Jiminy Peak- A Winter Gem in the Berkshires

Jiminy Peak- A Winter Gem in the Berkshires

Tucked away in the northwestern corner of the Berkshires, Jiminy Peak Mountain Resort has been a tradition in my husband’s family since he was a young child. Upon my first visit to Jiminy Peak, it was easy to fall in love with the natural beauty of the mountain and the entire Berkshire region.  Jiminy Peak is the largest ski resort in southern New England offering its visitors over 40 trails to choose from. Quite noteworthy, it is the only mountain resort in North America that generates its own energy using alternative wind power, from their wind turbines. Currently, 100% of Jiminy Peak’s electrical demands are fulfilled through renewable measures; 66% provided by the Zephyr turbine alone.  

While Jiminy Peak offers all-year round activities, I am just going to be sharing (for now) our experience as to why we love it as a New England winter ski destination for the whole family. 

With 45 trails, 9 chairlifts on the mountain, there is the perfect trail for everyone. Novice to the elite, one can find themselves enjoying any of the beautiful groomed trails. At the base of the mountain sits the ski village, filled with a flurry of activity, a tavern, a brewery, a ski lodge food court, a ski shop, a kid’s care center, outdoor fire pits, a waffle & cider donut hut and so much more.  

At night, Jiminy Peak lights up in pure holiday fashion  for skiing every single night.   There is nothing quite like seeing the mountain glisten against the snow.

Whether you are looking for a day or weekend trip, Jiminy Peak is a great option for a memorable New England family ski trip.

For the Kiddos 

The mountain itself offers so much to do for the active family. My husband grew up learning to ski here and now we are watching our three-year old daughter learn how to snowboard on the same mountain.  We could not be happier that she is finding her love of winter sports at Jiminy Peak.

Kids Rule is Jiminy Peak’s signature kid’s program for those 3-14 years.  The all-day mountain camp offers the smallest skiers professional instruction and supervision.  Kids come together, make friends, enjoy learning all the basics and riding the magic carpet. Ski breaks for hot chocolate are a favorite for the littlest skiers before they head off to one of the fire pits for s’mores. 

There is also the Cubs Den Playroom, located at the base of the mountain.  The structured indoor play & care is available for those 6 months of age and older.  Reservations are required in advance, and lunch can be provided for an additional fee.  Rates are $15 an hour, per child *minimum of two hours.  

For the older kids or adults, who are just starting out, have a little experience but not yet ready to hit the trails, there is the Discover Zone.  Here, newbies can enjoy entry level terrain in a terrain-based learning program.  

For the Adults 

When you are done skiing, or even if you do not ski, there is plenty to do on or around the mountain.

Snow Shoe!

If skiing isn’t your thing, but you would still like to get some exercise and admire the gorgeous views, pop on your snowshoes and head out to the mountain! Snowshoes are available for rent at the Mountain Sports Shop located right in the village.  There are six miles of snowshoe trails, 3.5 of those miles being around the outer perimeter of the mountain.  

Runners, bring your sneakers!  The challenging hills and beautiful country roads around the resort make for some of my favorite scenic runs.


On Saturday’s, live music can be found at the tavern.  Pop in for a slope-side bloody mary or local craft brew.  Get cozy in one of the seats around one of the outdoor fire pits in the village and take it all in. 

Getting There

Located in Hancock, Massachusetts, in western Berkshire County, the mountain is nestled between the borders of Vermont and New York. With Mt. Greylock, the tallest peak in the state, just miles away and charming Williamstown, home of Williams College, down the road the area offers so much for visitors.  

Traveling to Jiminy Peak from most of New England could not be easier. It is just under three hours from Boston and New York City.  We make the drive from Fairfield County in Connecticut in 2.5 hours. Albany, NY is a short 45-minute drive.

Where to Stay

I am often asked where to stay at Jiminy Peak.  In full disclosure, I have not stayed at any of the properties I am listing here.  We stay at the mountainside home that has been in my husband’s family for years. There are several options on the mountain as well as hotels in the surrounding towns that I will list and link for you here below.  


