There is a poll thread that just started similar to this issue, but 1) I promised to start one, and 2) I think a more in-depth discussion is warranted. This is going to be a link-heavy opener.
First: The Electoral College was an invention of the new government in 1793. The population of the "new" United States was 3,929,214 divided into 13 States, and 65 Congressional Districts. The most populous State was Virginia, with 747,610 (but only 110,936 "Free white males", and 292,627 "slaves"). At 17.8 percent, the 1790 Census's
proportion of slaves to the free population was the highest ever recorded by any census.
1790 Census, Wikipedia. In short, the country that created the Electoral College was very different than the one we currently occupy.
Second: At the time of its creation, the President was elected by each State's legislature, not by popular vote. "The Constitution allowed each state to decide how to choose its presidential electors. In 1789, only Pennsylvania and Maryland held elections for this purpose; elsewhere, the state legislatures chose the electors."
Presidential Elections - HISTORY "The 1824 presidential election was the first election in American history in which the popular vote mattered, as 18 [of 25] states chose presidential electors by popular vote in 1824 (six states still left the choice up to their state legislatures)."
United States presidential elections in which the winner lost the popular vote - Wikipedia, and sure enough, the eventual winner, John Quincy Adams,
did not win the popular vote (Andrew Jackson got the most votes). Instead, Adams was elected by the House of Representatives with "Representatives from 13 out of 25 states voting in his favor."
Third: "The Electoral College and its procedure are established in the U.S. Constitution by Article II, Section 1, Clauses 2 and 4; and the Twelfth Amendment (which replaced Clause 3 after its ratification in 1804). Under Clause 2, each of the states casts as many electoral votes as the total number of its Senators and Representatives in Congress, while, per the Twenty-third Amendment ratified in 1961, Washington, D.C. casts the same number of electoral votes as the least-represented state, which is three. Also under Clause 2, the manner for choosing electors is determined by each state legislature, not directly by the federal government. Many state legislatures previously selected their electors directly, but over time all of them switched to using the popular vote to help determine electors, which persists today. "
Wikipedia
Fourth: "Presidential elections occur quadrennially with registered voters casting their ballots on Election Day, which since 1845 has been the first Tuesday after November 1. This date coincides with the general elections of various other federal, state, and local races; since local governments are responsible for managing elections, these races typically all appear on one ballot. The Electoral College electors then formally cast their electoral votes on the first Monday after December 12 at their respective state capitals."