Cutter's parentage is not clear, but he was a descendant of the Haviland family and later inherited or bought much of their land. He had a limited education, mainly from reading the bible. He catapulted into high society by marrying a daughter of the well-propertied Allen family of Great Neck, NY. He later acquired the Allen mill, which thereafter was called Cutter's Mill (and after which Cutter Mill Road in Great Neck is named). His main occupation was farming, but Cutter also became quite a propertied landowner, eventually owning numerous parcels in Great Neck as well as large blocks of land north of the railroad station there, and across Manhasset Bay in Plandome Heights, New York, where he lived towards the end of his life. During the course of his business dealings he developed a reputation for honesty and sound business acumen.
Cutter also developed a reputation for being a "character." Perhaps it was his old-fashioned clothes, his country accent, or the poetry ("doggerel" is what some more properly called) that he wrote and distributed. His reputation was sealed when in 1867 he booked passage for a 5-month trip to the Holy Land. Mark Twain turned out to be one of the passengers, and Cutter found himself immortalized in Twain's book Innocents Abroad as the character the "Poet Lariat." This is how Mark Twain described Cutter in his notes for the book:
- He is 50 years old, and small for his age. He dresses in homespun, and is a simple minded, honest, old-fashioned farmer with a strange proclivity for writing rhymes. He writes them on all possible subjects and gets them printed on slips of paper with his portrait at the head. These he will give to any man that comes along, whether he has anything against him or not.
For the rest of his life Cutter relished being referred to as the "farmer-poet" or the "Poet Lariat" and told of his acquaintance with Mark Twain to anyone he met. In 1886 his work was collected in a 500-page book titled The Long Island Farmer's Poems.
Cutter died in 1906 at the age of 89. A tall granite gravestone marks his burial site in the Zion Episcopal Church cemetery in Douglaston, Queens. Most of his estate, valued at over $500,000, was willed to the American Bible Society, including the lands which became the Incorporated Village of Plandome Heights. His huge collection of books and antique furniture was sold at auction.
- "Poetical lecture, suggested after seeing the model of Solomon's temple". March 5, 1860. L.I. Times Office. 1860. 20 pages
- "A poem on the New England kitchen" Little Neck, L.I. 1864. 8 pages.
- "Lines on the Egyptian obelisk 'Cleopatra's Needle'. Bloodgood W. R. Burling, Printer. 1881. 8 pages
- "The Long Island farmer's poems" New York. N. Tibbals & sons (published for the author). 1886
- Grimes, William (11 August 1995). "A Poet Without Honor in His Own County; Queens's Answer to Whitman Never Attained the Eminence of Brooklyn's Bard". The New York Times.
- Jackson, edited by Kenneth T.; Keller, Lisa; Flood, Nancy (1995). The encyclopedia of New York City. New Haven: Yale University Press. ISBN 0300055366.