![]() Although primarily a stationery store, Weintraub’s also offered toys, candy, cigarettes, magazines, and novelty gifts. Trackside Smoke Shop and J’s Natural Market: Originally a news stand operated by Abe Weinstock in the 1920’s and 30’s, Weintraub’s Stationers was one of downtown Syosset’s most beloved variety stores for almost forty years. The Station Diner took its fondness for railroad travelers over the top with a working model railroad that zipped around the counter area all day long! Dunkin’ Donuts: Formerly the Syosset Station Diner, a friendly gathering place for morning commuters of the 1950’s and 60’s. Designed as a welcoming gateway that signifies home, recreation, and the area’s natural attractions, the colorful sail casts a kaleidoscope of colorful shadows all day long. The 21’ tall stainless steel and plexiglass sculpture that adorns the front of the current station is the work of Brooklyn-based artist, Tom Fruin. Additional renovations were made in the early 1990’s, again in the early 2000’s, and then in 2018-2019, when the LIRR demolished virtually the entire station house and replaced it with the modern structure that stands today. In 1960, the LIRR built an overpass at the east end of the station to accommodate the rapidly increasing number of commuters. The original station received its first major overhaul in 1948, when the entire wooden façade was refinished in brick. Other local celebrities who traveled in and out of this station over the years include music legend Billy Joel, Broadway star Idina Menzel, and movie actress Natalie Portman. One of the most famous early commuters at this station was the 26 th President of the United States, Theodore Roosevelt, who often used the station when traveling back and forth to his “Summer White House” in Oyster Bay. The station initially had a crossing guard to stop horse and wagon traffic on Jackson Avenue when a train passed through, but added manually operated crossing gates in the early 1900’s and electric gates in 1952. In its early days, this station received the hamlet’s mail, as well as telegraph messages sent via Western Union. The first Syosset station house (shown above) was moved here from an under-utilized station in Far Rockaway in 1877 and rested on the same foundation as today’s ticket office and waiting room. Soon after, hotels, saloons, and stage coach services sprang up in the area and Syosset was on its way to becoming a booming suburb. When plans to build a branch off the main railroad line from Hicksville to the whaling port of Cold Spring Harbor stalled halfway through, Syosset became the end of the line and, subsequently, a transportation “hub” for all surrounding North Shore villages. Before the railroad came to town, Syosset was a sleepy farming community of fewer than 200 residents. Please proceed with caution and at your own risk.Įstablished in 1854, the railroad station on Jackson Avenue is where modern-day Syosset began. ![]() Please note that this historical walk is not officially endorsed by the Syosset Woodbury Chamber of Commerce and that neither the Chamber nor the author make any representations as to the safety of walking the streets, sidewalks, and crossings of downtown Syosset, either on the day of the street fair or on any other day. The descriptions of each location have been edited down to the basics to keep the length of your walk reasonable, but you will likely want to learn more when you are finished with the tour. ![]() From there, you will head north, through the fair, stopping at various shops and other landmarks along the way to learn a little about the businesses that lined Syosset’s downtown streets in the 19 th and 20 th Centuries. The suggested starting point is at the stained glass “Sail” sculpture in front of the LIRR station, on the north side of the tracks. The walk covers a little more than half-a-mile and stays within the fair zone, for the most part. If you’ve been thinking about exploring the history of the downtown area, the day of the fair is a good time to gather your family and take this quick self-guided historical walking tour, prepared by Tom Montalbano, lifelong Syosset resident and author of several books about the Syosset-Woodbury area. The Syosset Woodbury Chamber of Commerce Street Fair provides a rare opportunity to get out and see downtown Syosset without the stress and safety concerns of Jackson Avenue’s sometimes overwhelming automobile traffic.
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