How to Have a Perfect Weekend in the Catskills

Last Updated on April 13, 2024 by Adam Watts

A Weekend in the Catskills – FRIDAY

Want a break from city life? Whether you’re coming from the west coast or New York City or somewhere in between, there’s plenty to do in a weekend in the Catskills.

Curiously named – meaning “Cat Creek” in Dutch, named by early Dutch explorers – the Catskills are a small part of the wider Appalachian Mountains and are in southeastern New York State. For context, because most people associate New York State only with New York City, the Catskills are a two-hour drive northwest of the Big Apple. (And to scare people that are from small countries, you can start in the southeast part of New York, drive two hours north west, and still be in the southeast corner of the state. I’m from the UK, and if you drive two hours north west from where I grew up, I’d end up among people who speak a freakish form of English I’d need a translator for.)

Anyway, all that introduction is making me hungry. So let’s rent our car and head north up the Taconic State Parkway, driving extremely carefully because the police here are apparently infamous for pulling people over. Stop at PAKT for some brunch options more creative than the usual French toast or breakfast burrito (how about a blueberry chipotle pulled pork sandwich? Or a buttermilk biscuit with sausage, scrambled egg and gravy?).

If you gorge too hard on too many of those buttermilk biscuits, I’d recommend checking into your Airbnb then finding somewhere to lie down in some grass and watch the clouds drift overhead. We had access to a creek near our cabin in the woods so we sat by that and listened to the soft tinkling of lazy water. Only three hours ago we had been stuck in idling traffic trying to escape the city, yet it already felt a lifetime ago.

In the late afternoon, hop back in the car and drive around looking for short hiking trails. We found a quiet one, hiked maybe half a mile, then realized that we’re city folk and what if there are bears here? What if those bears are hungry?? What if a bear cub comes tottering over to us and his mommy comes looking for him and sees us near him and starts running towards us???

We promptly returned to the safety of our car, but then decided that logic was on our side. There can’t be that many bears around, especially not close to hiking trails that show up on the first page of google results and therefore must be popular, so it would be incredibly unlikely we’d even see one.

But we passed an isolated house and there one was! A black bear, casually sniffing around the back of the house, and then climbing up into a nearby tree.

For dinner, check out Peekamoose Restaurant for culinary excellence. The menu rotates but I can confirm our meal was fantastic and everyone else’s looked fantastic. They have a formal dining area, a dingy tavern-like bar, and an outdoor patio with a fire pit, so sit wherever takes your fancy.

A Weekend in the Catskills – SATURDAY

No matter whether you want just a cup of coffee or a breakfast feast, head to Phoenicia Diner for the quintessential “life in the country” diner experience. Big windows line one wall and inside is packed with red-cushioned booths and a row of silent, heavy-set men sit on stools against the front counter, shoveling pancakes and omelettes into their mouths. It very much has a “heart of the community” feel to it, with ads for local services and a “take a book, leave a book” shelf by the front door.

Our main activity for the day was a hike to Kaaterskill Falls. We parked at a gravel lot along a road, then walked ten minutes back along the road to the trailhead. Then it was a few miles up and down and around a wooded trail to the double-level waterfall, where we dipped our feet and people-watched for a long time. Unlike the previous day where we’d hiked a short way alone, this was extremely busy, and we’d have to stop and let people pass us along a narrow stretch. The route is suitable for kids, pets, pretty much anyone and everyone.

In the afternoon, drawn by the title of “world’s largest”, we stopped by Emerson Resort & Spa to check out its kaleidoscope. I’m a sucker, I’d want to see the world’s largest anything. World’s largest ice cream scoop? Sure. World’s largest rubber duck? Hell yeah. World’s largest “world’s largest” sign? Just try and stop me.

So when we passed a sign for the world’s largest kaleidoscope in the morning, I knew we’d have to come back to see it. And see it we did. We paid our $5 apiece and, as I cast a sideways glance at the pair of rambunctious kids and their encouraging parents, the woman offered us a private viewing if we were prepared to wait until the kids were done.

Prepared to wait we were. And I’m glad we did. The kaleidoscope is inside a former grain silo and we had it to ourselves. We lay down on the floor and stared up at the ceiling 56 feet above us and a narrator soothingly talked to us about something or other; it was difficult to focus on the sound when the lights and shapes way above us were so pretty. The kaleidoscope’s main presentations utilize video playing off a three-dimensional three-mirror system that creates “a precise pyramid tapering from 15 feet at the bottom to five feet at the top, which reflect a constantly evolving virtual sphere with a 50-foot radius” (from their website).

Grab dinner in Phoenicia or any other nearby town, then treat yourself to a bottle of wine and have a cosy evening back at your cabin.

A Weekend in the Catskills – SUNDAY

On your final day, after checking out of your Airbnb, head east to Woodstock to check out its flea market, absorb a little peace and love, and also absorb some pastries and juice from the Bread Alone Bakery.

To break up the drive back to New York City, stop at Innisfree Gardens ($10 apiece) to end your weekend in the Catskills. Spend a few hours enjoying the final peace and quiet before hitting the city. Innisfree is based on Chinese & Japanese design principles, and features paths, waterfalls, and a large lake. It’s beautiful and well worth taking your time over. Explore every nook and cranny of the gardens, but also make time to sit on some grass by the lake and close your eyes for a while.

The last stop on your weekend tour, if you’re based in New York City, should be to make the most of your rental car by visiting a Walmart and stuffing it to capacity with boxes of pasta, cans of vegetables and soup, 18-packs of beer, a houseplant or two, a new laundry hamper, and maybe a new TV if self-control is an issue for you. When are you likely to be able to do this again? Tomorrow you’ll be back to buying one bag of groceries at most and struggling home with it.

And that’s it. That’s how you have a perfect weekend in the Catskills. If you take any or all of this advice, or you spend a weekend in the Catskills doing totally different things, let me know in the comments below! For a day trip recommendation from New York City, check out Storm King Art Center. Read it all about it here.