Weekend in The Berkshires

Stockbridge/Lee/Great Barrington, MA


The Berkshires is described as a rural region of western Massachusetts, though getting there is such a breeze! As long as you leave before 3 pm on Friday and avoid  Boston rush hour traffic, you can get there in just over two hours. That’s exactly what we did for this mini getaway trip. Quaint little towns are close to each other, so we covered Stockbridge, Lee and Great Barrington in the short visit. October is a popular time of year for tourists, especially from New York, since it’s practically their back yard. There is something for everyone- great restaurants, nice hikes, shopping, museums – I promise, you will not be bored!

View from the balcony at the resort

We went there with the goal to hang out with Sean’s parents, relax, eat good food and see the foliage of the nearby mountains. Foliage part was slightly disappointing- it has been a very warm fall so far, so many of the trees were still green. Regardless, we had a great time and accomplished more than we expected. We can always come back for more colors next year!


Based on a friend’s recommendations, we made dinner reservations at Chez Nous– charming French bistro in Lee, MA. It was delightful! IMG_2835We got the cheese and the pate plates to start. They went really well together! Restaurant offers half and full portions for the entree choices, which we loved. Both lamb and chicken half portions were plenty big after the apps, and left us just enough room for dessert 🙂 . Talking about dessert- get the Blondie Sundae with Sea Salted Caramel- it’s AMAZING! We were feeling adventurous and also ordered avocado ice cream that was one of their specials that night- it was not as impressive. Warm blondie, rum soaked raisins and vanilla ice cream is definitely the way to go!

 Lee is a cute little town to walk around and window shop.

We walked a bit before dinner and enjoyed the warm fall weather that we got so lucky with this weekend.

As I mentioned earlier, towns are close to each other, so we figured- why not check out the famous Red Lion Inn, located just a short drive away in Stockbridge, MA!

Established in 1773, the inn still holds its charm and welcomes travelers.

We were full from the early dinner, but I could not resist a glass of wine (ok, espresso martini as well…) while listening to the piano playing in the lobby and relaxing by the fire (there is an outside porch as well, if the weather is warm enough to enjoy). We were pretty tired from the work day and the drive, but if we had more energy, we would’ve stayed for the live band that plays downstairs at the Lion’s Den pretty much every night! Again, something to look forward to for the next time 🙂 .


No rush to get up early on this trip. We are taking it easy (not very typical of us 🙂 ).  Breakfast on the balcony, lunch at the Stockbridge Coffee and Tea cafe and we are off to the hike. Before I talk about that, let me stress how amazing this little coffee shop is. Connected to the old book store, it allows you to grab your coffee (or herbal chai tea, which was my favorite!) and read a book by the window.IMG_2737IMG_2738IMG_2740IMG_2742 We got ourselves a quiche each (try ham or broccoli/cheddar), followed by the soft oatmeal raisin cookie and that incredible chai ( I came back for another one on Sunday). It was light,  filling and it got us ready for the Monument Mountain!

We like to hike and we’ve done some pretty long trails, but this one was more for fun and for the foliage sights. You don’t have to be an experienced hiker to do this climb. It took us 90 minutes in a steady, but not rushed pace to do the loop. Located in Great Barrington, MA this is a popular reservation, so the parking lot gets pretty full. Some park on the grass around, we got lucky since the car left as soon as we arrived.  It’s $5 to park for the day. There are a few ways to get to the Squaw Peak (1640 feet). We chose the easy/low incline Indian Monument Trail up, which connected to the much steeper Squaw Peak Trail. Before going all the way up, make sure to stop by the Devils Pulpit for some pretty amazing views.IMG_2756IMG_2754IMG_2791 The summit is not that far away from there at all.

Even though it’s not a very exhausting hike, make sure bring some water/snacks- there are no facilities on the mountain. On the way down we took Hickey Trail- steepest and shortest way to the parking lot.

It was easy going down, but may have been a bit strenuous if we chose this way up. Not so much foliage as expected, but it was definitely fun early afternoon activity. I highly recommend the hike if you are in the area.

Twenty minutes and we are back to the resort. Shower, quick snack and lets get back to Great Barrington for a bit!

The town is simply lovely. Boutiques, cafes, restaurants- just bring your wallet 🙂 ! We enjoyed shopping, visiting a few art galleries and strolling up and down the main street. Definitely worth the visit! And we will be back soon enough- we have dinner reservations at the Allium- the restaurant with simple decor and great reviews!

Dare to order the Witchcraft cocktail- it’s delightful! The entrees were great (however, note to self- hen is a kind of mushroom, NOT a chicken! It was great hen risotto, despite the poultry we thought we were missing 🙂 ), but what we mostly enjoyed were the small plates. Golden, red, & chioggia beets, and crispy potato with avocado mousse were the crowd favorites.

There were not many dessert options available, so we chose to go across the street to Soco for a scoop of ice cream. IMG_2831Mexicali (or something to that extent) was slightly spicy (I believe it had some chili pepper in it), had a hint of cinnamon and kept the throat warm despite the cold treat- not for everyone, but if you like hot spices, you’ll most definitely enjoy it!



Last day of the mini vacation and we will spend it to the fullest. Just recently we started learning how to play tennis and this resort has beautiful tennis courts with no one in them! That will be our first activity for the day. Followed by the swim in the pool and relax in the Jacuzzi. Ok, now that we feel awake and energized, lets go see Sean’s favorite artist  at Norman Rockwell Museum!

Located in Stockbridge, MA it presents the worlds largest and most significant collection of Rockwell art.

Norman Rockwell – 20th century author, painter and illustrator with world famous Golden Rule painting and numerous cover illustrations for the Saturday Evening Post. It cost $20 per person to get in, but I can say it’s totally worth it. Visit Rockwell’s studio that was moved there as the museum moved locations as well. It has his authentic furniture and you can see the simple surroundings where the incredible art was born.

A pretty productive day so far, right? IMG_2882Now we just squeeze in a mini golf session right near hotel and go get dinner before driving back to Boston. For this we chose authentic Mexican cuisine- Xicohtencatl Restaurant located in our favorite- Great Barrington, MA.


We got in without any reservations, but soon after the place filled up.  Fun decor, big patio with cozy string lights, but most importantly- strong margaritas and delicious food!

We went with Guacamole (of course!), Carnitas and Tres Salsas Enchiladas- portions were generous and everything tasted delightful. Now only if we didn’t have the two hour drive back home 🙂 !


Short as the weekends always are, this trip packed a lot of fun and activities. We love long exotic travels, but that’s simply not reality working five days a week from the office. What I hope this post tells you is that short trips can be very exciting too! Simply changing the scenery, getting outside, visiting new town can be very relaxing and rejuvenating. It rewires the brain, lowers stress and brings you back to work with more ideas and optimism. It keeps you going until another weekend, so you can explore again 🙂 !

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