[2] Two companies that later formed part of Penn National Gaming were founded in 1968 by groups seeking one of the four available racing licenses: Pitt Park Raceway, Inc., formed by several Erie area businessmen,[3][4] and the Pennsylvania National Turf Club, established by a group of Central Pennsylvania investors.

[13] Pitt Park lost half a million dollars in its first meet, leading its owners to sell the company to a group of investors, including Philadelphia insurance businessman Peter D.

[19][20] The Turf Club continued to operate its own racing meet each year, now as a tenant of Carlino.

[21] PNRC Corp., which had been incorporated in 1982, was renamed as Penn National Gaming, with Mountainview and the Turf Club as its subsidiaries.

[25][26] Penn National expanded beyond its first racetrack with the acquisitions of Pocono Downs in 1996, Charles Town Races in 1997, and, in 1999, a half interest in Freehold Raceway and the operations of Garden State Park.

[27] Penn National also won approval to begin offering slot machines at Charles Town in 1997.

[35][36] The purchase again doubled Penn National's size, making it, at the time, the third largest publicly held gaming company in the country (behind MGM Mirage and Harrah's Entertainment).

[39] An attempt in 2007 to take the company private with a $6.1 billion buyout fell through for prospective buyers Fortress Investment Group and Centerbridge Partners.

[52][53] To ensure regulatory approval for the deal, Pinnacle sold four of its properties to Boyd Gaming prior to the merger.

In connection with the sale, Penn National sold the real estate of Plainridge Park Casino to GLPI for $250 million.

[56][57] In July 2019, Penn reached market access agreements with multiple gaming companies, including DraftKings, PointsBet, theScore, and The Stars Group, which would allow the companies to sub-license "skins" allotted to land-based casinos owned by Penn for offering iGaming and sports betting in their respective states.

[70] The company subsequently announced a sponsorship agreement between theScore and the Toronto Blue Jays as its "official gaming partner".

To license the branding, Penn would pay $1.5 billion in cash, and give ESPN options for $500,000 of its stock.