Berkshires Getaway

The Berkshires will always hold a special place in my heart. Located in Western Massachusetts near the borders of New York and Connecticut, it is a beautiful New England oasis with the perfect mix of cosmopolitan and countryside charm. At its center is the city of Pittsfield, where I did the majority of my medical school clinical rotations and intern year of residency training. It is also where I started this blog Daily Dose of Vita and began my content creation. Now, several years later, I had the chance to return for a summer getaway during the July 4th holiday and retrace my footsteps thanks to @lovepittsfield. The best part is I got to bring my dog, Westley, on his first roadtrip. Read on for some ideas to plan your next vacation:

Where we stayed

Hotel On North is a boutique hotel that pays homage to its 19th century roots through its preserved architectural features, from exposed brick and high tin ceilings to decorative columns and other characteristics that earned it a spot on the National Register of Historic Buildings.

Blending its heritage with modern designs created a welcoming and comfortable atmosphere complete with spacious rooms, cloud-like bedding, and for us, a perfect view of the downtown Independence Day parade.

Side note, I got to say hi to fellow pageant queen, Miss Massachusetts:

Hotel On North also has a restaurant downstairs called Berkshire Palate that we heard great things about but did not have a chance to try this trip.

As a dog mom, I especially appreciated how pet friendly this hotel was to its four-legged guests, offering complimentary water bowls and a dog bed for our stay (though Westley claimed one of the Queen-size beds as his own).

Where we ate

Our first night we were treated to dinner at the 101 Restaurant and Bar next to the newly renovated Holiday Inn & Suites. Highly recommend the Brussel sprouts and Burrata appetizer along with their macaroni and cheese.

They also had tons of vegetarian options. Afterward, we enjoyed an evening view of the mountains from the outdoor balcony.

The next morning, we stopped by Dottie's Coffee Lounge for cappuccinos and breakfast sandwiches. Fun fact, I wrote my first blog post for Daily Dose of Vita here. Check out the throwback photo below from way back when:

Writing my first blog post for Daily Dose of Vita all those years ago at Dottie's Coffee Lounge in Pittsfield, MA

It truly felt like everything was coming full circle! So crazy to look back and think of myself intern year sitting in this café wondering where I'll be as a physician and blogger.

Later, before we went to catch the play Cabaret, we got to check out the restaurant District Kitchen & Bar for dinner. I loved that everything was within walking distance. My favorite was their summer selection of handcrafted cocktails including this beautiful lavender drink.

I also ordered the Carne Asada Tacos, which were delicious.

Other great dining options in the area include:

• Methuselah Bar and Lounge (I used to come here all the time with friends when I lived here)
• The Marketplace
• Misty Moonlight Diner
• Flo's Diner

What we did

Boulder Rocks

If you find yourself in the Berkshires, take advantage of the natural beauty and go for a hike. Whether it's going to the top of Mount Greylock, traversing the Appalachian Trail (AT), or checking out the state park, you will find yourself surrounded by nature, lush greenery, and wildlife. We took a dog friendly trip to Boulder Rocks where they offered several different well-marked trails for all levels. We even ran into a through hiker on the AT who started his journey at the beginning of the trail in Georgia, has made it to Massachusetts and is headed all the way to Mt. Katahdin in Maine.

Hancock Shaker Village

We learned about the history of the Shaker community, took a tour of the land including the medicinal herb gardens (the doctor in me was so impressed), and checked out the iconic round barn.

Cabaret at The Barrington Stage Company Theater

The theater was conveniently located right next to our hotel. We caught an evening performance of Cabaret and it was incredible. The cast came together when the lead was replaced at the last minute by the understudy. All of them did a phenomenal job and now I want to watch the movie!

James Taylor at Tanglewood

A trip to The Berkshires is not complete without some live music. For me, one of the highlights was seeing James Taylor perform at Tanglewood - an outdoor concert venue that is also home to the Boston Symphony Orchestra. I had gone years before with my parents and it felt only right to return this year; honoring those memories while creating new ones.

The weather held out just in time for the fireworks display - the perfect way to end the night. And while we did not get to meet James Taylor, we did get to meet his saxophone player Lou Marini the next day!

Where we shopped

Connected to Hotel on North is the cutest gift shop called Dory and Ginger. They had a variety of work by local artisans and small business owners.

I picked up a pair of earrings that went perfectly with my medical presentation outfit later in the week. While visiting the area, I stopped by my former intern year hospital to pass on some of the knowledge I gained to the new resident physicians with a lecture titled "How to Succeed in Residency." It was wonderful to be able to give back to my program in this way. I even learned that they kept up the tradition I started of ordering jackets for all the residents each year. What a great legacy to leave behind!

For Tanglewood, we stopped by family-owned Guido's Fresh Marketplace to pick up our picnic spread. They had a huge selection of organic produce, charcuterie, cheeses, baked goods, and wine - all the fixings for a perfect evening on the Lawn.

It felt bittersweet to leave at the end of the week but I'm grateful for the opportunity to share my love for this beautiful area with all of you. Ending this post with a throwback to the first time I saw James Taylor in concert at Tanglewood with my parents.

I hope this post helps you plan your trip to the Berkshires. Let me know what you think!

Please note, this trip was hosted by @lovepittsfield