Plan-it Poole: Travel Hacks, Inspiration & Itineraries

Catskills Forever

There's a spot in upstate New York that can still capture my heart...

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Amie O'Connor Poole
Jul 29, 2025
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OUR LAKE HOUSE AIRBNB IN THE CATSKILLS

Places change, politics shift and as long-standing fans of the great American road trip we’d started to wonder if we’d ever embark on one again.

Fortunately, the natural beauty and retro charms of the Catskills can make you feel like you’ve hired a time machine (rather than a cheap rental car).

Meet the Catskills

KAATERSKILL FALLS

Part of New York State, just two hours drive north along the Hudson Valley from Manhattan, the biggest draw of the Catskills is its natural beauty. The area’s name comes from the Catskill Mountains, that loom ever present and both the Mohonk Preserve and Minnewaska State Park offers stunning scenic trails. Giant Ledge boasts incredible views over the whole area and Kaaterskill Falls, a two-tiered natural waterfall, is thankfully easy to access without a lengthy trail from the car park.

But as charming as the area’s peaks and lakes are, for me, it’s the small towns, roadside diners and random attractions are what makes the Catskills so undeniably adorable.

WOODSTOCK MUSEUM AT BETHEL WOODS

We’d heard about the area’s best-known ticketed attraction, the Bethel Woods Center for the Arts (home to the Woodstock festival), but our favourite discoveries came from just driving around and exploring, pulling over to see the World’s Biggest Kaleidoscope at Emerson, climbing giant fire towers for the views and playing pooh sticks on historic covered bridges.

COVERED BRIDGES, (THEY ARE FASCINATING, HONEST)

Much of Apple TV’s Severance was shot in the Catskills which for us created extra geeky points.

The Towns

The Catskills’ roads create a kind of loop around the mountains and parks meaning it’s easy to tour the main towns in a circular route.

THE PHOENICIA DINER

We loved Phoenicia for its diner (one for the Severance fans), Woodstock for its colourful indie shops, Liberty for its small town architecture and Callicoon for its local brewery and amazing art deco cinema, which is an incredible space (even if you find yourself watching the Minecraft movie).

SHOP IN LIBERTY

It’s a pretty spread out and at times remote area, where a car is essential, so it’s important to choose where you stay wisely.

THE CALLICOON THEATRE

Where to Stay and Eat in the Catskills

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