The Skiing Issue

Here's where to ski in the tri-state area, where to stay, what to pack and our favorite gear...

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Let’s be clear: I don’t ski or participate in winter sports (which feels very on-brand for someone from Hawaii). That said, my husband is passionate about skiing, my kids are avid skiers, and I’ve proudly stepped into my role as a ski mom. The learning curve was steep (pun intended), and I’m happy to share what I’ve learned so far about skiing in the tri-state area. I imagine much of what follows applies to snowboarders too—I just haven’t had to cross that bridge (yet).

• Mohawk: We’re here weekly from January through March, so this is the mountain I know best. Their ski program operates on a lottery system, with fall sign-ups for children ages five and up. You can also book one-off lessons, but they must be reserved two weeks in advance—and you need to be on top of it, as spots sell out quickly. This mountain works well for our family: the skiing is good enough, we’ve been happy with the instruction, the location is great (I’ve loved exploring Litchfield County), and it’s closer than many other options, making weekend trips manageable. It’s an easy mountain to learn on, yet older kids in the ski racing program still enjoy it and haven’t outgrown it. There’s one simple lodge and it’s nothing fancy.

  • About a 2-hour drive from NYC.

  • Where to stay: Litchfield County has some great Airbnb options. I love the town of Litchfield, Washington, New Preston, but my favorite is Kent—all within a manageable drive to Mohawk.

  • Pro tip: If you can sneak away or are craving a more luxurious stay, head to The Mayflower—its spa is one of my favorites.

• Catamount: This is the next step up from Mohawk. It’s a larger mountain with more of the amenities you’d expect from a Western-style ski resort—multiple large lodges, better food options, and live music on weekends. Catamount offers more flexible ski school options, including one-day drop-in programs. While lessons still book up quickly, it’s generally easier to secure a spot than at Mohawk. Like Mohawk, Catamount has an excellent ski program for children ages five and up, run on a lottery system released in the spring for the following winter season.

  • About a 2.5-hour drive from NYC.

  • Where to stay: Little Cat Lodge is at the mountain, so you couldn’t be closer and recently renovated. The Berkshires have a myriad of options for accommodations. Prospect Berkshires is a great option right near the mountain.

• Windham Mountain: This is the nicest of them all if you’re looking for an Aspen-like vibe. The mountain and resort recently received a major capital investment from the team behind Blackberry Farms, resulting in upgraded trails, infrastructure, restaurants, and lodging. While it operates as a private mountain and membership club (with certain lodges, bars, and accommodations reserved for members) the general public can still purchase lift tickets and book lessons on designated areas of the mountain. Like the others, it offers seasonal programs for children ages five and up, sign-ups open in March, and open to the public. For daily drop-in lessons, be sure to book early, as they fill up quickly—especially on holiday weekends.

  • About a 2.5-2.75-hour drive from NYC.

  • Where to stay: Wylder Windham is a fantastic hotel and an ideal place for families. There’s always something going on—from a basement packed with kids’ games and activities to multiple bars and restaurants—making it a truly great family-friendly hotel. Hotel Vienna is a nice back-up option.

• Hunter Mountain: Located in the Catskills, this mountain offers a bit of everything. It’s larger than many others in the region and has the most to do. While its distance makes it less convenient for a quick weekend trip, it boasts greater terrain variety and more challenging runs that appeal to experienced skiers. Similar to Windham Mountain, it has a livelier lodge atmosphere, with multiple dining options, après-ski activities, and events. Ski programs start in mid-December for children ages five and up—earlier than the other mountains that start in January.

  • About a 2.5-2.75-hour drive from NYC.

  • Where to stay: There are hotels and lodging on the mountain, but I’d still highly recommend Wylder Windham (see above).

• Butternut: This mountain is a great all-around option. It’s farther from the city, but that also means fewer crowds and more affordable pricing. It’s similar in scale to Catamount, though many find the terrain more enjoyable. It offers a good mix of beginner, intermediate, and some advanced runs. There is a multi-week program for ages six and up (older than the others). The vibe is laid-back and retro New England rather than polished like Windham or Hunter, but it’s well run and charming.

  • About a 2.75-hour drive from NYC.

  • Where to stay: You’re right in the heart of the Berkshires, so there are plenty of great Airbnb options. For hotels, Prospect Berkshires is an excellent choice, or if you’re traveling with kids and want something simple The Red Lion Inn is very old-fashioned but gets the job done.

