Over the river and through the woods

 Just past the New York State border into Massachusetts, The Red Lion Inn has welcomed travelers to the Berkshires since 1773, during the Boston Tea Party. A charter member of Historic Hotels of America and member of the New England Innkeeper and Resorts Association, and Original Historic Inns of New England, this 108- room inn lives up to its accolades. Berkshire County’s first convention of colonists expressing dissatisfaction with Britain’s policies of taxation without representation was held at the Inn just a year later. Other meetings to rebel against Britain also took place here.

Sitting in the downstairs pub and restaurant, the Lion’s Den, you can almost see these thoughtful men, brimming with insights and American ideals. The bar upstairs is also equally inviting and true to its historical significance, with a roaring fire just off to the side in the lobby. Staying at the Inn during the right season is also important, because you cannot stay or visit The Red Lion Inn without having a cocktail on it’s large, wraparound porch. Rock in a chair, cozy-up on a wicker lounge and take in the picturesque town of Stockbridge, Mass.

Once a pit stop for stagecoaches, tavern and Inn, for passers-by along the Albany, NY – Boston route, The Red Lion Inn quickly became popular and the center of village life where townspeople would gather.

In 1893 the Inn’s operation was taken over by Mr. Plumb’s nephew Allen T. Treadway, aided by his assistant James H. Punderson, whose daughter Molly later became the third wife of famed illustrator Norman Rockwell.

A handwritten thank you note and fresh flowers are a nice touch. Treats from Klara’s Gourmet Cookies (klarasgourmetcookies.com) is also a welcome for a hungry traveler

By mid-century, Stockbridge was discovered by wealthy families who came to escape the hustle-bustle and grit of city life. They built their weekend and summer homes, and with easier travel, Stockbridge was no longer a secret.

I could have done without the old baby portrait

above the bed – creepy!

Traveling alone, I was a little timid checking into the historic inn, for although I’m not too superstitious, I heard about the ghost stories coming out of rooms 301 and 312. Supposedly a friendly ghost likes to play pranks by touching guests and opening doors, but I needed a good nights sleep to face driving in the Nor’easter the next day. I was relieved and perplexed when my room was in one of the neighboring buildings that are converted guesthouses.

A great space to write, read and reflect

In a former private residence, across from a quaint, stone church, I had a two-room suite complete with a large bathroom that contained a claw-foot bathtub. After turn down service, don’t expect a chocolate on your pillow. Instead, the staff at The Red Lion Inn leaves bedtime stories at your bedside.

The Red Lion Inn does a great job with authenticity

One of my favorite Western Massachusetts towns is just north of Stockbridge. Started as a literary colony, Lenox, Mass. is now a bustling foodie town. One of the challenges of living in the Berkshires is a limited nightlife; even going to dinner at 8 pm can be a problem, but during this recent fall trip a friend and I stumbled upon Nudel (37 Church Street). This seasonally inspired restaurant was packed and worth the wait.

Dinning on Turnip and Arugula Soup (turnip latka and herbed goat cheese) with a side of Sourdough Toasts with olive oil was enough for a meal. Although the New York Riesling is probably more appropriate for warmer months, it was refreshing after a long day.

Published by

Michelle Glynn

Traded globe-trotting for motherhood. Side hustling as a freelance writer since 2001.

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