Finding the Good Stuff in the Berkshires (in the winter, with kids, during a pandemic!)

Written by:

Maia James


Updated: 09/29/2023

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After canceling basically all of our travel plans for 2020, we felt desperate for a mini vacation this Christmas. So I booked us a weekend at The Wheatleigh, a fancy hotel in the Berkshires that’s been on my wish-list forever.

What follows is a limited guide to a winter weekend in the Berkshires…with kids…amidst a pandemic. Feel free to post any questions or suggestion below if you’re considering, or have recently taken, a similar getaway!

Where to Stay in the Berkshires…with Kids…During a Pandemic…in the Winter

wheatleigh at night gimme the good stuff
Pulling into the Wheatleigh at night during the holidays is a charming experience.

We’ve traveled to the Berkshires several times before, since it’s less than three hours from our home in New York City.

We’ve previously stayed at the Red Lion Inn in Stockbridge, which is wonderfully old-school and has a particularly cozy bar, a good restaurant, and a gift shop your kids will love. Rooms during the winter months start at $335.

Red lion dinner berkshires
Pre-pandemic, we would often stay–and dine!–at the Red Lion in Stockbridge.

Last winter, when the Red Lion was fully booked, we get a room at the Wainwright Inn, which was a classic bed-and-breakfast and a short drive to Catamount Mountain, where we spent the weekend skiing. Rooms at the Wainwright start at $179.

This year, we decided to ski Butternut Mountain, and opted for the luxurious Wheatleigh for our accommodations. All four of us stayed in the Junior Suite with Balcony, with a king-sized bed and a daybed that they made up for us each night.

The Wheatleigh hotel berkshires

We really loved this hotel, and the kids kept saying that they felt like they were lords of our own manor. We never laid eyes on another guest, and the service was over-the-top personalized. The Weightleigh’s Covid protocols were also among the best I’ve found:

  • all out-of-state guests are required to present a negative test taken within the prior 72 hours;
  • everyone on-site is masked at all times–I appreciated that the staff’s masks fit over both their nose and mouth!;
  • the hotel was at half-capacity, and it has only 19 rooms to begin with;
  • all rooms were left vacant for at least 24 hours between guests.

The size of The Wheatleigh makes it an easy place to feel like you’re socially distancing while still being on vacation. The catch? Rooms start at $609.

Where to Eat in the Berkshires…with Kids…During a Pandemic…in the Winter

Indoor dining is open in Massachusetts, but we were still too spooked to partake. Luckily, we found Frankie’s in Lenox, just a few miles from our hotel.

The food is basic Italian-American, which is of course super kid-friendly; Wolfie took down an entire plate of clams and a massive serving of fried zucchini, pictured below. They had a nice cocktail menu and good IPA. Best of all, we had a little section of covered porch entirely to ourselves, complete with heat lamps.

fried zucchini berkshires
indoor dining wheatleigh berkshires

We actually DID brave the indoors for one lunch in the The Wheatleigh’s casual lounge–it felt safe because we were the only people there. It was a rare treat to eat without a puffy winter coat on, and they even provided a mask holder, which you can see in the photo below. My kids recommend the sliders, and I recommend the mesclun salad because Wolfie liked the dressing and ate a big bowl.

breakfast at wheatleigh berkshires

Many of our meals were eaten in-room at The Wheatleigh, and they were invariably excellent. Breakfast is included for all guests with a $15 “tray charge” if you opt to have it brought to your room rather than in the dining room downstairs. You can see from the photo below that breakfast options include smoked salmon bagel and all manner of eggs, and that meals come with veggies including asparagus and mushrooms.

What to Do in the Berkshires…with Kids…During a Pandemic…in the Winter

The Berkshires is probably our favorite “local” skiing destination, so that’s been the focus of our days most times. In the photo below you can see that the rentals building at Butternut was pretty empty and felt safe to me (all employees were masked and they limited the number of families allowed inside at once).

Butternut ski mountain berkshires
Felix Ski School Catamount
Normally, I am a big fan of ski school for my kids; pictured here is Felix at ski school at Catamount last winter.

In non-Covid times, we’ve enjoyed shopping in the charming towns around the Berkshires. The Norman Rockwell Museum is also worth a visit. And if you’re into beers or whiskey, Moe’s Tavern in Lee is a must–the photo below is of me there in 2019.

Mo’s Tavern Berkshires

Great Barrington is my personal favorite of the Berkshires towns, possibly because it reminds me a bit of my home town in Vermont (Montpelier). My kids love Robin’s Candy Store, which yes, is full of junky candy; it does have some old fashioned options like these chocolate covered almonds,

Robin’s Candy Shop Berkshires

The most enjoyable moments of the trip were spent on-site at the Wheatleigh, where Felix and I had a couple’s massage, we played games in the room, and enjoyed cocktails and hot cocoa fireside on the beautiful terrace. I’d definitely like to return in the summer and not during a pandemic, but even in this weird time, it felt like a much-needed vacation.

massages in berkshires wheatleigh
hot chocolate outsiden wheightleigh berkshires
games at the wheatleigh berkshires
berkshires wheatleigh

Maia, Founder & CEO

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