Delighting in the Day: The Sunday Drive


Any day is a good day for a road trip, but there is something special about a Sunday drive, typically driving for just the pleasure of it with no particular place to go.

Technology has taken some of the fun out of wandering aimlessly, so we found a plethora of things to do and see as you meander down the chain of lovely country roads that comprise Long Island’s North Fork.

But first, a little history lesson to preclude your drive.

We’re going to go all the way back to 1620 when the Pilgrims landed at Plymouth Rock. Many of the English settlers gradually migrated south to a place called Yennicott. In 1640, a clergyman named Rev. John Youngs was commissioned by the Governor to organize the Yennicott plantation, which he named Southwald. This plantation later became known as Southold and encompassed the area between Orient Point, Riverhead and Wading River.

Southold, Long Island

Southold, Long Island

This year marks Southold’s 375th Anniversary and to celebrate this milestone, there are tons of events planned for your enjoyment, including:

July 6th and 7th
A weekend of activities, including a parade led by L’Hermoine frigate, an exact replica of the tall French ship that brought general Marquis de Lafayette to the United States. For more information go to

At the end of the Long Island Expressway, take a one-lane road to some of the most beautiful scenery in the US. Your first stop is:

Custer Observatory

See the stars at Custer Observatory

Custer Institute and Observatory
You’ll literally be seeing stars at Long Island’s oldest public observatory. Telescopes are set up on the lawn for you to enjoy starry nights, too.
115 Main Bayview Road, Southold, NY 631-765-2626,

Cutchogue Village Green Tours
Take a guided tour of historic buildings ranging from 1649 to 1890. All tours start at the Carriage House, adjacent to the parking area. Admission is free, but donations are welcome.

East End Seaport Museum & Marine Foundation
Explore the rich maritime heritage of the East End, including the Village Blacksmith Shop.
3rd Street, Greenport, 631-477-2100,

Museum Complex, Southold Historical Society

Museum Complex, Southold Historical Society

Southold Historical Society
Twelve buildings make up this complex filled with exhibits that chronicle the history of the area. Check their calendar for special events and more info on their summer program for children. Don’t miss the Horton Point Lighthouse and Nautical Museum, maintained by the Southold Historical Society, an 8-acre park adjacent to the beach and a nature trail.
54325 Main Road, Southold, New York, (631) 765-5500,

Taking a road trip? Share it with us on social. Tweet a photo of you and your Bimmer using #BMWRoadTrip or tell us about your trip on Facebook using #‎BMWRoadTrip.


About Author

Competition BMW of Smithtown

Checkmate Magazine appeals to the competitive side of the BMW driver who views life as a journey, not a destination. Someone who defines success not by winning or losing, but by how one responds to both. Checkmate is the first of its kind, a publication written exclusively for consumers by an automotive dealership.

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