Who’s the Boss in Westchester?

New Yorkers love to escape the hustle and bustle of the city for one of the tri-state area’s many amazing suburban communities. And one favorite is Westchester County, NY.

I absolutely love Rye, NY and the surrounding Westchester area. There’s plenty to see and do and you can spend an entire afternoon just drooling over the gorgeous homes in this posh community.  A quick drive from New York City, New Jersey or Connecticut makes this area a perfect day trip for locals, but there’s enough to do to make it a weekend trip for out-of-towners too.

Here are some of my picks for fun spots in the Rye, NY area.

The Who’s The Boss House:


Sitcom lovers of the 80’s and 90’s cannot forget that classic opening scene when Tony Micelli drives his beat-up van down the quaint Connecticut street speckled with colorful Autumn leaves. Who’s The Boss was such a favorite show of my childhood, and I remember every little thing about the picket fence-lined Connecticut house where the Micelli/Bower crew lived. But guess what?! The house is NOT in Fairfield, Connecticut where the show was set! It’s in a lovely neighborhood in Rye, NY. We checked it out in person and it is beautiful! And I could not resist dressing my mini Micelli for the role 😉




Rye Business District:

Right down the street from the iconic TV house, the business district in Rye is filled with adorable shops, bakeries, restaurants, and cafes. If you’re looking for old-fashioned charm, then head to Purchase Street. Take a peek in Arcade Booksellers with its wall-to-wall, floor-to-ceiling books.


Then when you’re hungry, be sure to check out the trendy vegetarian cafe Rosemary & Vine. It has lots of vegetarian and vegan options made from scratch in a yummy Mediterranean style. It’s quaint but still kid-friendly. I really enjoyed my quinoa black bean burger (ask for tzatziki on the side — trust me!) and my son’s flatbread pizza and freshly cut whole apples and oranges were a healthy win.




Beaches and Parks:

Westchester has great beaches and waterfront parks to visit in the nice weather with beautiful views of the Long Island Sound. Check out the Rye Town Park and Beach or Harbor Island Park with its playground and marina.

Rye Playland:

This iconic amusement park has been a favorite family attraction of Westchester since 1927. Sitting on the shores of the Long Island Sound, this spot boasts not only amusement rides and games, but also a boardwalk, pool, beach, and mini golf course. Open from mid-May to mid-September, Playland is full of old-world festival fun and a perfectly playful spot tucked away in this upscale community.


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