During the first half of the 19th century, the town of Strasburg would be altered by the creation of the Pennsylvania transportation system. Strasburg would also play a key role in development of the public school system.

In the early 1800's, Strasburg grew to have as many as 10 taverns- ordinaries as they were called- who shared the company of those who traveled on the Conestoga Road. The Lancaster Turnpike was the first toll-road in Pennsylvania, a preferred method of travel for horse-drawn carriages and coaches, and the first to be macadamized (by John McAdam). Travelers could escape the cost of paying the toll by traveling westward via the inferior Conestoga Road. This event supplied Strasburg with primarily wagon traffic and drovers (cattle dealers). Those that journeyed the Conestoga Road were accustomed to doing so, and frequently requested ordinary services in Strasburg.

In 1816, the town became incorporated and passed an ordinance posing a $3 fine on those "who shall run any horse or horses through the streets, lanes, or alleys of the borough". This event marked the birth of Strasburg's town legislature, which represented a prominent set of constituents.

While the small colony of Strasburg residents would advance the unique Strasburg Rail-Road project through State legislature, they would also foster a public school movement that would lend far-reaching credibility to the town.

Spurred by Nathanial Sample's academic enterprise in the late 1790's, six schools would emerge within Strasburg in the first half of the 19th century. One of these schools, The Strasburg Academy, would gain a reputation as being one of the best academies in the country for both boarding and day students, attracting students from as far away as Cuba and Puerto Rico. It was also during this time in Strasburg's history that resident Thomas Henry Burrowes (The Founder of Pennsylvania's Public School System) was drafting the Normal School law, which was regarded as being unsurpassed by any legislation on this subject either in America or Europe.

In 1902, a trolley line was commissioned that transported travelers from Gap to Lancaster with a stop in Strasburg. A new Post Office was built, and a symbolic spring-fed fountain was constructed in center square.