In 1729, eleven years after the incorporation of Falmouth (much of which, including the Neck, is now Portland), the selectmen were asked to look for a schoolmaster so the state wouldn’t levy a fine on the town. The law required towns with at least 50 families to employ a qualified schoolmaster to teach their children to read, write, and cipher. For whatever reason, their failure to do so had either not been noticed or had been deliberately overlooked for seven years because the number of families in town reached 50 in 1726, and the Board of Selectmen searched for a proper schoolmaster for four more years after they were asked to act on the matter.
Finally, in 1733, Robert Bailey was hired to serve as Portland’s first schoolmaster. He was instructed to “keep six months upon the Neck, three months at Purpooduck (now South Portland), and three on the north side of Back Cove.”  The following year Schoolmaster Bailey spent two months each at the Neck, Purpooduck, Stroudwater (now Westbrook), Spurwink (now Cape Elizabeth), New Casco (now Falmouth), and Presumpscot (now Portland’s East Deering section). In 1736, Bailey’s salary was increased and a grammar school was established where boys could learn Latin in preparation for college as the law required for towns with 100 or more families. Secondary schools, which emphasized Latin, rhetoric, and advanced arithmetic for boys entering college, were rare outside of the major population centers such as Boston, New York, and Philadelphia.
There is no further mention of Mr. Bailey after 1736 and it is assumed that he was replaced by a Mr. Sewall who kept school on the Neck for six months and was in turn replaced by Mr. Nicholas Hodge, a student at Harvard. When Mr. Hodge graduated from Harvard in 1739, he studied for the ministry under the tutelage of Rev. Thomas Smith, and earned a small income by continuing to serve as Portland’s schoolmaster from 1739 to 1741.
Nicholas Hodge was succeeded by Samuel Stone who kept a school in his home “on the bank of Fore river near the foot of Center street [sic]”. Eventually, Mr. Stone moved to Manchester, Massachusetts, and in 1745, Stephen Longfellow (Harvard 1742), the great-grandfather of Henry Wadsworth Longfellow, came to Portland from York in response to an invitation from Rev. Thomas Smith. According to Portland historian William Willis, the following year Mr. Longfellow had 50 students.
By 1753, Stephen Longfellow and John Wiswell (Harvard 1749) were both schoolmasters on the Neck, but three years later Mr. Wiswell was called to serve as pastor of the Congregationalist Church at New Casco in 1756. In 1764, he traveled to England where he was ordained as an Episcopal minister and returned to Portland in 1765 to serve as pastor of Portland’s newly established Episcopal church. But Mr. Wiswell was a Tory and shortly after the American Revolution began, he took refuge in Boston and later returned to England. After the war, he accepted an offer to serve as pastor of a church in Cornwallis, Nova Scotia.
Peter Smith (Harvard 1753), son of the Rev. Thomas Smith, opened a school on the Neck in 1755, but the following year he moved to Windham. He was succeeded by a Mr. Wallace who kept a schoolhouse on the corner of Middle and School (now Pearl) Streets, where Stephen Longfellow had also taught. Also in 1756, Jonathan Webb (Harvard 1754) came to Portland and soon opened another school on King (now India) Street. He was known to his students as a strict disciplinarian and, when he was well out of ear shot, they called him “pithy Webb” because he had a habit of putting the pith of a quill in his mouth when he cut it. When a young student, Edward Preble, who would later become the distinguished naval commodore, almost broke Schoolmaster Webb of his habit by making the pith of the quill next to be cut very disgustingly distasteful.
Portland’s next schoolmaster, Moses Holt (Harvard 1767), taught but a very few years before he died of consumption (tuberculosis) at age 27. Samuel Freeman (attended Harvard), a former student of Stephen Longfellow and later Judge of Probate for Cumberland County, kept a public school on the Neck in 1764, which became a private school the following year. In 1767,
Theophilus Parsons (Harvard 1769), who was to become the distinguished Chief Justice of the Massachusetts Supreme Court, opened a school on the Neck in 1770. While fulfilling his teaching responsibilities, Parsons read law under Theophilus Bradbury and was admitted to the Cumberland Bar in July of 1774. His school was on King (now India) Street, and later on Back (now Congress) Street. John Frothingham (Harvard 1771) also kept a school here and studied law under Mr. Bradbury with Mr. Parsons. In 1790, John Frothingham would be appointed by U.S. District Court Judge David Sewall to serve as a defense attorney for Thomas Bird and Hans Hanson who were charged in the murder of Captain John Connor. Hanson was acquitted, but Bird has the dubious honor of being the first person to be executed under the authority of the then new U.S. Constitution.