History Buff Trip Ideas

The human history of this region is deep and engaging. Learn about the original residents, the Revolutionary War, agricultural advances, factory life, a railroad tunnel, artistic innovations, and much more.

What we may call the northern Berkshires and southwestern Vermont are the ancestral homelands of the Mohican and Abenaki peoples. Before Europeans, indigenous communities had already been inhabiting the region for at least 12,000 years.


To learn about some of the earliest European settlers and the forming of Williamstown, visit the Williamstown Historical Museum. Look into an historic barn, study artifacts, and enjoy a children’s discovery room, plus festivals, talks, and tours.

Take the self-guided Williamstown History Walk.

Visit the 1753 House in the rotary park. And, immerse yourself in the history of the town and Williams College with one of Dustin Griffin’s informative tomes.

Throughout the 19th century, Williamstown farmers logged much of the forest to establish farms. The landscape became pastoral grazing grounds for sheep and cattle plus bountiful fields of crop. Learn more at Sheep Hill and Hopkins Forest.

North Adams

North Adams grew during the industrial revolution to include a fabric dyeing factory that supplied uniforms for the Union Army, then an electronics manufacturer. Both factories were located in the buildings that now house contemporary art at MASS MoCA.

While you’re in North Adams, take a stroll down Eagle Street to get a feel for what the town looked like in the 19th century. Today you’ll find the street bustling with new vintage shops, galleries, and eateries. To learn more about the history of North Adams, pick up a book by Joe Manning.

Mount Greylock

Mount Greylock Visitor Center

At 3,491 feet, Mount Greylock is the highest point in Massachusetts. At the top you can explore 90 mile views, the Veterans War Memorial Tower, and Bascom Lodge. The lodge and the Thunderbolt Ski Shelter were built by the Civilian Conservation Corps (CCC).

Learn more about the historic ski racing trail at the Thunderbolt Ski Museum in Adams.

Hoosac Tunnel

To the east of Mount Greylock, the Hoosac Tunnel is a railway that burrows almost five miles through the Hoosac Mountain Range from North Adams east to the town of Florida. Construction began in 1851 and finished in 1875. Over those 24 years, around 200 men died, giving it the nickname, “The Bloody Pit.”

Bennington, VT

A short drive north from Williamstown, Bennington Museum presents and explores the rich culture of the region in all its forms, from the 18th century to the present. Explore the largest public collection of Grandma Moses’ paintings, a 1924 Martin Wasp touring car, modern and contemporary art exhibits, lectures, music, and more.

The Bennington Battle Monument commemorates The Battle of Bennington that took place on August 16, 1777, widely considered to be the turning point in the Revolutionary War.

A quick elevator ride takes you up about 200 feet to the observation deck, where you can soak up incredible views of three states: Massachusetts, Vermont and New York.

Come, uncover the rich history of these beautiful lands!

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