The Berkshires, Travel, Uncategorized

Take a Holiday Stroll through Stockbridge, Massachusetts.

What is it about small town U.S.A?

They just get everything right. The charm of the people. The perfectly lined streets decked out ever so vividly for the holidays. Visions of yesteryear floating through your head instead sugarplums.

What are sugarplums?


The nearby town of Stockbridge, MA is perhaps center stage for all small towns. Nestled in the Berkshires, it is surrounded by foothills and with very little cell phone coverage. The perfect opportunity to take the day off and escape your distractions. Who needs a cell phone when you’re simply too busy admiring the town Norman Rockwell used to paint?


Perhaps one of my favorite artists, Norman Rockwell knew a thing or two about small town life. He knew the people, and how they looked and acted. He knew how to capture the essence like no one else ever could. He was small town life. With his studio centrally located above a diner in the middle of town, right along Main Street, he was able to capture it all from the second story window that overlooked the town.

During the holidays, Stockbridge is decked to the nines. The streets glisten with holiday magic as store fronts are draped in greenery and red bows as the the charm of the local townspeople captures every beat of your heart.

I promise they won’t give you a heart attack, however.


As you stroll through town, you’ll notice one very special place in particular; The Red Lion Inn. This stunning New England Inn on Main Street warms the souls of many. With its wide porch with classic rocking chairs, to its cozy interior complete with a crackling fireplace, The Red Lion Inn is sure to delight guests of all ages, especially those seeking a bit of nostalgia. It is perhaps a personal favorite of mine as I have spent many birthdays dining in the main dining room enjoying home cooked meals that are that of a five star restaurant.

Don’t get me started on the dessert.

If you seek out a town to escape to, even just for a day, Stockbridge is a treat, just like the rest of the Berkshires. It’s nostalgia complied with the warmth and joy of small town America speaks to the hearts of millions.

Don’t forget to check out the Norman Rockwell Museum while you’re in town.

Featured Image copyright of Ronald Ondrovic.


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