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Traveling Massachusetts: The Berkshires!

This is one in a series about touring Massachusetts and Newport, Rhode Island. My husband and I spent three weeks there in October, 2021. This Travelogue is a journal of our trip, done for my own sake and to show readers why you should visit Massachusetts.

The Stockbridge Country Inn

We stayed five nights in the Berkshires area of Western Massachusetts, in the small town of Stockbridge. There is much to see and do in the Berkshires and all the towns are fairly close together, so we decided it would be easiest to explore from one place. There are many B&Bs to choose from, but I am so glad we chose the Stockbridge Country Inn.

The Stockbridge Country Inn, photo from their website.

According to their website, the Stockbridge Country Inn is a Federal country house dating from 1856. It’s many bedrooms and suites are filled with beautiful, yet comfortable, antiques. We stayed in a suite called The Maids Luxury B&B Suite. It was a beautiful, cozy place to stay, especially when the rain was falling. And each morning we had a delicious country breakfast served by friendly staff.

Vern and Diane are the proprietors of the inn. They are a wonderful couple. Vernon – at 99 years old – is a living legend: a WWII veteran who fought in the Pacific, parachuting behind enemy lines. Vern was on the same USS Missouri battleship as General MacArthur when the general, on Sept. 2, 1945, accepted the surrender of Japan.

My husband with Vernon and Diane of the Stockbridge Country Inn

Vern is as sharp as ever, though you might not get a chance to realize that with his garrulous wife around. But on two different occasions, I purposely waited until she’d left the room, then I had great conversations with him. With the help of staff, Diane and Vern run a wonderful B&B–I highly recommend it.

Downtown Stockbridge

Downtown Stockbridge is very cute, but can get a little crowded during “leaf-peeping season.” Except for having to wear a mask, I loved exploring the cute stores and restaurants. Mostly we enjoyed walking around outside, taking in the sites. One day we drove up in the hills and saw many large and gorgeous homes. We were told that most of these homes are owned by wealthy Wallstreet-New-Yorkers who buy them as a second home. That makes sense because there isn’t much industry in the small towns of the Berkshires!

Because of traffic, downtown Stockbridge doesn’t look as quaint as Norman Rockwell’s depiction, though the buildings haven’t changed much.
See if you can find the matching buildings in the Rockwell painting.

A Halloween Story Walk

I loved the Stockbridge Library, at least from the outside. Due to covid, it wasn’t opened. However, they set up a wonderful story walk for Halloween. I’d like to copy their idea sometime.

Laminated pages from a book were posted along a path through the library’s garden.

Halloween displays were interspersed throughout.
I’m going to steal this idea for next Halloween!

The Red Lion Inn and Restaurant

We ate a delicious (and non-budget) dinner at the Red Lion Inn. The inn is a town landmark and would probably be a great place to stay–just know that they are still operating under covid restrictions. I prefer the Stockbridge Country Inn myself.

You can read about the Red Lion Inn’s history here.

The Stockbridge Cemetery

One afternoon I walked to the Stockbridge Cemetery and got there in time to take a few snapshots at sundown. I would have liked to explore it more, but darkness was falling fast. You can read more about the cemetery here.

Stay tuned for my next blog about the Norman Rockwell Museum in Stockbridge. And if you want to go back to the beginning of my series on Exploring Massachusetts, start here. Thanks for reading!

A Headless Horseman highlights this home in the nearby town of Lenox.


  1. Anonymous Anonymous

    Brings back wonderful memories!

  2. Anonymous Anonymous

    Thanks Karen great job. Enjoyed reading blog and seeing your photos. Always excellent. Tish

    • KarenGough KarenGough

      Thanks so much Tish. Glad you enjoyed it!

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