Brooklyn family.

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Point Lookout: Discover This Amazing 5-State View

Point Lookout: Discover This Amazing 5-State View

At Windham's 5-state lookout, you can see New York, Massachusetts, Connecticut, Vermont, and the White Mountains of New Hampshire all from one spot.

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We were intrigued when we passed the sign for Captain's Inn Point Lookout with the tagline, "Come for the view, stay for the company."

Captain's Inn Point Lookout

But the sign should actually say, "Come buy some food, then stay for the view." The viewing area is completely fenced off and heavily wooded, and if you aren't buying a meal, you aren't allowed to walk through the restaurant to see it. We thought about staying, but the dining room seemed a little too quiet and formal for our hyped-up children (though they do have a "kids corner" on their menu).

So, we made our way back to the car.

Captain's Inn Point Lookout

No biggie. Archer got right back into his foot-out-the-window Vacation Position, which is probably not legal.

Archer vacation postition

But we were only in the car for a few minutes, heading east on Route 23, before we got to a scenic overlook with an amazing view.

I tried to imagine dotted lined marking the borders between states, but all I could see was the breathtaking, limitless land before me. My photos don't begin to capture the beauty of the scene in real life.

No matter which way you lean politically, it's a magical view.

The hill is pretty steep but the railing makes this viewing area totally safe for a well-behaved 5-year-old. Ramona, our 2-year-old, tried to crawl under the rail a few times in hopes of picking some flowers. I grabbed her before she tumbled down the mountain.

Growing up in the Long Island suburbs and spending my summers upstate, I always wondered about the teenagers who live upstate full-time. I like to think that they're mostly like the kids pictured above, standing atop their cars, snapping photos of glorious views, and raising their arms to the sky, owning their mountains the way we owned our 7-Eleven parking lots, our diners, our goth coffee shops.

But then my teenage dreams were interrupted by Ramona shouting, "Archie, sit in my yap!" She has yet to master the "L" sound, but he knew what she meant.

We moved them back to their assigned seats and made our way to Cave Mountain, a place we've visited many times before, and enjoyed our milkshakes, burgers, and beers in a their casual dining room, which is always lively enough for our littles.

Hot Chicken Sandwiches & Cool Cocktails: Gracie's Luncheonette

Hot Chicken Sandwiches & Cool Cocktails: Gracie's Luncheonette

The Catskills Brunch of Your Dreams at Heather Ridge Farm

The Catskills Brunch of Your Dreams at Heather Ridge Farm