At the turn of the 20th century, business was booming at the Winchester Arms Factory. Its owner, Oliver Winchester, came to the business from a background in high-end clothing, but the firearms business would prove his great success. The plant here on Munson Street was built in 1871; Winchester chose the location in part due to its proximity to the railroad for ease of receiving raw materials and shipping product. By 1900, Winchester was among the the top three arms manufacturers in the United States, and its products were being sold as far away as Russia and China. Public figures such as John Wayne, Teddy Roosevelt, Ernest Hemingway, and Annie Oakley favored the Winchester rifle, which had become an icon as “The Gun That Won The West.” At its peak, Winchester Arms was to become the largest employer in the city, boasting a workforce of nearly 20,000 on its sprawling campus.

Many of these factory workers made their daily commute using New Haven’s extensive streetcar system, which started out as a handful of horse-drawn cars on rails and quickly turned into a sprawling network of over 500 electrified trolleys. The cars connected the neighborhoods of New Haven via main arteries, including Winchester Ave, Whalley Ave, Grand Ave, Edgewood Ave, and Chapel St. They also linked New Haven to surrounding towns, joining up with other lines in the network. By the turn of the century, a passenger could travel 194 miles of the 246-mile route from New York to Boston entirely by trolley.