Berkshires Winter Get-Away: Catamount + Great Barrington

Berkshires Winter Get-Away: Catamount + Great Barrington

We love the Berkshires – what’s not to love? Known as a haven for both nature and the arts, this beautiful, yet low-key vacation destination is popular year round. Located in western Massachusetts, towns and villages dot this mountainous and scenic region. If you’re into the outdoors, take your pick – there are limitless activities, including skiing, the main focus of this particular post. If you’re into the arts, some of the country’s most renowned art institutions are here, including MASS MOCA, The Norman Rockwell Museum, the Clark Art Institute, The Eric Carle Museum of Picture Book Art, and more. The culinary scene here is great too, with many of the restaurants farm to table. About 2 ½ – 3 hours from New York City, what more could one want from a get-away that includes culture and outdoor beauty?

This post will highlight Catamount ski mountain, which is one of three ski mountains in the Berkshires; the other two are Ski Butternut and Jiminy Peak. Catamount is located on the border of New York and Massachusetts (technically in Hillsdale, NY), and 15 minutes away from Great Barrington, MA, a popular Berkshires town filled with good restaurants, antique shops, quirky book stores and vintage finds.

On a recent weekend we decided to ski at Catamount with a friend who often goes there. My girls are relatively new skiers, and we have been taking them to the same mountain since they started (Mt. Peter ), which we love, but is very small. My friend suggested Catamount because it’s a nice size for families. It’s not too small, but definitely not too big where you lose your kids. And it’s also convenient. From where we live it’s 2 hours away – a perfect distance for a weekend away, or even an overnight, which is what we did.

You may also enjoy: Why We Love the Swiss Hutte inn: Cozy and Affordable Berkshires Escape

Catamount Ski Mountain

We loved Catamount, and here is why. It’s a family run ski mountain and extremely family-friendly. All the staff were super nice, and the lift operators were great and always made sure to pay extra attention to those with younger kids. And the most fabulous thing about it was – there were no lines! I asked my friend and she claimed it’s always this mellow. I’m sure on holiday weekends and school vacations it gets crowded, but on an ordinary winter weekend it is crowd and stress-free.

And the size was perfect, with 36 trails and a good combination of green, blue and black levels. It was our first time on a quad chairlift, which goes up the entire mountain, and for my girls a brand new experience. At the top of the mountain, as well as throughout, you have beautiful views of the Berkshires below and surrounding. The trails were for the most part in good condition, and thanks to the help of their snowmaking capabilities, most of them were open.


ski lessons at Catamount mountain

We signed the girls up for their popular ski school program called Mountain Cats (ages 4-12), which seemed to be well-run and organized. We chose their half-day program, which is 2 ½ hours long, with a hot chocolate and snack break halfway through. My girls said they liked their instructors and had a fun time. Mountain Cats afforded us the time to go out and ski ourselves sans-kids, and take in the whole of the mountain, going down some of those slopes the girls wouldn’t dare. If 2 ½ hours is too long for your kid(s), or your kid(s) are younger, they have Private Lessons, Group Lessons (ages 5 and older, 1 ½ hours), and Tiny Tot Lessons (private lessons for 3 and 4 year olds).

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The rest of the time we skied with our girls, covering a lot of trails without it being too overwhelming for them. At the end of the day I recommend hitting the Tavern for a drink, located in the main ski lodge, before heading out for the evening. Overall, Catamount is a completely do-able mountain with a good vibe and very friendly. For more information, such as ticket and lesson pricing, see their website here.

Catamount ski mountain


We found an adorable ski cottage in Hillsdale, NY through AirbBNB (just look at the pics!) that was of great value and perfect for our group. It was about 15 minutes from the mountain.



Other lodging options include:

Swiss Hutte, which is super convenient and right at the base of the mountain, and with a very good restaurant. Route 23, Hillsdale, NY, 12529. (518) 325. 3333

Hotels and motels recommended by the mountain, the majority in Hillsdale and Great Barrington. See list here.

You may also enjoy: Stockbridge, MA: Wintertime in the Berkshires

Great Barrington: Dining + Shops

As for town-life and shops and restaurants, Catamount is close to Great Barrington, MA, an attractive and happening town set in the heart of the Berkshires. It has main street charm and a plethora of shops, ranging from artisanal cheeses to gourmet ice cream to toy stores to vintage clothes to unique book stores to outfitters to home décor to very good restaurants. It’s a vibrant town with its own distinct flavor. We really enjoyed strolling around and dipping into so many great stores. If you want to dine out in Great Barrington, the restaurants below come highly recommended:


Baba Louie’s, 286 Main Street, 413.528. 8100 – this is definitely a tourist attraction, but for good reason. The pizzas, with their unusual combinations, are delicious and not too heavy. And their salads are insane. Get their “group” salads – enough to feed 5 people!

Barrington Brewery & Restaurant, 420 Stockbridge Road, 413.528.8282 – post-skiing and snow tubing at a brewery? Sounds about perfect.

