How to spoil your kids (and yourself) in the Catskills

There’s some serious magic in the Catskills. Memories from my first trip, with my wife years ago, include seeing a giant black bear just down the road from our campground and going a hike that totally bewitched us. We never give up on trails, but we ran into some sort of Rip Van Winkle voodoo on this one and, inexplicably exhausted, had to turn around before the payoff view.

Ever since then, the Catskills have loomed even larger in my imagination.

This summer we returned, though the vibe was altogether different: With two kids in tow, strenuous hikes up never-ending mountains were out. And in place of tents and bear-proof trashcans, our accommodations were the chic digs of Eastwind Hotel & Bar. But the magic? It remained. And the kids? Totally spoiled. Here’s how we did it.

1. Stay at a Scandinavian-styled boutique hotel.

Eastwind Exterior

Photo: Tamara Karram

Eastwind takes its name from its location on the east side of Windham, due west (and up) from the New York State Throughway via Highway 23. Remodeled and opened in 2018, there’s intentional style in every aspect of the property, from the tall, triangular eyes of the three lushna cabins that peek out from the back-lot trees; to the curving woodwork that frames the bar in the main building; to the tile in the bathrooms of the awesomely re-imagined, motel-esque rooms of the “Hill House” building (where we stayed).

I’m guessing your kids, though, aren’t easily impressed by thoughtful design features. Here’s what they will care about: the sturdy four-poster hammocks that can fit an entire family, the badminton and shuffleboard courts, the grassy slopes to run along and roll down, and the adorable border collie that chills in the common room. The crepes at the breakfast buffet ($20pp) won’t hurt, either.

Eastwind Hotel & Bar

Photos: Michael Greco, Tamara Karram

Note: My young family (kids aged 4 and 1) is probably not Eastwind’s primary demographic. There are no cribs available, and our room in the Hill House had no tub. But the staff didn’t bat an eye, and neither did any of the other guests. Turns out, folks here can get behind a little child-spoiling. Case in point:

2. Roast super-sized s’mores around the firepit.

Did I mention Eastwind has a communal firepit and provides Instagram-worthy Mason-jar s’mores kits, complete with telescoping roasting fork and the biggest marshmallows you’ve ever seen? Yeah, I’m pretty sure this is what my elder daughter will mention when we reminisce about the trip in years to come.

3. Take them on a Catskills hike that’s suited to their endurance and ability.

Catskills landscape

Photo: Michael Greco

Within a short drive, or even a short bike ride (cruiser bikes provided), of Eastwind are hikes that could keep you busy for a week or more. For older kids, there’s the opportunity to summit one of the Catskills High Peaks. Windham High Peak is accessible via multiple routes, including one in the Elm Ridge Wild Forest, right on Highway 23 about a mile east of the hotel.

Even if a trek like this (6+ miles round trip, with decent elevation gain) is beyond your little crew, hiking a portion of one of the trails will get you into gorgeous hardwood forest. We checked out the Elm Ridge Trail that starts at the end of Peck Rd, northeast of the village of Maplecrest, and followed it a mile or so up to the ridgeline. The 4-year-old was able to walk the whole way (with minimal dried-mango breaks).

But whatever you do, save a couple afternoon hours for the Windham Path, a 1.5-mile loop accessible from Highways 23 and 296. The flat trail winds through fields of wildflowers (laminated plant guides can be borrowed from the main trailhead) and along the Batavia Kill stream, complete with covered bridge crossing. Throwing stones into the water here was a close second to s’mores in the childhood memory category.

4. Treat them to a gourmet, family-style dinner.

My family’s bedtime schedule prevented us from taking part in Eastwind’s popular Saturday Night Dinner. Available for $50pp (add $18 for the wine pairing), these meals bring together hotel guests and in-the-know locals around a handful of communal tables in the salon (reservations required). I was able to pop in and sample the short rib (“recommended” is an understatement) and did see a family with tweens/teenagers in attendance.

Common room at Eastwind Bar & Grill

Photo: Michael Greco

Other tips and info

  • For both breakfast and dinner in town, we enjoyed The Windham Local. Live music Fridays and Saturdays.
  • The Catskills is a deceptively huge area, filled with cool little towns and incredible trails and views. What I’ve touched on here barely scratches the surface. Get out there and explore!
  • It’s also a year-round destination. We’re approaching fall foliage season now, and Eastwind would make an excellent base for a family ski trip in winter. Windham Mountain Resort is five minutes away, with Hunter Mountain 15-20. The bar has your apres covered, but my guess is the wood-barrel sauna is the place to be.
Sauna at Eastwind Hotel & Bar

Photo: Michael Greco

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