Vacation in Massachusetts

In June and July, 2011, Tripfolio visited three areas of Massachusetts - Martha's Vineyard, the Berkshires and Boston. The 10 day trip was constructed around one special event at its core - the chance to see James Taylor in concert at Seijii Ozawa Hall at Tanglewood.

Why miss a chance to see two of our favorite places - Martha's Vineyard and Boston - again while we would be in the Berkshires for the concert anyway?  And why not do the entire trip with our best friends?  In this trip we achieved a perfect vacation balance of beach, mountain, and city experiences.

Martha's Vineyard

This was our third trip to Martha's Vineyard.  Our first visit - renting a house in 1999 with a group of good friends -convinced us we'd want to return one day.  Our second visit - in 2004, splitting our stay between Vineyard Haven and Gay Head gave us the chance to explore other parts of the island.

On this visit, we stayed at the Winnetu Oceanside Resort on Katama Beach. We sailed on a Black Dog tall ship, visited the Island Alpaca Company, explored Gay Head and Menemsha, focused on fine dining, but also just enjoyed some well-deserved beach time.

The Berkshires

This was the first time for any of us to see the Berkshires.  The drive from Martha's Vineyard to western Massachusetts went quickly, and our bed and breakfast in Lee, MA, the Federal House Inn, met all of our expectations.

We knew the James Taylor concert would be a highlight of this part of our trip, but we had left most of our time unstructued.  Our inn keepers gave us excellent advice; brochures at the inn gave us other ideas. The "Cottages" in and around Lenox, MA - summer homes of 19th century millionaires - are worth a return trip.  The Hancock Shaker Village in Pittsfield, MA was also a very welcome surprise.

Although we had been to Boston many times before, our friends had not. We decided to divide and conquer -they walked the Freedom trail, while we focused on new sights for us.

Our first "new" site was the Boston Public Gardens.  we'd never taken time to walk and enjoy the gardens.  Riding a Swan Boat was a highlight. Finding Revolutionary War re-enactors fighting a battle across the street in Boston Commons was an unexpected treat.

On our second day we saw the U.S.S. Constitution - Old Ironsides - explored the North End, and saw an amazing art glass exhibit of Dale Chihuly works at the Boston Museum of Fine Arts.