EDITOR'S NOTE: Fairfield, established in 1639, is one of Connecticut's oldest communities. From its settlement 375 years ago by English colonists on "four squares" of land that Native Americans called Uncoway to the vibrant town of 60,000 residents that it is today, Fairfield's history is a chronicle of compelling events and colorful characters.

The Fairfield Citizen will highlight vignettes from that rich history throughout this 375th anniversary year on a regular basis.

The idea of bringing a railroad, a trolley line and then a motor vehicle "parkway" into Fairfield scared some residents from the 1840s right into the 20th century. They feared that outsiders -- undesirable ones, at that -- might ride the rails and roads into town.

The town twice turned down proposals to link Fairfield to neighboring communities and beyond via train, including a proposal by the Housatonic Railroad to build a line from Bridgeport into Fairfield.

But the trains came nonetheless, and by 1849 train trips were made daily from Fairfield and Southport into Manhattan on tracks built by the New York and New Haven Railroad, according to historian Thomas Farnham.

By 1870, six trains arrived daily from New York and six from New Haven, and the fares were nothing like they are today. The fare to ride from Southport to New York was only $1.40 in 1880 and the trip took about two hours.

Today, Fairfield is one of only a handful of towns on Metro-North Railroad's New Haven Line that has three passenger stations.

Despite the rise of steam locomotives on the region's railroads, Fairfield residents still fought extending trolley lines into town for almost another 50 years. But in 1893, several horse-drawn trolley companies merged, and the new company was chartered to build a trolley line in Fairfield.

Citizens fought about the route the trolley should take, writing letters to the editor about a general decline in morality and serenity in town should the trolley run down Old Post Road, then called Main Street. Despite dire predictions, the trolley tracks were laid along the Main Street route. Trolleys continued to run in Fairfield into the next century, finally ending service in 1937.

Controversy over transit erupted again when the Merritt Parkway was proposed and Greenfield Hill residents worked ferociously to limit the parkway's exits and entrances in their neighborhood.

The fight was led by the Greenfield Hill Improvement Society, which continues to this day to lobby for preservation of the leafy neighborhood's character. The Merritt Parkway was opened in 1939 to travel, but Greenfield Hill residents succeeded in blocking a proposed entrance/exit interchange on Redding Road, creating a long stretch of the highway still widely known as "no man's land."

The last major transportation infrastructure added to Fairfield's landscape was the Connecticut Turnpike, now Interstate 95 as part of the federal highway network. The heavily traveled road was opened in 1958 and bisects Fairfield along a route paralleling U.S. Route 1 through town.