You’re driving up the NY-87, the Thruway. The concrete starts to give way to those rolling, hazy blue peaks that inspired an entire school of landscape painting, and suddenly you realize you have no idea where you’re actually going. It happens to everyone. People treat the Catskill Mountains like a single neighborhood. In reality, this region covers over 6,000 square miles across four counties. If you’re looking for what to do Catskills style, you have to stop thinking about it as one "place" and start looking at it as a collection of wildly different vibes. You’ve got the high-end, $800-a-night "Brooklyn North" scene in Livingston Manor, and then you’ve got the rugged, "I might actually see a bear" wilderness in the Slide Mountain Wilderness.
Honestly, the biggest mistake people make is trying to do too much. They want the cideries, the 3,500-foot peaks, and the antique shops all in one Saturday. You’ll spend four hours in your car just trying to cross the Pepacton Reservoir. Don't do that.
The Geography of Your Weekend
The Catskills are split into roughly three zones. The Eastern Catskills—think Hunter and Tannersville—are high-peaks territory. This is where you go if you want vertical gain. It’s rocky. It’s steep. It’s where Kaaterskill Falls is located, which is arguably the most famous waterfall in the state.
Then you have the Western Catskills. Places like Delhi and Bovina. This is farmland. It’s rolling hills, cows, and the kind of quiet that actually makes your ears ring if you’re used to the city. It’s slower.
Finally, you’ve got the Sullivan Catskills to the south. This is the "Borscht Belt" heartland. It’s where Bethel Woods (the site of the 1969 Woodstock festival) is. This area has seen a massive resurgence lately with boutique hotels popping up in old motels.
The Kaaterskill Trap
If you Google what to do Catskills, Kaaterskill Falls is the first thing that pops up. It’s stunning. Two tiers, 260 feet of falling water. But here is the reality: on a Saturday in July, it looks like a subway platform. You will be fighting for a parking spot.
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If you want the view without the crowd? Try the Escarpment Trail. Specifically, head to Inspiration Point. You get the same dramatic drop-offs and Hudson Valley views, but you won't be shoulder-to-shoulder with people in flip-flops who didn't realize they were going on a hike.
High Peaks and Hard Lessons
Let's talk about the 35ers. These are the 35 peaks in the Catskills over 3,500 feet. Slide Mountain is the highest at 4,180 feet. It’s a great hike, relatively gradual compared to some of the others.
But if you want a challenge, Peekamoose and Table mountains are where it's at. The Blue Hole is nearby—a famous swimming hole with crystal clear, freezing water. Note: you now need a permit from the DEC (Department of Environmental Conservation) to visit the Blue Hole on weekends between May and September. Don’t just show up. A forest ranger will be there, and they will turn you around.
Hunter Mountain is more than skiing
In the winter, yeah, it's a zoo. But in the summer, the SkyRide takes you to the summit without the sweat. There is also the Zipline Canopy Tour. It’s one of the highest and longest in North America. It’s terrifying. It’s also expensive, so budget about $150 per person if you’re going for the big tour.
Where to Actually Eat
Food in the Catskills has changed. It used to be diners and dusty pizza joints. Now? It’s world-class.
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- Phoenicia Diner: You’ve seen it on Instagram. It’s iconic for a reason. The trout skillet is legit. Expect a two-hour wait on Sundays.
- The Wayside Cider Taproom: Located in Andes. They use wild and abandoned orchard apples. It’s basically a community living room with great booze.
- Brushland Eating House: In Bovina. It’s tiny. It’s sophisticated but doesn't feel snobby. They do a communal-style dinner that feels like a wedding in the best way possible.
Be warned: many places in the Catskills are closed on Tuesdays and Wednesdays. This catches people off guard constantly. You’ll be starving in a small town at 7:00 PM on a Tuesday, and your only option might be a gas station sandwich. Plan accordingly.
The "Secret" Spots No One Mentions
Everyone goes to Woodstock (the town). It’s cute, but it’s touristy. If you want a more authentic feel, head to Sharon Springs or Hobart. Hobart is a "Book Village." There are literally more bookstores than regular shops. It’s quiet and strange and wonderful.
The Ashokan Reservoir is another one. Most people just drive past it. There is a paved path that runs along the water with incredible views of the high peaks. It’s flat. You can bike it. It’s perfect for when your legs are shot from hiking the day before.
Fly Fishing is a Big Deal
The Catskills are the birthplace of American dry-fly fishing. The Beaverkill and the Willowemoc are legendary. Even if you don't fish, visiting the Catskill Fly Fishing Center and Museum in Livingston Manor is worth an hour. It’s niche, sure, but the history of how this sport shaped the local environment is actually pretty fascinating.
Getting Around
You need a car. Period.
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There is a bus—the Trailways—that goes from Port Authority to towns like Kingston, Phoenicia, and Hunter. It’s reliable. But once you get off that bus, you are stranded. Uber and Lyft basically don't exist here. Even if the app shows a car, it’s probably twenty miles away.
Cell service is also a nightmare. Download your Google Maps for offline use before you leave Kingston. Once you hit the notch on Route 28, your GPS will likely spin into oblivion.
What Most People Get Wrong About "Woodstock"
Common misconception: The Woodstock festival happened in Woodstock.
It didn't.
It happened in Bethel, about 60 miles away. If you go to the town of Woodstock looking for the hallowed ground where Jimi Hendrix played, you’ll find a lot of tie-dye shops but no festival site. For that, you need to go to the Bethel Woods Center for the Arts. They have a fantastic museum there, and the concert venue is world-class.
Seasonal Reality Check
Spring (Mud Season): It sucks. From late March through May, the trails are a slurry of grey mud. The black flies come out in late May. They bite. Hard.
Summer: Perfect weather, but the weekends are packed. Go mid-week if you can.
Fall: Peak foliage is usually the second week of October. It’s breathtaking. It’s also when traffic on Route 28 rivals the Long Island Expressway.
Winter: Great for skiing, but many smaller shops and seasonal restaurants shut down completely.
Actionable Steps for Your Trip
- Download the Avenza Maps app. It uses your phone's GPS (which works without cell signal) to show exactly where you are on DEC trail maps. It's a lifesaver.
- Book your dinner reservations two weeks out. If you want to eat at places like Stissing House or Peekamoose Restaurant, don't wing it.
- Check the DEC "Hike Smart" webpage. They post weekly updates on trail conditions. If there was a big storm on Tuesday, the trails will be washed out on Saturday.
- Buy a New York State Empire Pass if you plan on visiting multiple state parks (like Minnewaska or North-South Lake). It saves you a ton in parking fees.
- Support the locals. Buy your groceries at the farm stands. The Catskills' economy is fragile and relies heavily on seasonal tourism.
The mountains aren't going anywhere, but the quiet spots are getting harder to find. Respect the "Leave No Trace" principles. Pack out your trash. Don't blast music on the trails. Keep the Catskills wild so they’re still worth visiting ten years from now. Get off the main drags, take a random turn onto a county road, and see what you find. That's usually where the real magic happens anyway.