Field Trip: Oyster Bay, Long Island

On occasion, I’ll publish a day trip idea, and I am counting on readers to send suggestions. This one goes out to my Aunt Joan, who knows the mean streets of OB a lot better than I do.

The hamlet of Oyster Bay, Long Island

By train: 1:15 from Penn to Oyster Bay, but you have to change at Jamaica so they can hitch up the mules.
By car: It’s only 38 miles, but it’s the LIE, so count on 1.5 hours on NON peak times

This is my hometown (well, I am from an even smaller town two miles north) so I never thought of it as a vacation destination till I learned my Tribeca neighbors had a summer home there. So I tried to look at it with fresh eyes, and sure enough, it totally qualifies as a field trip. It’s a beach town — on a bay off Long Island Sound — and much about it is centered around the water. The parks are grassy, beachy and uncrowded. The train stop is right at the beach.

There are some businesses in town that have been there since I was a kid but there are newcomers too that add to the experience.


  • I would make my first stop Southdown Coffee for whatever caffeine drink does it for you plus a scone (they also have small sandwiches). There’s also Taby’s, for a classic Greek diner that can handle breakfast, lunch or dinner.
  • My afternoon stop would be the Oyster Bay Brewery, for the obvious reasons.
  • And if you clean up good, 2 Spring and Wild Honey are both reliable.
  • But the can’t-miss is Bonanza Stand, which was in fact founded in that very shack by my grandmother’s classmate. (My mother went to high school with the son, I went to high school with the grandson, you get the idea.) My order is a dog with kraut and mustard and a lemon ice, which was all they served when I was a kid. (Joan would get a dog with kraut and mustard, hold the dog.) But now there’s all sorts of fries, chicken tenders and every flavor of ice.

My cousin and I make it a point once a month to get to Oyster Bay Foot Relax Spa, where a 30-minute foot massage is $25. Call to check. 516-802-3377

It’s residents only parking at Teddy Roosevelt Memorial Park, but you can park in the giant free lot at the train station on the other side of the tracks and walk the two minutes in. There are changing rooms, bathrooms, playgrounds, tennis courts, etc etc. Take your beach chair and set up for the day. This is the bay off the sound, so no waves but good breezes. We taught our kids to ride bikes there, since you are allowed to ride on the lawns.

Oyster Bay Cove was the summer home of Teddy Roosevelt and his home at Sagamore Hill is a great visit. You’ll need a car or a taxi — it’s about three minutes out of town. The house tour is amazing — the place is filled with elephant tusks and all sorts of contraband — but the grounds and the walk to the beach are also worthwhile.

The Raynam Hall Museum is based in the home of Robert Townsend, one of Washington’s chief spies during the American Revolution.

If you have wheels, there are tons of other nature options: Shu Swamp is a small loop through a very pretty wetland; Planting Fields Arboretum is a former estate with beautiful gardens and walking paths.



  1. Great overview of OB! Wild Honey is great – their Mussels are to die for!

  2. Looks so pretty.. thanks for the trip idea!

  3. So sweet and beautiful.

  4. TR house is a gem. Has a Latin quote at entrance. His Nobel Peace Prize is displayed (Russian Japan war). The grounds are terrific views, reminded me a bit of the other Roosevelts upstate Hyde Park off Hudson. Don’t rem the town too much. Rocky Point out past SUNY is kinda of a find too. Small but rocky terrain.

  5. I have lived in small-town-USA Oyster Bay for 50 years. My children loved growing up here, and I stayed after they flew the nest. It is a place where natural beauty and history converge and where oysters abound! The presence of TR is palpable!!