A Solo Female Travel Guide to a Weekend in The Berkshires/Pittsfield

I had first heard about the Berkshires from reality TV institution The Real Housewives of New York, by one Dorinda Medley. Maybe you’re familiar with her work? I just 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

Hotel on North

Where to eat and drink:

Tuna Tartare from Berkshire Palate
Brussels sprouts at District
Brioche burger from District
A brew and a view at Lift at Bousquet Mountain
Birthday cake flavored frozen yogurt from Ayelada
Grandma’s Pizza from Crust – I think this was my most favorite meal.
A brew from Hot Plate Brewing Co.

Things to do:

So many baby animals!
A mindful hike at Pittsfield State Forest with Berkshire Camino

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 🙂

One response to “A Solo Female Travel Guide to a Weekend in The Berkshires/Pittsfield”

  1. […] to Philly Finds. Quite a bit has happened since we last chatted. I traveled to Florida and to the Berkshires, and started a new job. It’s been a really exciting and fun time, and I’ve just really […]

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