The Ebenezer Bolles family papers relate to Ebenezer Bolles (1764-1826), his sons Ebenezer W. Bolles (1793-1854), Samuel Penfield Bolles (1795-1875), and Henry Bolles (1802-1849), and Samuel's wife's half-brother William Mather Clark (1805-1878). The papers consist of correspondence, deeds, legal papers, and account books. Ebenezer Bolles (1764-1826) married Abigail Penfield Bolles (1763-1844). They settled in Litchfield, where all of their children where born; as adults, most of them moved elsewhere. Ebenezer had a saddle and leather business. The papers contain two documents relating to young men who apprenticed with him and deeds that record his land transactions. Sons Ebenezer W., Samuel, and Henry were merchants. Their correspondence documents their less-than-successful ventures in cities in the southern United States during the early 1820s. Ebenezer W. and Samuel returned to Litchfield. Ebenezer continued in his father's business, the activities of which are documented in several account books, 1820s-1840s. There are also two letters to Samuel from Mary S. Bradley (1780- ), the daughter of his grandfather's second wife. Samuel married Roxana Clark Bolles (1803-1892) of Litchfield. The papers contain several letters written during the 1820s by her half-brother William Mather Clark to his parents, Stephen Clark and Roxana Phelps Clark of Litchfield and sisters Roxana and Sarah.