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Take a Walk Back in Time

Posted on June 02, 2018Written by Lindsey Schmid

By Kim Ostellino

The Berkshires is truly a unique travel destination offering visitors unparalleled scenery, amazing outdoor activities, non-stop cultural events, and vibrant downtowns full of trendy shopping, diverse restaurants, and lively nightlife. Now, more than ever, folks are seeking out the Berkshires for its historic sites, to learn more about the pivotal role that our county played, in the shaping of America’s history.

Bring your history buff boo! Location: Arrowhead in Pittsfield

You wouldn’t think that the Massachusetts Whale Trail would lead you as far inland as the Berkshires, but Arrowhead, in Pittsfield has earned itself a spot on this self-guided tour that brings you along the coastline, with stops at museums, area attractions, and historical sites. One of America’s preeminent authors, Herman Melville, lived in a modest farmhouse on the outskirts of Pittsfield. It is here that Melville was inspired by the snow-covered Mount Greylock in the distance (which reminded him of a whale) to pen the iconic novel, Moby Dick. Visitors can tour the grounds and home, and look out the same window that he did when he wrote the novel.

Come for the experience.The southern Berkshires is experiencing a bit of Hollywood this year, as one of the area’s most prominent figures, Elizabeth Freeman (also known as Mum Bett) is being featured in a soon to be filmed box office movie, based on the book by local author, Jana Laiz. Visitors can tour a portion of the Upper Housatonic Valley African American Trail, with a stop at The Ashley House in Sheffield. Not only is this the oldest house still standing in the Berkshires but you can see firsthand how Mum Bett worked and lived, before winning her court case, freeing her from slavery.

The Bidwell House in Monterey offers visitors a look back at life in early Colonial days. This home, which is a New England Heritage Site, was once a thriving dairy farm and in later days it became an art school, before being restored to its original appearance, with well-appointed furnishings of the period. On July 7, there will be a Country Fair at the Bidwell House. This free celebration is open to the public and will offer live music, tasty food, fun for the kids, demonstrations and garden tours.

Most of our historic sites are open seasonally, so if you are planning on adding in some local heritage to your Berkshire trip, make sure to visit their websites, which will keep you up to date on daily hours, and special events. Make time for history on your next trip to the Berkshires, you will not be disappointed.


Kim is a freelance writer, devoted to bringing the best of the Berkshires to locals and visitors alike through her website, Berkshire Girl Online. She is an avid hiker and kayaker, who also loves to explore the cultural and historical sites of the Berkshires.

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