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It’s about two o’clock, and there is a silver and blue diesel train that’s pulling two double decker passenger cars as it rumbles and clatters past the Post Office (Jefferson Store) on Peconic Lane heading eastbound to the seasonal Village of Greenport. This is one of the now daily trips the Long Island Rail Road (LIRR) makes from Riverhead to Greenport. It was once a formidable rail system that carried New York City residents to New England via a ferry in Greenport. The LIRR failed to compete with the New England railroads and soon became a Long Island commuter railroad. The Pennsylvania Railroad in 1900 bought controlling interest for 6 million dollars, hoping to improve commuter service, in the New York area by building the tunnels under the East River and the Hudson. They even built Penn Station to accommodate the passenger service.
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In 1832, long before there was a Statue of Liberty, a private company from Boston formed a predecessor to the LIRR. The Brooklyn and Jamaica Railroad Company (B&J), was the first commuter railroad on Long Island. It was to connect South Ferry, Brooklyn to Jamaica, Queens. A few years later, several investors bought the B&J line and formed the Long Island Railroad Company to transport passengers from New York to Boston via a ferry from Greenport. The tracks finally reached Greenport in 1844 and the travel time from New York to Boston was now down from fifteen hours to eleven. A large device, a turntable, was built in Greenport to turn the train around so it could head back to New York. As opposed to modern diesel trains that use two engines, one to pull east and another at the other end to pull west, steam engines of that time only traveled in one direction and had to be physically turned around. The turntable, although not needed today, can be seen behind the Greenport train station.
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In 1959, the logo of the LIRR was that of ‘Dashing Dan’ symbolizing the commuter nature of the railroad. In 1962 they added ‘Dashing Dottie’ to the company’s logo collection. In 1965, Governor Nelson Rockefeller helped begin the Metropolitan Commuter Transit Authority (MCTA) to modernize the LIRR. The MTA (commuter is gone) owns and operates the LIRR. At present, the familiar MTA logo adorns all the LIRR passenger cars and engines.
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As that silver and blue diesel clatters along, it passes several stations on the way. It also passes places where stations once stood. Alongside the Post Office in Peconic was the LIRR Hermitage station, as Peconic was once called. The building where the Post Office is was once a grocery store, and the station was on the southwest side of the tracks behind the store. That station was closed in 1962. In Cutchogue, there were three stations houses built on Depot Road between the years 1875 and 1962 though none have existed since. The other stations that existed on the North Fork in Jamesport is also long gone. Three train stations on the North Fork still are in service: the Mattituck station, the Southold station, and the Greenport station. With all the changes the LIRR. has gone through, it is still one of the oldest continually used railroad names in the United States.
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Pictured: Cutchogue Train Station from our collection.
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Come view our latest exhibit at the Nautical Museum at Horton Point Lighthouse: ‘Undercover: Stories of Rum Running in Southold.’ The exhibit reveals the characters, unexpected sites and fascinating stories linked to the history of rum running during Prohibition.
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The Nautical Museum is open weekends, 11:30am to 4:00pm, through Sept. 18. We invite you to see the exhibit, explore the rest of the museum and enjoy the beautiful views and scenic grounds. The lighthouse tower will be open most weekends for tours.
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Admission is $5 or $10 for families and includes entrance to the museum, the special exhibit and tower tour.
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Note: Parking is available in the Southold Park District’s lot for a $5 fee (if not a Park District resident). Street parking is by Southold Town Permit only.
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Interested in volunteering to meet and greet visitors at the museum, act as an informal guide or attend the tower? Contact us at: Info@SoutholdHistorical.org or 631-765-5500
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Want to find out about the latest news and events, and view even more historical and posts and videos relating to our rich heritage?
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Please consider following us on our social media channels!
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You can click on the channels to the left and choose ‘Like’ or ‘Follow!’
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Whether you’re searching for a specific item or just hoping to discover unexpected treasure, please join us at Southold Historical Museum’s Annual Yard Sale Sat., June 11 and Sun., June 12, beginning at 8:30 both days. 
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The yard sale will take place on the porch and lawn of the historic Prince Building at 54325 Main Rd., Southold. No early birds please. Cash only. Kindly bring a reusable bag to bring home your finds.
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All proceeds benefit Southold Historical Museum.
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While preregistration is closed, we invite you to join us for our Pickleball Tournament beginning at 9:00am on June 4 (rain date June 5), at Tasker Park in Peconic.
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You can cheer on our community players, learn more about how Pickleball is played, and possibly win a great prize during our raffle.
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Find out why Pickleball, a game that combines aspects of badminton and tennis, is becoming so popular. This fundraising event benefits Southold Historical Museum.
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For further information, please email info@southoldhistorical.org.
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Special thanks to our event sponsors:
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June 4 (Rain Date June 5)
Pickleball Tournament
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June 11 & June 12
Annual Yard Sale beginning each day at 8:30am
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July 1-31
Ten Squared Online Art Exhibit & Sale
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July 2
Maple Lane Complex Reopening
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July 2
Lighthouse Lecture: Stella Prince/Lady Lighthouse Keeper
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July 4
Independence Day Parade Float
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July 9
Lighthouse Lecture: Little Known Aspects of Long Island’s Maritime History
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July 16
Sip of Summer Party
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July 30 & 31
Antiques, Arts & Crafts Fair
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August 6
Ice Cream Social
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AAQ / Resource: Townsend Manor Inn

Old Fashioned Hospitality

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