The Catskills are made for the kind of weekend where you leave the city behind, buy a sweatshirt you probably didn’t need (I brought one home from Camp Catskill in Tannersville), and spend a few days bouncing between tiny towns, mountain views, waterfall hikes, coffee shops, and really great meals. That’s exactly the kind of trip my wife and I wanted to celebrate our third wedding anniversary.
We stayed at Camptown in Leeds, New York, and it ended up being the perfect home base for a long weekend exploring the Catskills and Hudson Valley. The hotel has this fun, slightly kitschy, retro-camp energy that makes you feel like you’ve escaped real life for a few days. It’s stylish without taking itself too seriously, which is exactly the sweet spot for a Catskills getaway.
Over the course of the trip, we explored Cold Spring, Storm King Art Center, Kaaterskill Falls, Hudson, Catskill, Tannersville, New Paltz, Kingston, Saugerties, Woodstock, and Beacon. It sounds like a lot, and it was, but in the best way. This was a trip built around scenic drives, good food, cute shops, waterfall mist, pool drinks, and the deep satisfaction of doing just enough before retreating back to the hotel for sauna time.
Day 1: Cold Spring, Storm King, and Camptown
We woke up early so we could get on the road from Baltimore and make the most of the day.
Our first real stop was Cold Spring, a charming town right along the Hudson River. It’s a perfect road trip break: cute shops, river views, and plenty of places to wander before getting back in the car.
For brunch, we stopped at The Foundry Rose, and the standout was absolutely the lemon blueberry pancakes. They were bright, sweet, and exactly the kind of breakfast that makes waking up early feel worth it.
From there, we headed to Storm King Art Center, an outdoor large-format art museum and sculpture garden. Once we arrived, we rented bikes on-site and rode a four-mile loop through the grounds to see the art. Storm King is massive, so biking made it easier to see more without feeling rushed.
Where We Stayed: Camptown
We absolutely loved Camptown. The whole property feels like a modern summer camp for adults — pool, pool bar, fire pits, sauna, and enough vintage-inspired details to make the whole stay feel playful and relaxed.
After our first day on the road, we checked in and immediately headed for the pool with drinks in hand. After a quick swim, we warmed up by the fire pit, which felt like the exact right way to start a Catskills weekend.
The hotel also has an on-site restaurant, Casa Susanna, which made the stay feel even more complete. I love when a hotel restaurant is actually worth staying on property for, and Casa Susanna absolutely was. The menu leans modern Mexican (no chips and salsa on this menu), and the best bite of our dinner was the asparagus — one of those deceptively simple dishes that ends up being the thing you keep talking about later.
Camptown worked perfectly as a home base because it gave us easy access to Hudson, Catskill, Tannersville, Woodstock, Kaaterskill Falls, and a handful of other towns without constantly packing and unpacking. If your ideal Catskills trip includes hiking in the morning, wandering small towns in the afternoon, and returning to a pool, sauna, or fire pit by evening, this is exactly the vibe.
Day 2: Kaaterskill Falls, Donuts, Hudson, and Dinner in Town
The next morning, we woke up early again to beat the rain in the forecast for most of the weekend and get a hike in before the weather turned.
We headed to Kaaterskill Falls, one of the most famous waterfalls in New York. It’s a two-stage waterfall with a total drop of 260 feet, making it one of the highest waterfalls in the state. It’s also one of America’s oldest tourist attractions, which made the whole experience feel even cooler.
We started at the top and worked our way down. The trail was pretty steep in parts, but the views were absolutely worth it. We stopped at the midpoint between both drops, which gave us a beautiful view of the falls and a much-needed breather. Wear good shoes and be prepared for some incline.
After the hike, we stopped at Fred’s Coffee and Donuts. The donuts are glazed to order, which means they come out warm and fresh, aka exactly what you want after a hike. Then we went back to Camptown for sauna time, which was the perfect rainy-day reset.
Refreshed and in the mood for lunch, we drove across the river to Hudson, which quickly became one of my favorite towns of the trip. It has a great mix of shops, restaurants, coffee, design stores, and that very specific Hudson Valley energy that makes you want to wander slowly. We had lunch at Le Perche, stopped at Return Brewing, walked along main street, explored Catskill for a bit, and ended the night with dinner at Feast & Floret in Hudson. The service was amazing and the chicken milanese was outstanding. Thin and crispy, just as it should be.
If you like scenic hiking trips, you might also enjoy my Shenandoah National Park guide.
Day 3: Gracie’s, Tannersville, Kingston, Saugerties, and Woodstock
The next morning started with breakfast at Gracie’s Luncheonette, which also gave nostalgic upstate NY vibes. The waffles and donut were both outstanding, and it had that classic luncheonette feel with food that still felt thoughtful and craveable.
After breakfast, we grabbed coffee at Hartland in Leeds, then drove past the nearby ski mountains, including Hunter and Windham. Even outside of ski season, the drive through the area is beautiful.
We stopped in Tannersville, where I bought a sweatshirt, because apparently that’s who I become in mountain towns. Then we spent the afternoon exploring New Paltz and Kingston, which are both great for walking around, shopping, and building a loose afternoon itinerary.
For lunch, we stopped at Tortilla Taco Bar in Kingston, then made our way to Alleyway Ice Cream in Saugerties for an afternoon treat. If you also love building trips around sweets and scoop shops, I have a full guide to the best ice cream in Baltimore.
For dinner, we drove into Woodstock to eat at Big Night, a Southeast Asian restaurant. The dumplings were amazing and easily one of the standout bites of the trip. Woodstock is definitely worth visiting while you’re in the Catskills, even if you only go for dinner and a short walk around town.
Day 4: Hudson, Beacon, and the Drive Home
On our final morning, we checked out of Camptown and headed back across the river to Hudson for coffee at Hudson Roastery. From there, we drove about an hour south toward Beacon, with a quick stop at a Taste NY rest stop to browse local snacks and products.
Beacon made for a perfect final stop before the longer drive back to Baltimore. We popped into a cute glass studio, wandered through a few shops, and grabbed lunch at The Beacon Daily. The sandwich was epic — exactly the kind of travel-day lunch I want before a long drive. Before getting back on the road, we also grabbed coffee at Big Mouth Roasters.
If you like trips built around small towns, scenic drives, and food stops, this Catskills itinerary pairs really well with my I-83 road trip from Baltimore to Harrisburg. And my Virginia I-81 road trip guide.
More Travel Guides You’ll Love
If you’re looking for more weekend trip ideas, you might also enjoy:
- The Perfect Long Weekend in Canandaigua, NY
- Long Beach Island, New Jersey Travel Guide
- 3 Days on Tilghman Island, Maryland
- Getaway House Asheboro, North Carolina
- A Weekend in Floyd, Virginia
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