On the Mountain

The Country Inn at Jiminy Peak –just a short walk from the trails, the Country Inn is on the property and offers Ski & Stay packages.  

The Wyndham Bentley Brook – are on-site condo units located on the property.

Check here for availability of homes and condo units on the mountain



Williamstown – 20 minute drive (one of my favorite northern Berkshire towns and home to Williams College). 

The Williams Inn – classic New England Inn, located in the heart of Willamstown, amongst the shops and restaurants.  The inn is built of stone and wood, it has all the feeling of a contemporary New England farmhouse. 64 contemporary farmhouse styled guest rooms. 

The Orchards Hotel – boutique hotel, timeless elegance, Modern style  

North Adams (located right next to Williamstown)

Tourists – *New – located in nearby North Adams, just 25 minutes away from the mountain is the new Tourists hotel.  Located along the Hoosic River in the revitalized town of North Adams, the new property is hip and offers “inspired by the great American roadside motor lodge”.  Modern design with all the natural feels of being out in the woods.

Fairfield Inn & Suites (Williamstown)

Other options: 

Pittsfield – 25 minute drive 

Hilton Garden Pittsfield 

Best Western Pittsfield 

Eating at Jiminy Peak 

The mountain offers several different options for dining on the mountain. 

 JJ’s lodge – your ski resort food court perfect for the family to grab a quick bite for lunch and some warmth

Christensen’s Tavern and John Harvard’s Brewery – both pub-like dining options mountainside

The Summit Lodge – Snacks and more found at the peak 

The Country Store – located right next to the main parking lot. A sweet little country market that will meet all of your needs.  Gourmet sandwiches and soups to go, salads and all other grocery necessities. 

Powder Hounds – located at the entrance of Jiminy Peak. Think country kitchen/winter pub. 


Other noteworthy dining in the area: 

Mezze Bistro & Bar 

Public Eat & Drink

Mill on the Floss

Water Street Grill 

Lantern Bar & Grill

Ioka Valley Farm Calf-A  (seasonal, Mid Februrary-April,  farm breakfast located 1/2 mile from the mountain)

Finally, sharing with you some of our favorite things to eat, do and see when up for a long ski weekend.  

  • An early reservation at Powder Hounds the first night we arrive.  We like to go with Pippa closer to 5 as it gets very crowded.  We always split the Shrimp Scampi Flatbread pizza. Powder Hounds is located at the entrance of the mountain. 
  • Start your day with breakfast sandwiches from the Jiminy Peak Country Store.  We love the country store.  They have pretty much anything you will need from homemade soups and salads to gourmet sandwiches, wine and an old-fashioned candy selection.
  • Drive for the burger.  During our last stay we drove 20 minutes to Pittsfield to the Lantern Bar & Grille. The burger was soooo good, we will definitely go again! 
  • Afternoon drive down to the Store at 5 Corners in Williamstown, about 8 miles from the mountain.  The Store at 5 Corners has the yummiest bakery and lattes when that 3 pm slump hits.  I will usually pick up wine here from their small but very good wine selection and some local cheese and goodies for our 5pm happy hours.  The store also has a variety of gifts from local artisans.  In the nicer weather, there is a wooden playground the kids love! 
  • Pancake breakfast at Ioka Valley Farm. This farm located less than a mile from the mountain offers a homemade farm breakfast. It is open mid-February (Presidents Day weekend through April).  You will not want to miss the pancakes, french toast and their very own famous maple syrup.  
  • My favorite place to grocery shop in the area is Wild Oats, co-op in Williamstown . We love to support the the local farmers and prefer their meats, dairy and produce.  I can not recommend their meatballs enough ( we usually pack our Yeti with frozen meats to bring home).
  • Make time for each other even if it is just a chair lift ride 🙂

Thanks so much for following along!  I hope to see you up on the mountain! If you have any questions about Jiminy Peak, please do not hesitate to reach out.



  • Toni West
    Posted at 13:02h, 07 January

    Loved this informative article, along with the great photos…

    It has inspired me to get a group together and check in for a few days this winter.

    • Stephanie Stellwagen
      Posted at 02:03h, 12 January

      Thank you so much!