison discipline, African American prisoners (April 28, 1829; June 20, 1836; February 18, 1842), and the high demands wardenship placed on him.

Several of Pilsbury's letters indicate the challenges political and interpersonal conflict posed for him as a prison warden at Weathersfield. He wrote on February 20, 1832, of the "Powerful efforts [that] have been made to injure me, and destroy publick confidence in the administration of the affairs of the Prison," preceding his removal from office based on accusations of misconduct by Connecticut politician Martin Welles. He wrote again on July 27, 1833, acknowledging his reinstatement, anxiety about returning, and the decline in discipline at the Connecticut State Prison during his absence. Reflecting further on the incident on December 9, 1833, he mused, "How things have changed in one short year? At that time I was spending my time in idleness having been 'reformed' out of office. At that time no report had been made concerning things charged upon me by a personal enemy and persecutor." Following a Whig victory, Pilsbury acknowledged the possibility of political shifts impacting his employment, writing, "as I was before the election, so I am now, & trust I ever shall be, a Democrat. You ask 'wheter we expect to be removed & when?' In answer I can only say, that the Whigs have the power to remove me, whether they will or not remains to be seen" (April 21, 1838).

Amos Pilsbury and Carlton Heath appeared to have had a fraught relationship, and Amos's letters reveal frustration with Heath's failure to write and visit as well as strong opposition to Heath's support of Whig politics and abolition. Amos Pilsbury acknowledged his conviction of African American inferiority, the impossibility of immediate abolition, and the impropriety of New Englanders weighing in on slavery (June 20, 1836; April 21, 1838; September 4, 1838). One relative even joked that Pilsbury's opinions had changed. "They now wish to have all former difficulties which have arisen between you in consequence of not agreeing in Party feelings put an end to … Do excuse my sad mistake ... It must be I did not look at the right words in the Dictionary… it is the reverse" (March 1, 1841). Tensions between these family members based on strongly felt political and ideological positions appear throughout the letters.

Five additional members of the extended Heath family wrote portions or entire letters present in the collection, mostly weighing in on family news, visiting Weathersfield, and disagreeing about the duration of Ruth Heath's stays with the Pilsbury family.