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The view from Westmoreland. (Credit: Al Collard)

Westmoreland offers a walk that’s modestly challenging, about a mile long, picturesque and full of history. 

Westmoreland Drive is a public road, coursing through the area that was at one time all known as Westmoreland. Today, the center of the area is Westmoreland Farm, privately owned by the Roe family.

Although not open to the public, the farm contains iconic landmarks that are easily visible from the road. The farm radiates from an old clock and water tower, built in 1900 by the estate’s original owner, Thomas M. Turner.



Access: This is a public road, but bordering properties are private.

Length: 1 mile, almost all flat.

Highlights: Historic farm, estate and buildings.

When it was built, it was the tallest structure on the Island, and probably in Suffolk County. Turner’s Italian sunken garden, filled with Italian marble statuary, is kept neat, but allowed to show its age, only enhancing its enigmatic beauty.


Walking down the road, you’ll pass quiet pastures, a stunning allee of linden trees lining the road into the farm, and four horses who are usually out in the field. They are a treat for children to observe up close. Their owner, Karen Roe, only requests that visitors don’t feed them, since they need to adhere to an appropriate diet. Across from the horse pasture, a long swath of lawn stretches almost to where Westmoreland meets West Neck Creek. 

The Roe family owns this land, once an airstrip, but has sold its development rights to ensure houses won’t be built on it. They have dedicated it to James and Margaret Roe, the patriarch and matriarch of the family, who at one time owned all of Westmoreland. In 1967, when James Roe was a powerful Democratic leader, Sen. Robert F. Kennedy and his wife Ethel flew to Shelter Island and landed in Westmoreland, where the Roes hosted a barbecue in their honor, as was their custom, with many children enjoying hayrides around the farm.

The fountain at Westmoreland. (Credit: Ambrose Clancy)


As I walk down the road, one of my favorite houses has always been the Primrose, a Tudor that looks like it was dropped in from another era. It was built by Turner as a mansion for himself and his wife. He was a close friend of Broadway producer Charles Frohman, actress Maude Adams and Scottish playwright J.M. Barrie, who visited Shelter Island and wrote his play “Peter Pan” with Ms. Adams in mind. The play was already a hit in London with its British cast in the summer of 1905 when rehearsals were underway to open it on Broadway, with Ms. Adams as Peter. 

Turner offered his Shelter Island estate for an outdoor rehearsal, bringing in contractors, electricians and mechanics to mount a production of “Peter Pan” on the grounds. Wire was strung from the tower to the roof of the cow barn to enable the actors to “fly.” 

The waters of West Neck Bay and nearby ponds were perfect lagoons for the play’s island setting, and it’s easy to picture child actors swinging from the branches of the lindens and chasing each other across the grass, so much more naturally than onstage. Islanders were all welcome, along with many out-of-town guests who filled the Island’s hotels and guest houses. The one-time “rehearsal” went off successfully, and was celebrated with a feast afterward. 

Thereafter, Turner referred to the estate as Never Never Land, which is the title of a wonderful book by Frances Roe Kestler.

This book on Westmoreland is full of details about all of Shelter Island’s history as well as recollections about the Roes and all the other families who came to buy surrounding properties, houses with names like “Osprey,” Overlook,” and “Hawthorne.” 

A bird’s eye view over Westmoreland. (Credit: Jim Colligan)


Westmoreland, like any neighborhood, became a network of families who were very close. Over the years, as friends passed away or moved on, it’s been difficult to avoid a sense of sadness as I walk past their homes. I still feel touched by their spirits. Frances Kestler quotes J.M. Barrie as saying, “ The finest dream in the world is … when everyone I have loved is still alive.” 

The antidote to melancholy is rounding the curve on the road, meeting the new neighbor children who are selling friendship bracelets. As I select my bracelet, I happily learn that this family now lives in a Westmoreland house where my close friends grew up. Life goes on.

The walk up and down Westmoreland Drive is just about a mile, and virtually flat except for one hill sloping down next to a pond near the entrance to Westmoreland. We all call the entrance the gate, although we don’t remember an actual gate ever being there. 

If you want to challenge yourself a bit, turn left out of the gate and continue on West Neck Road, up a hill and around a bend. Cross the Nostrand/Brander Parkway intersection and continue down the length of Bootleggers Alley. This short lane, whose name alludes to the Island’s prohibition era enterprises, offers the reward as you reach the end. You may be feeling the cold by then, but it’s worth it. 

At the end of the lane, a panoramic view of Peconic Bay spreads before you. And it is not unusual to have the entire vista to yourself. Bend down and run your hands through the water and pick up a shell or two, just to remind you of where you are lucky enough to be.