To get from New York to Portland, Oregon by water you could go south and then west through the Straits of Magellan. Alternatively, you could go east around the globe until you reached Portland.

1. Thomas Walker explores Kentucky through the Cumberland Gap
2. Louisville and Portland Canal opened.

The Panama canal connect the Atlantic and the Pacific Oceans.

If there was no canal a ship would have to travel all the way around the southern tip of South America.

The Caribbean Sea and the North Pacific Ocean are connected by the Panama Canal.

Prior to its' construction, ships traveling from New York to Portland Oregon would have to sail ALL THE AWAY AROUND South America. This is known in sailing parlance as "rounding the Horn", because Cape Horn is at the southern tip of South America.

There is a Portland, Oregon and a Portland, Maine.