I’ve traveled the world, but never to the Berkshires in Massachusetts and so I let a concert in Tanglewood and the Food and Wine Extravaganza be my reason to spend a weekend away.

How did I pull this off and how did it go? Here’s how I handled the key challenges on this trip and what I learned.

Challenge 1 - Hotels were on the pricey side.
I decided to try Airbnb. I found an affordable room in Pittsfield in the home of two realtors and from the description and photos provided my gut told me that this was the place for me. It was economical and would afford me some company.

Challenge 2 - What other events and attractions to visit?
My strategy was daytime activities in towns a distance away, but evenings spent in the town I was overnighting. I visited the Mount (Edith Wharton House and Garden) the Norman Rockwell Museum, three Berkshire Fringe performances, the local farmers market in downtown Pittsfield, the Tanglewood Food and Wine Extravanza, listened to a free rehearsal in Tanglewood and attended a Boston Pops orchestra concert.

Challenge 3 - Where would I eat?
On my first day I brought my lunch with me so that I could eat anywhere. I picked up dinner in a local speciality supermarket and had a picnic in the backyard where I was staying. On night two I had a late night meal following a theatre performance in a Tapas Bar which was lively and one of the few places that stays open until midnight. Day three I attended the Tanglewood concert with a Meetup Group and we picnicked on the lawn at the venue.

Challenge 4 - Who would I meet?
My first stop was The Mount.  I asked two ladies heading to their car about their visit. I learned that I could easily forego the formal tour and spend the time gained enjoying the gardens.   In that quick chat I also learned they were from the Midwest and that visiting the Berkshires was a dream come true. What a happy beginning for my trip - hearing that. 

I had a nice discussion with my B&B host when I arrived and had a nice conversation with the theatre troupe at the Berkshire Fringe. At the wine tasting, I networked with a Meetup Group member from CT who helped me navigate the event. It was easy meeting new people at that event by sharing tables or sharing tips.    

During my second evening at the theatre I chatted with a number of fellow theatre goers. As a part of the small intimate theater, the cast conversed with the audience before the performance. The next day I attended the Tanglewood concert with members of a Meetup group. There were a number of opportunities to strike up conversations before and after the concert.

Challenge 5 - How would I feel?

By mixing the types of places I attended, I was able to create a nice flow of quiet time and dialogue. I visited the Farmer’s market on day two to meet locals. I paced myself by returning to my B&B in the late afternoons to rest before heading out for evening activities.  Mostly I felt happy to be on an adventure and I felt proud of the small milestones I passed as the trip progressed.

What I learned?
I covered what I set out to cover, but an additional night would have permitted a swim in a lake and to explore some hiking trails. I didn’t have the opportunity to attend a Jacobs Pillow performance (my host said it was magical) and will make that a priority for a future visit.

A B&B was the perfect place to stay to get tips from a local and feel a part of the community. In this town, I should have allotted spending more time at the Farmer’s market because it was truly a community hub.

I did more research than usual ahead of this trip because it was a short trip and time was precious. My research included the housing market as a possible discussion point with my host. My efforts were worth it.

There were some nice commonalities with some of the people I crossed paths with.  For example, I met a couple who shared a hometown with me and a fellow visitor who had experience organizing a travel Meetup group.  

Even though my approach was on the frugal side, the costs totaled about $500 for a 3 day, 2 night getaway. Accommodations $182, Tickets $204 , Meals $65, Fuel $40. I brought a food cooler with me with a stock of beverages and that worked out well. Being a part of a Meetup group activity at Tanglewood on my last day was a nice “grand finale”.

I totally recommend solo travel to the Berkshires. I returned happy, energized and proud of what I accomplished.  For me a key bit of the choreography was really engaging in the new surroundings which includes the people there.