The society was founded by nine prominent men of Romney with the objectives of advancing literature and science, purchasing and maintaining a library, and improving educational opportunities.

The society debated an extensive range of scientific and social topics, often violating its own rules which banned religious and political subjects.

Even though its membership was relatively small, its debates and activities were frequently discussed throughout the Potomac Highlands region, and the organization greatly influenced trends of thought in the Romney community and surrounding areas.

The society's library began in 1819 with the acquisition of two books; by 1861, it had grown to contain approximately 3,000 volumes on subjects such as literature, science, history, and art.

In 1820, as a result of this initiative, the teaching of the classics was introduced into the curriculum of Romney Academy, thus making the institution the first school of higher education in the Eastern Panhandle.

[1][6][7] According to historian Hu Maxwell, these men elected Kuykendall as chairman and Magill as secretary of a committee which was charged with the drafting of a constitution for the society.

[7] Following each meeting's business session, a debate or other literary exercises were to be held consisting of topics of general interest of the members.

[8][10] The society's next meeting was held on February 13, 1819, in the old Hampshire County Courthouse, where the first matter for debate was "Resolved: That a representative should be governed by instructions from his constituents.

[8][10] The second meeting, which was held on February 19 of that year at the Romney Academy, debated the question, "Is an education acquired at the public school or [is] a private tutor to be preferred?"

[11] The debate took place before the construction of the Chesapeake and Ohio Canal along the Maryland shore of the Potomac River to the north of Hampshire County.

[1][12][14] Even though the Romney Literary Society's membership was relatively small, its debates and activities were frequently discussed throughout the Potomac Highlands region.

[12] In order to fulfill one of its primary purposes of establishing a library for its members, the Romney Literary Society gradually began to acquire volumes for such a use.

[10][14] The society's library began with the April 23, 1819, appropriation for the purchase of two books: Plutarch's Parallel Lives and Emer de Vattel's The Law of Nations.

"[11] Within the span of ten years, the society's small library grew to contain approximately 3,000 volumes on literature, science, history, and art.

[10][14] According to the Federal Writers' Project in their Historic Romney 1762–1937 (1937), the book selections and their acquisition "indicate that these men possessed real literary judgment and business ability.

"[14][16] In 1820, as a result of this initiative, the teaching of the classics was introduced into the curriculum of Romney Academy, thus making the institution the first school of higher education in the Eastern Panhandle.

[14][16] Under the guidance, leadership, and strict discipline of Dr. Henry Johnston, Romney Academy became widely renowned for its courses in "higher classics.

"[6][14][16] His successor and society member William Henry Foote introduced courses in theology, and the school's enrollment grew to include students preparing for ministry.

[19][20][21] Following a ten-year lapse, the society made arrangements with James Gregory of Jersey City and Daniel McIntyre of Philadelphia to finance a lottery "for raising a sum of money not exceeding twenty thousand dollars, for the purpose of erecting a suitable building for their accommodation, the purchase of library and Philosophical apparatus.

[20] On February 12, 1844, the Virginia General Assembly passed an act authorizing the society to denote the balance of the moneys raised by the lottery to the Romney Academy.

[15] Following its move to the new building, the academy was reorganized as the Romney Classical Institute and its activities fell under the supervision of the society.

[19][21][24] Foote differed with the society over these matters, and he ultimately declined to accept the new bylaws and resigned his leadership position in October 1849; in 1850, he established a rival institution known as the Potomac Seminary.

[15] After 1853, the society possessed a permanent fund of $12,000, which yielded $720 per year, one half of which was devoted to the support of the Romney Classical Institute.

[24] Among the new members elected between 1869 and 1886 were John Collins Covell, Samuel Lightfoot Flournoy, Henry Bell Gilkeson, Howard Hille Johnson, and Christian Streit White.

[30] Between 1869 and 1870, the society completed construction of a new two-story brick building on Lot 56 at the corner of West Main and North High Streets known as Literary Hall, where it could hold its meetings and reassemble the remaining volumes from its original library.

[28][29] On April 12, 1870, the society passed a resolution by which the members agreed to deed, free of cost, the buildings and grounds of the Romney Classical Institute.

[31] On April 20, 1870, the society sent Andrew Wodrow Kercheval and Robert White as representatives to the then-state capital Wheeling to present their formal offer of "the grounds and buildings of the Romney Classical Institute... to the Board of Regents, free of debt, and in good repair" on the condition that the proposed school be located in Romney.

[29][31][35] It was discovered by the society that in order to follow through with their proposition, it was necessary to raise more than $1,000, which was ostensibly a difficult task during the Reconstruction Era in Romney.

[29][36] To make good on its offer, the society also made an appropriation of $320 on July 11 for the purpose of repairing and restoring the former Romney Classical Institute and grounds so that they were satisfactory before they were transferred to the regents.

[30][38] According to Maxwell, without the efforts of the society, the West Virginia Schools for the Deaf and Blind could not have been secured for Romney, and would have likely been located elsewhere in the state.