Ahhh, rest and relaxation! If you live in CT or around NYC, it’s a lot closer than you think! I love visiting the Berkshires in any season but there is something magical about it in the winter, particularly around the holidays. During the holidays the Berkshires turns into a real life Christmas village scene! You know, the ceramic houses that light up with the little people and fake snow? You have the classic looking post office, the bank, a church. My mom used to put up a whole display every year in a bay window and I loved pressing in the paper that made up the windows to reveal the light inside the house 😱Have you ever felt the material of the windows?! So satisfying. And speaking of the light inside, though the popular towns of the Berkshires are pretty small, there are vibrant scenes await you in each one if you know where to go (it is alive with energy).
The Berkshire town of Stockbridge was listed as the best Christmas town in Massachusetts according to Readers Digest where they published The Best Christmas Towns in America You Should Visit at Least Once. Another popular Berkshire town to visit, Lenox (10-15 minutes from Stockbridge), has a population of only around 5,000 people but this is what has always fascinated me about the Berkshires and keeps me coming back. For a place that feels so small, and it is, you open up the door to any of the restaurants at night, or Guido’s Fresh Marketplace during the day, and you find bustling little scenes. When we visited at the end of November, an in between time for tourism, we needed a reservation on a Monday night and we were almost turned away from two restaurants! So don’t let the size of the connecting the little towns fool you! A world of warmth and amazing meals wait for you behind each door.
Here is a list of what you can do during your Berkshire weekend getaway!
On the way: We drove up from CT and the Keystone Arch Bridge Trail in Chester MA was the perfect hike to stop on the way and walk around! The Keystone Arches are now a designated National Historic Landmark. If you want to walk the whole trail it is a total of 5 miles (2.5 in and out) with minimal elevation gain but even if you just walk in the first mile or so you’ll be able to see a couple of the big arches. A little history or the arches from this site: Along its length sit the first cluster of keystone arch railroad bridges built in America. They are wholly dry laid, range in height to 70 feet and made possible the longest and highest railroad in the world, the Western Railroad, in 1840.
Where we stayed: House on Golden Hill in Lenox
I loved this Airbnb in the Berkshires. The location is right outside the main little downtown of Lenox so it takes just 7 minutes to get to the restaurants, grocery store, and coffee shops. The owner is in another house on the property and he is so very attentive and helpful in orienting you to the area and the property.
-1BR, 1BA, pet friendly! 1790’s farmhouse property with newly finished wood floors, really the whole place has been completely updated while maintaining the original character of the structure. The property has lots of room for the dogs to roam and stretch their legs in the morning along with a stream and little bridge outside.
Book it: Visit their Airbnb site and send a message to Jared with the code Earlybird15 in order to get 15% off your stay all winter long! Hurry and reserve a couple cozy winter nights!
Where we ate: From living in the Berkshires for four years, I could make a whole list of my favorite places to eat but here are just a few!
Patisserie Lenox: The cutest authentic French pastry shop with more baked goods than you could ever try even if you lived there for years! Breakfast, sandwiches on fresh baguettes, homemade soup, and of course, coffee and tea. It’s a must try! You will love it, my favorite thing to get (which is probably why I haven’t tried every pastry yet) is a chocolate almond croissant, hello! You will not be disappointed.
Bistro Zinc: (In Lenox) This was my first time eating here and I really enjoyed it. You can tell everything is super fresh, lots of attention to detail in each dish. It has an upscale feel but I did not feel like I had to dress up or out of place when arriving in a comfy winter sweater and jeans.
Lenox Coffee: Stopped here in the morning before a hike. They have muffins and some other baked goods but no breakfast sandwiches, FYI. BUT, the lattes! Whew. Well, I got a coffee and honestly wasn’t crazy about it but Jared got a latte and it was really pretty amazing. I savored the little sips I snuck while he was driving to the hike. Next time I will get my own!
Where we hiked:
Wahconah Falls: When we came here on our second day it was super cold but fortunately it is only a 5 minute walk from the car to see the main falls! Great spot if you just want to wander around with a coffee and take some pics! This is over a half hour drive from Lenox but you get to drive through the larger town/city of Pittsfield which has the Berkshire Museum and tons of (more!) coffee shops and restaurants.
The Cobbles: This is only a 1.7 mile hike (out and back) but it has an elevation gain of over 700 feet. It does feel steep and is challenging but obviously it’s pretty short so it doesn’t last very long. Great views at the top! Faces west, I believe, so it would be a great sunset spot. You link up with the Appalachian Trail to get there.
Entertainment:
NightWood at The Mount (Edith Warton’s home), an outdoor sound and light experience! Loved doing this as it feels like a night hike except the paths are lit with little torches as you make your way to seven different scenes with lights and music. It truly is a peaceful experience and I would recommend it 100%. Cost: $20 for adults and $10 for kids 5 and up.
It’s about ¾-1 mile total for the whole experience and it took about 45 minutes – one hour for us. You go at your own pace and we stopped here and there to take pictures and videos. Dress warm!
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