How to Plan a Ski Weekend in the Catskills
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Looking for the perfect winter getaway from New York City? The Catskill Mountains offer everything you need for a snowy weekend escape: ski slopes, charming towns, farm-fresh dining, and a cozy mountain hideaway to come back to at night.
I normally prefer to ski in higher altitude, dramatic landscapes, like in the Rockies. However the convenience and charm of East coast skiing can’t be denied. Keep an eye on the weather forecast to make sure you get fresh snow and you’ll be able to follow this itinerary for the perfect ski weekend in the Catskills.
Getting There (Friday)
If you are not within driving distance, then fly into Stewart International Airport (SWF), which is only about an hour and 15 minutes from the heart of the Catskills. This small airport offers a handful of flights daily that change seasonally. Luckily, they have had a direct route on Frontier and Allegiant from Fort Lauderdale.
However, be sure to account for any delays or cancellations. Our outbound flight ended up being canceled so we had to book a last minute flight into New York City and take a ride share to meet my brother who was living upstate.
Where to Stay
From SWF, it’s an easy drive to Pine Hill, a quiet mountain town that makes a great home base. We stayed at The Gateway at Pine Hill, a bed & breakfast with rustic charm and easy access to both Hunter Mountain and Belleayre.
Its cozy vibe and central location made it perfect for a ski-focused trip. If you visit during the fall or summer, they have great hiking trails on the mountain directly facing the bed and breakfast.
The breakfast is a fantastic and made to order. On the days we were there options included pancakes and breakfast burritos. The room layout was perfect for us, as we booked the connected family room, that allowed us to have privacy with two bedrooms but still be together.
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Saturday: Skiing Hunter Mountain & Snow Tubing Adventure
Morning: We kicked things off at Hunter Mountain, one of the most popular ski resorts in the Catskills. Hunter Mountain is part of the Epic Pass, so you can visit other resorts worldwide if you buy a multi-day or season pass. It’s about a 30-minute drive from Pine Hill, and it offers a great mix of trails for beginners and more advanced skiers.
Afternoon: After skiing, it was time for some laughs on the snow tubing hill — a fun way to switch things up after a day on skis. Hunter Mountain has great long tubing lanes that are fun for all ages.
Evening: For dinner, we splurged at Peekamoose Restaurant & Tap Room, one of the Catskills’ best farm-to-table restaurants. Think cozy cabin vibes, seasonal dishes, and cocktails perfect for warming up after a chilly day.
Sunday: Skiing Belleayre & Cozy Après Ski
Morning to Afternoon: Sunday was dedicated to Belleayre Mountain, just minutes from Pine Hill. This resort is a local favorite, known for its family-friendly atmosphere and long runs through the trees. We wanted to ski two different mountains just to experience both options. The video below breaks down the quick pros and cons of each.
Après Ski: Back at the Gateway at Pine Hill, we treated ourselves to their hot chocolate happy hour — exactly what you need after a day on the slopes. They also have an extensive collection of Amaro you can taste, which was a very interesting experience since I was not that familiar with the liquor.
Evening: After returning our rental gear, we headed to Tito Banditos, a laid-back spot serving Mexican comfort food that hit the spot. We have a lot of great Mexican food where we are from, South Florida, and I have to say Tito Banditos is the absolute best we’ve had, especially out of state. The owner takes a lot of care to honor Mexican recipes and add modern flair with local ingredients.
Extra Stops & Day Trips in the Catskills
If you have more time in the region, the Catskills are full of hidden gems worth exploring:
- Two Stones Farm & Creamery (open afternoons) – A small farm offering locally made cheeses and fresh cream.
- Roxbury Mountain Maple & Tree Juice Maple Syrup – Classic Catskills maple farms where you can taste and buy small-batch syrup.
- Cody’s Sugar Shack – Another local spot for maple syrup lovers.
- Woodstock – The legendary town filled with quirky shops, art galleries, and a free-spirited vibe.
- Franklin D. Roosevelt Historic Home – History buffs will love visiting Hyde Park, the home of the 32nd U.S. president.
- Bear Mountain Ice Rink – Outdoor skating surrounded by snowy scenery.
- Snowshoeing at Minnewaska State Park – Take a lesson and explore the beautiful winter trails.
- Adirondack Pub & Brewery Ice Bar – A seasonal pop-up bar carved entirely from ice, serving craft beers and cocktails.
- Harney & Sons Tea (in Millerton) – Visit their flagship shop for premium teas and cozy tastings.
- Walkway Over the Hudson – At over 1 mile long, this pedestrian bridge offers sweeping views of the Hudson River Valley.
- Vanderbuilt Mansion Historic Site– Guided tours of a guided age mansion, surrounded by a large park with views over the Hudson River.
We had most of Monday before our evening flight to explore, so we chose to visit Woodstock and the Franklin D. Roosevelt Historic Home. The Main Street of Woodstock had lots of cute little shops, from handmade candles, to curated vintage. The Franklin D. Roosevelt Historic Home offered an extensive museum collection, access to the library and gardens.
We took in the views at the Vanderbilt Mansion before our flight, since the grounds remain open even after the mansion visiting hours. We’d love to come back by another time to visit the mansion interior.
Final Thoughts
Whether you’re carving down Hunter Mountain, sipping hot chocolate by the fire, or sampling maple syrup at a local farm, the Catskills deliver the perfect balance of adventure and cozy mountain charm. With its proximity to New York City and plenty of ski resorts, it’s an easy weekend getaway that feels like a true winter retreat.
For a ski vacation out west, check out my comparison of the Sheraton and Doubletree in Park City. If you have lots of credit card points and are looking for ski-in/ ski-out stays, see my roundup of the best luxury hotel options on points across the country. To stretch those points even further, here’s a list of the best affordable ski resorts on points.
