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A weekend in the Berkshires

A weekend in the Berkshires

The Berkshires is easily my favorite weekend escape from New York City, mostly because of how relaxing and laid-back it is. I swear my big city anxiety melts away the minute I breath in that fresh country air! And unlike many weekend destinations close to the city, there’s barely any traffic to get there and it’s not exorbitantly priced.Prospect Lake in the Berkshires

We spent the weekend there with David’s parents and his sister and her fiancé (I suppose I can officially start calling them my in-laws!), and it was just as lovely as always (see: my first time there, on video and Gert’s first time). We did all of our standard favorite things at this lovely little lakehouse—canoe rides around Prospect Lake, plenty of s’mores around the campfire, long walks down quiet roads—and added in a few new things, like a 1000-piece puzzle or a game of chess on a rainy day.

In other highlights: I opted to leave my makeup at home and not to turn my phone on for a full 24 hours, which was SO SO SO freeing. Instead of checking in on social media or keeping up with some crazy text chains or trying to create an Insta-worthy makeup look, I curled up and read Encyclopedia of an Ordinary Life, and dedicated myself wholeheartedly to a crazy intense puzzle. This is actually something I’m trying to incorporate on every trip: intentional time without makeup or my phone to give myself a bit of a break.

The Red Rooster in Brewster, New YorkThe Red Rooster in Brewster, New YorkThe Red Rooster in Brewster, New YorkThe Red Rooster in Brewster, New York

Our first stop, as always: Red Rooster! This little hamburger drive-in place is a road trip favorite. I never miss the opportunity for a cherry dip, and Gert was very enamored with the cheeseburgers.

Farmers market in Hillsdale, the BerkshiresFarmers market in Hillsdale, the BerkshiresFarmers market in Hillsdale, the Berkshires Farmers market in Hillsdale, the BerkshiresFarmers market in Hillsdale, the BerkshiresFarmers market in Hillsdale, the Berkshires

We popped over to the flea market and farmers market in Hillsdale one morning, which was just lovely. The main highlight was ALL OF THE DOGS: Gert made so many new friends! Although I’m not usually much for flea markets, I did love the farmers market: there was the cutest flower stand, an incredible shop of homemade pickles, a man blowing enormous bubbles to entertain all of the adorable children, and someone entertaining us all with folk-country tunes on a guitar.  The only thing I regret is contemplating too long over whether or not I should get a cinnamon sugar croissant—by the time I decided, yup, I want that, they were all sold out!

The Old Mill in Egremont, the BerkshiresThe Old Mill in Egremont, the Berkshires

We also had dinner one night at The Old Mill, which is a lovely restaurant in Egremont. As wonderful as the meal was, though, I have to admit: my favorite meals in the Berkshires are always the ones we make at home! It’s so fun to have a grill and a bunch of fruit and veg picked up from the farmers market, and to enjoy it with a few beers and a lake view.A weekend in the Berkshires with Gertie the pug A weekend in the Berkshires with Gertie the pug  A weekend in the Berkshires  A weekend in the Berkshires with Gertie the pug

Although we did have a few outings this year, most of our time is just spent enjoying the our perfect location on Prospect Lake. Weather was a little chillier than past years—we are having the coldest start to summer out here!—but we still had a nice time canoeing, playing croquet, and taking a quick dip in the lake.

A weekend in the Berkshires with Gertie the pug

And of course, working on Gert’s swim skills! Even though she’s a natural, we still picked her up a puggy life vest.

The only bummer: I got hit with a very terrible stomach flu on our last night, which forced me out of commission for most of our last day there. Luckily, it was rainy, so I don’t feel like I missed out on TOO much, but it’s still been a rough 48 hours for me. And honestly, another reminder to always travel with Pepto-Bismol tablets–I swear, you only need them when you don’t have them!

Zagg keyboard in the Berkshires

That said, it was still such a lovely weekend and I can’t recommend this little slice of bucolic paradise enough. Have you been to the Berkshires before? What’s your favorite part? 

This post was typed on my ZAGG keyboard.