Day Trip: Shelter Island

I have a confession to make. Before I met my husband, I thought Long Island was a small blip off Manhattan where a small grouping of people said things like “Tawmmy wawnts a hawt dog” and Ray Romano constantly evaded his mother.

My deepest apologies. I now know better. (Although I still can’t watch Everybody Loves Raymond without cringing.)

Case in point? Today’s featured day trip to Shelter Island.

Shelter Island is an 8000 acre island that is located in between the two forks of Long Island’s east end. About one-third of the island is protected and will be kept in a forever-wild state. The island is accessible by ferry.

While we saw many people at the beaches, we opted to spend most of the day biking taking in the scenic views. I was in for a rude awakening – after the nice, flat roads of Cape Cod, I definitely got my workout biking up some of these hills!

Bike Rentals are available in town at Piccozzi’s Garage Bike Shop. I would say that’s an unbiased recommendation, but it’s not. Not only are they related to Moose, but I am pretty sure they are the only bike shop on the island too.

We also stopped by Reddings Market for lunch.

I highly recommend the sweet potato waffle fries! And the caprese panini. YUM. We ate outside on weathered cafe tables and enjoyed people watching, cool car sitings and petted the many cute leashed dogs that passed by our table.

The market was filled to the brim with snacks, sodas and other artisinal food pantry items.

I had massive chalkboard envy at Reddings! Look at that huge chalkboard wall covered with colorful and delicious menu options.

There were beautiful scenes at every turn. If you’re looking for a lazy (and aerobic – the biking, remember?) day, Shelter Island is a great place to visit.

Also, barnwood is my new favorite thing. Anybody have an old barn they are knocking down? I wouldn’t mind trashpickin’ at your place.

Shelter Island is home to many other sites:

Like the Pridwin Hotel, if you’re looking to live out your “Nobody puts Baby in a corner” fantasy. (My sister-in-law and I both decided this family summer camp is just like the one in Dirty Dancing.)

Also, the Perlman Music School, Itzhak Perlman’s school, which holds many free concerts in the summer.

We ended the day with dinner at Fresh the restaurant at Shelter Island Country Club. The restaurant is located on the highest point on Shelter Island accessible to public, so the views down the fairway are lovely.

How do you feel about Long Island? Biking up hills? Putting Baby in a corner?

5 thoughts on “Day Trip: Shelter Island

  1. Oh my gosh! I LOVE Shelter Island. I spent a summer as a camp counselor working at Camp Quinipet and Retreat Center–right down the street from the Pridwin and the music camp. It did get a little claustrophobic living on the island for about 6 weeks (but I didn’t have my own car!) but it is such a beautiful place most people have never heard about (Martha’s Vineyard and Cape Cod get more press). It’s my parents’ dream to own a summer house there!

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