The shipbuilding activity that followed marks the true genesis of Summerside, and it was the entrepreneurial brilliance of one man, Joseph Pope, which made the community a shipbuilding centre. After building a few vessels in their shipyard at Bedeque, inadequate drought forced Pope and his son, James Colledge, to move across the bay to Green’s Shore where vessels of medium to large tonnage could safely be launched. The senior Pope’s wealth and political prominence soon led to improvements to road communications with the village.

In 1851, on the eve of colonial responsible government, Summerside was rapidly becoming a trading centre. New immigrants as well as tradesmen and merchants from the longer settled areas of Bedeque, Malpeque and St. Eleanors moved into “town” in search of employment. The export trade in timber and agriculture produce was thriving and regular steam communication had been established with other colonial ports. A wagon path known as “Broadway” (Water Street) now extended east along the shore to meet the western post road.

Joining the Popes in shipbuilding were John Lefurgey, James Ramsey, Angus McMillan, James Muirhead, together with a host of tradesmen and mariners and a few merchants who dabbled in the construction of wooden sailing vessels. One of the latter group, Robert T. Holman, did more than dabble in both mercantilism and shipbuilding. Holman had come to Summerside indirectly from Saint John, New Brunswick and was a man of immense ability and energy. His business in produce and retailing eventually became the largest and most successful of its kind in the colony. Mr. Holman had no equal in the county as a man of example and influence, though he never took an active role in political life.

Summerside in the 1860’s was at the zenith of its affluence, a community totally consumed with planking decks, shipping oats and potatoes, and simply “doing business.” Although decidedly maritime in character; that is, with one eye seaward, the town had also developed a keen appreciation for and dependence on the labors of the farmer. For it was the farmers’ produce and patronizing of local retailers which stabilized Summerside’s economy and would sustain it long after the subsidence of shipbuilding. The town came alive at market time. Carts filled with produce lined Water Street on their way to the schooners, while storekeepers manned their posts at daybreak hoping to catch some business from a ploughman just compensated for his crop. Crabbe’s Hotel, a favourite stopover spot for members of the agricultural class, was usually full to capacity.

A preoccupation with business precluded for a time necessary initiatives in civic organization and public welfare. Meandering cows were left to determine the direction of streets, inadequate water supply threatened townspeople with disease and fire, and paupers frequented the doorways of the well to do. Nevertheless, Summerside did make significant strides in civic improvement over the next decade Limited powers conferred by an 1875 incorporation of the community, under the Provincial “Towns and Villages Act,” were extended in April 1877 when Summerside assumed full corporate status. The Incorporation Act of 1877 was comprehensive and gave the Wardens of the Town rights of taxation previously held by the Province.