Prairie Whale, 178 Main Street, 413. 528.5050 – hear it’s amazing New American. We are definitely going here on our next visit.

Naji’s, 405 Stockbridge Road, 413. 528.5540 – Lebanese, which may be tough to take the kids to, but good food.

Bizen, 17 Railroad Street, 413.528.4343 – If you want sushi (my girls like California rolls), this is the place to go.

Martin’s Restaurant, 49 Railroad Street, 413.528.5455 – Contemporary American, another one for the list.

Xicohtencatl, 50 Stockbridge Road, Route 7, 413.528.2002 – delicious Mexican that has been recommended by a few different people.

Great Barrington MA

And for dessert, SoCo Creamery, 5 Railroad Street, and Robin’s Candy Shop, 288 Main Street, for ice cream and candy. This is one of the best candy stores I’ve ever been to – and anyone who knows me knows I LOVE candy!

For a relaxing ski weekend get-away in a beautiful setting where you feel like you’ve put the week behind you, go to Catamount for some skiing, and hit up Great Barrington for some shopping and dining.

You may also enjoy: A Guide to Jiminy Peak




  1. Lyn Cook
    February 6, 2016 / 3:07 pm

    Sounds Great ! Lots to do,if weather is not so good.

  2. February 6, 2016 / 4:17 pm

    Corey, Love your site–will e mail Pat Whitman’s address as well–she’d love to follow you.
    Have spent lots of summers in the Berkshires and it’s one of my favorite spots besides Maine.Let me know when you might come to the city.Would love to see you.Your girls are so special. with love, Lindsley

    • February 6, 2016 / 5:08 pm

      Thanks so much, Lindsley, and great to hear from you. Would be nice to catch up. Are you still with the Contemporary Arts Council? If so tell everyone hi. Miss you all. xox

    • February 6, 2016 / 6:54 pm

      Ha – just laughed out loud.

  3. Jessica
    February 7, 2016 / 1:42 am

    Great weekend and fantastic write up!!

    • February 7, 2016 / 3:27 am

      Thanks for a great weekend, we’ll do it again!

  4. February 7, 2016 / 4:16 pm

    Sounds like a great place – you’re so lucky you can be somewhere like this and skiing in 2 hours drive, very jealous!! The kids ski school sounds perfect too and no lines – well that is just heaven….. Love the cottage too, it looks so cozy!

    • February 8, 2016 / 12:06 am

      Yes, it’s great we have good skiing so convenient..but we don’t have other countries right next to us like you all do!

  5. February 8, 2016 / 8:04 pm

    Air BnB can really deliver sometimes. And what a great location. I’ve only been to America 3 times but I long to return.

    • February 9, 2016 / 3:12 am

      I need to make it over your way too. Yes, Air BnB can be a god-send.

  6. pigeonpairandme
    February 8, 2016 / 9:38 pm

    I like the range of different ski courses there are for youngsters at Catamount. We’ve just taken ours to an indoor slow slope for the first time, and it was great watching them slide around on skis. Good tip about AirBnB. We’ve used them in Europe, but never in your neck of the woods before.

    • February 9, 2016 / 2:58 am

      I’m so curious about indoor skiing – I read your post a while back and have been intrigued ever since!

  7. February 9, 2016 / 2:03 am

    What a great selection of things to do and see for a short “ski” weekend away.

    • February 9, 2016 / 2:59 am

      Thanks Sally – yes, a lot can be packed in in this part of the country for skiing. Thanks for stopping by ;).

  8. afamilydayout
    February 15, 2016 / 3:21 pm

    I clicked on this post as I live next to the county of Berkshire – in the UK! It’s quite strange reading about a different place with the same name. That candy store looks much better than anything in the UK Berkshire though 🙂 #Mondayescapes

    • February 16, 2016 / 4:29 am

      Too funny! That happened to me recently when I went to read someone’s post – thought it was the U.S. and it was the UK..was a pleasant surprise! Thanks for reading :).

  9. February 15, 2016 / 4:33 pm

    This looks fabulous and I love the sound of how arty the place is too. I especially love that first photo with the snowy land and bright blue skies – such a gorgeous combinations!
    (I also thought this was going to a post about the UK too, like the comment above – haha!) #Mondayescapes

    • February 16, 2016 / 4:31 am

      Ha – maybe I’ll accidentally get more UK bloggers coming to my site!;). Yes, the sky was so blue that day, made especially bright against the snow. Thanks for reading!

  10. February 23, 2016 / 2:43 pm

    This is such a lovely place for a skiing break! I totally understand why you love it.
    I would be very afraid of the chairlift haha!
    Great idea to suggest where to stay, eat and shop. Nice cottage you guys had with Airbnb 😀
    Thank you for linking up with #MondayEscapes 😀

  11. February 24, 2016 / 1:27 am

    Thank you! A lovely post! I was reminded that I’ve heard that James Taylor song a million times and never seen the actual “Berkshires,” so, again thank you!

    • February 24, 2016 / 5:56 pm

      Glad you liked it and thanks for reading!

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