I had first heard about the Berkshires from reality TV institution The Real Housewives of New York, by one Dorinda Medley. I can’t write this post and not mention Blue Stone Manor. Phew – I’m glad I got that off my chest and spoke my truth.
From what I had seen on TV, I envisioned the Berkshires to be charming, idyllic, and a hell of a good time. And my recent visit to the town of Pittsfield in the heart of the Berkshires proved all of those assumptions to be true. A weekend in the Berkshires is perfect for a romantic getaway, girl’s weekend, or a solo trip like I did. However your trip might be, you’ll find everyone you meet to be so friendly and welcoming.
When my trip happened, it was the weekend before I began my new job and jumped into a new industry, after leaving my job of 9 years. I had been feeling both excited and understandably nervous, and also I felt restless. I couldn’t have been in a more perfect setting to reset my mind and prepare for this new chapter of my life.
SO below are all of the things I did around the Pittsfield area. Other nearby attractions include the Red Lion Inn, Tanglewood, Herman Meville’s Arrowhead, the Clark Art Institute, and Jacob’s Pillow.
Disclosure: These experiences were complimentary, all opinions are my own
Where to stay: Hotel on North
- Address: 297 North Street, Pittsfield, MA 01201
- In walking distance to many restaurants, and a short driving distance to many local attractions.
- Spacious, beautiful rooms.




Where to eat and drink:
- Methuselah Bar and Lounge
- Berkshire Palate
- Misty Moon Diner
- District Kitchen & Bar
- Hot Plate Brewing Co.
- Dottie’s Coffee Lounge










Things to do:
- Spend an afternoon at Hancock Shaker Village
- Have guided, mindful hike with Berkshire Camino
- Visit Pittsfield State Park



Inspired by her solo pilgrimages on the Camino de Santiago, a 500-mile walk across Northern Spain, founder Mindy created Berkshire Camino. Her walking and hiking tours are designed to empower guests to choose how much they want to be challenged – it’s a very attainable approach, and you are encouraged to be open about your curiosity along the trails.
The solitude of nature. The freedom of being able to scream into the forest without fear – it was so FREEING. If you are into nature, spirituality, mindfulness – this is a MUST DO.



Where to shop:
And there you have it! I hope if you’re planning your summer weekend getaways now, you’ll consider adding the Berkshires to the list 🙂
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