• Mount Peter: We tried this mountain for the first time when my son was just learning to ski. It’s an entry-level mountain with just the bare essentials at the base, but its proximity to the city makes it perfect for a day trip. There are ski lessons and a smaller weekly program for kids ages six and up. On your way home, consider stopping in Tuxedo Park for lunch, where you’ll find plenty of dining options.

  • About a 1.5-hour drive from NYC.

• Thunder Ridge: Like Mount Peter, this is a small, entry-level mountain close enough to the city for a convenient day trip—perfect for little ones trying skiing for the first time. They offer a six-week ski program starting at age four, which is a standout feature since most programs begin at age five or six.

  • About a 1.75-hour drive from NYC.

If you plan to ski more than once this winter, rent your gear ahead of time rather than waiting in line at the mountain (truly, miserable with kids). I highly recommend arranging rentals in the fall, as many shops sell out by December/January. Buying skis at this age is usually not worth it, unless they can be handed down to younger siblings. We always rent skis, bindings, and boots and own everything else. Here are our favorite rental spots:

• Ski Barn in New Jersey (we always tack on a day trip to NJ with this one. You could add a visit to the American Dream Mall, which also has a ski mountain, Big Snow)

• Paragon Sports: Conveniently located in the city, there are options to rent new or used. Make a reservation ahead of time as they often can’t accommodate walk-ins.

• Sportiva: I haven’t been personally, but I’ve heard it’s an easy option on the UES.

Wow—there’s a lot of gear involved! We’ve tested and tried countless items, learned a lot the hard way, and here are the winners that have truly stood out for my kids…

• The number-one game changer for us was getting each of our kids a ski bag. It sounds simple, and I can’t believe it took us so long to do it. It keeps them organized and helps reinforce the personal responsibility we’re really trying to instill (they carry their own stuff)

• We tried about ten different variations of gloves or mittens for our kids and struck out each time until we landed on these. They’re more expensive than others but high-quality and worth it. These gloves are decent enough if you’re looking for an affordable option, but don’t have wrist straps like the Hestra ones. Whatever you do, do mittens not gloves. Gloves are miserable.

• For helmets, we’ve been really happy with the Giro brand—they’re snug, offer great coverage, and don’t shift around (and we get zero complaints about discomfort). Whatever you decide for helmets, just make sure it has a MIPS rating.

• For goggles, we also love Giro. They come in fun colors. Just do not forget the goggle cover or case, we learned the hard way on that.

• We’ve tried a lot of snow boots, and these have been the clear standouts. They’re easy to slip on, not too heavy or clunky, and tighten at the top to help keep snow out.

• For base layers I love Helly Hansen (you can tell the quality with this) and outer-layers, Helly Hansen is also excellent. I like Patagonia’s fleeces for mid-layers

• My kids love a neck gaiter and the Turtle Fur brand is our favorite. No socks brand has particularly stood out, but don’t think you can go wrong with SmartWool

• AirTags: We always leave a little AirTag in their pockets while they’re off at ski school. Who knows if it will actually do anything, but feels like the responsible thing to do.

• ….and finally, the HotHands! It’s best to stock up ahead of time, as they’re easily ten times more expensive on the mountain.

For true first-timers, here’s how my husband approached teaching our kids to ski: 1. Hire an instructor and book private lessons for the first few sessions—it’s a win-win for everyone. Trying to teach them yourself is back-breaking. 2. Keep it short at first (two hours max). Take breaks, keep it fun, and leave them wanting more. 3. Schedule lessons close together and consecutively so they can build confidence, momentum, and muscle memory. 4. Never, ever rent equipment on the mountain—do it ahead of time. 5. Hot chocolate bribes often work wonders

And here are the stand-out items my husband and I especially love for ski weekends:

• I’m a big winter bath gal and love a soak at the end of the day. These are the best bath salts. And if you really want to feel transported to the chicest lodge in the Alps, this bath oil is a must—it smells incredible and was one of the best gifts I gave my husband last Christmas.

• Dry skin gets real, and my forever favorite moisturizer is CeraVe—it beats all the fancy stuff. I stock up on tubs of it every winter for me and the kids. This is hands down the best lip gloss I’ve ever used; I’ve never found anything more effective for chapped lips.

• My husband can’t live without his TheraGun at the end of a big ski day.

• For snow boots these are excellent. And while not technically snow shoes, I love these On hiking boots that are waterproof, warm and I wear all the time in the snow and cold winter walks. For socks, I can’t live without these cashmere socks from J.Crew

That’s all I have for now, folks! I always love hearing from you—so feel free to reply directly to this email or leave a comment below. I’d love to know where you ski, products you love, and any tips you have for skiing with kids.