The Berkshires – A Weekend Getaway Travel Diary

I’ve been wanting to do a little travel diary/blog for a long time but haven’t gotten the chance to because of, well…quarantine, but with some of the state guidelines moving into different phases I was able to go to the Berkshires for a lovely weekend getaway and wanted to share what I did/saw/ate, etc.

First off, the Berkshires is famous for their summertime theater & music festivals. Places like Williamstown Theater Festival, Tanglewood, Jacob’s Pillow, Shakespeare & Company, Barrington Stage, and more have been drawing in the summer crowds for lots of artistic & cultural fun for years, but due to COVID-19 everything has been cancelled this summer, so it was very quiet and full of locals!

I’ve always wanted to go to Williamstown, Tanglewood, and Kripalu (a yoga/wellness retreat center also located in the Berkshires) but a little drive-by and looking at the empty grounds will have to do for now until we can all gather safely again.

The Berkshires are the perfect getaway if you love outdoorsy stuff. There are plenty of hiking trails, lakes, and mountains to ski in the winter time.


My friend and I drove from CT and was pleasantly surprised to find that we only live two hours away. We stopped in Great Barrington at Theory Wellness on the way to pick up some medicinal supplies (aka weed is legal in MA) and then went on our way to check into  our hotel.

We stayed at the Lenox Inn. It was very clean and quiet and had a nice pool that we swam at in the evenings, and was considerably cheap! (we each paid $120 for two nights)

We stopped for lunch in downtown Lenox at The Olde Heritage Tavern.

The vibe was nice, very tavern type foods. I got the veggie burger with curly fries and we shared a cocktail pitcher.

in Lenox, MA

Afterwards, we walked around and checked out all of the little shops. Most of them were open and they were very much “old lady type new england shops” if that makes sense to anyone… LOL. If you know, you know.

The rest of the evening we relaxed, swam in the pool, and enjoyed the sun.

Northern Massachusetts actually reminded me a lot of Northern California. The dry heat & weather felt the same & the fact you’re surrounded by mountains and trees and small towns!


Processed with VSCO with m5 preset
merm life playing in the pool 🙂


We started our day early because we wanted to get a hike in before it got too hot.

We stopped for breakfast and lattes before the hike at Shots Cafe in Lenox. I got an iced latte and the veggie burrito. It was super big and I couldn’t finish it all before the hike.


Then, we went on to hike Monument Mountain. There were two trails you could go on – one was only .60 miles but was the most strenuous. The other trail was 1.5 miles but was considerably less strenuous. We chose the longer and easier hike.


It ended up taking us about an hour and you felt like you got a really good workout in in parts.

There was so much beautiful nature surrounding us and so many cute mushrooms growing out of the forest, I couldn’t stop taking pictures of them!


like wow! that is a mushroom!! the earth is my favorite artist

On the way back, we took the shorter tail and there were parts where you were just walking straight down! We were both super grateful we didn’t take that way on the way up, because our longer trail was hard enough.

After hiking, we stopped to pick blueberries at Blueberry Hill Farm.


When I was a kid growing up in Pennsylvania, going berry picking in the summer time was our favorite family activity. Ever since moving to California, I’ve found there aren’t as many opportunities to “pick your own” at various farms, so it was so nice having this opportunity again in MA. Each person was required to pick 2 pounds (about $10) and it was really fun and rewarding to forage for our own berries.



After stopping back at the hotel to change and shower off from our hike, we explored the towns of Stockbridge and more of Lenox.

We went to lunch at The Marketplace and it looked super cute from the outside.


I was a little disappointed at the food (just not a lot and not worth the price) and the town of Pittsfield had more of a “big city” feel rather than the small, cute, quaint towns like Lenox and Stockbridge.

Stockbridge had a really cute general store where they were selling art & books from local artists. I picked up a book called “a grief sublime” from a local writer because I was super inspired by her form.


One change I noticed about myself since quarantine and all the change that is happening in the world is that I’m much more inclined to shop local when I can.

I never used to buy souvenirs when traveling, but now I wanted to support the local economy and support real, live people and small business rather than continuing to support big corporations like Amazon.

After doing some local shopping and stopping at The Lost Lamb Patisserie to get some delicious pastries for later (I got a strawberry shortcake and passionfruit macaron), we checked out Chocolate Springs Cafe and got iced coffee. I tried the iced coconut latte and it’s probably one of the most delicious coffees I’ve had in awhile.


There was a point in the day where we felt like we had seen and done everything there was to do and didn’t know what else to check out while we were there… it definitely felt like we had our fill and even though we were worried about only having one full day in the Berkshires, one full day was enough!

The rest of the day, we checked back into our hotel, got Jae’s Thai food for take out, relaxed, and swam and read by the pool.


Day Three

We had to check out of the hotel at 11 am, so we got up pretty early and cleaned up.

We stopped at The Main Street Cafe in Stockbridge to have breakfast.


After having our fill, there wasn’t much else we wanted to do or explore so we headed home and were home in just two hours!

It was the perfect little New England getaway.

I will definitely come bak to the Berkshires at some point to go to Kripalu since it’s been such a dream of mine, but until then I definitely recommend the Berkshires if you’re in driving distance!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s