Rye Playland (in Rye, NY) is a triple bonus!
Not only does Rye have a boardwalk, a beach and a dog-friendly restaurant, you can also see the gorgeous Art Deco Buildings and the Zoltar, the original fortune telling machine from Big, which was filmed at Rye Playland.)
You can walk the boardwalk where they serve fresh coconut and mango drinks made on the spot, there is a dog-friendly park, and you can have a cocktail and lunch or dinner at the Tiki Bar.
This is not a gourmet restaurant, but the fries were great, the service very nice and the view unbeatable.
Dogs can run free on the beach at Rye Playland after Labor Day, although Bosqui is too small to run free with other dogs. From bringfido.com—Playland Beach is located on the grounds of Playland Park Amusement Park. Dogs are welcome to join their owners on the beach from October 1st until April 28th. There is a limit of 3 dogs for each owner and dog walking services are prohibited all year round. Make sure you keep Fido on a leash under six feet.