The Ultimate Guide to a Book-Filled Getaway in the Berkshires

Settled in the 1600s, the rolling hills of the Berkshires region of western Massachusetts are renowned for their natural splendor, untouched landscapes, and acclaimed literary history. 

In this vast expanse of land, you'll find the former homes of literary greats like Herman Melville, Nathaniel Hawthorne, Edith Wharton, and Henry David Thoreau, to name a few. The Berkshires are where many writers enjoyed summers together, gleaned inspiration, and authored some of their most well-known works.

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The Berkshires can create an intellectually stimulating and beautiful trip for New England book lovers or history buffs. Here's where to walk in the footsteps of the famous while creating your own story.

Great Barrington

W.E.B. Du Bois Childhood Homesite

A short drive from downtown Great Barrington, you'll find the site of the famed writer and civil rights activist W.E.B. Du Bois's ancestral home. While the house was demolished in 1954, the wooded land remains a historic area — it was in the Du Bois family for six generations.

On a walking tour, you can learn about the ongoing archaeological projects at the site and follow Du Bois's journey from the Berkshires to the world's stage. Just download or pick up the free brochure for the self-guided W.E.B. Du Bois in Great Barrington Walking Tour, and you'll come away with a deeper understanding of the places and people Du Bois connected with within the Berkshires.

Stay: The Briarcliff Motel

In Great Barrington, the pet-friendly Briarcliff Motel offers simple modern comforts (cozy common spaces, continental breakfast) with a bright and cheery aesthetic. It's located steps from Monument Mountain, where authors like William Cullen Bryant, Nathanial Hawthorne, and Herman Melville penned works inspired by the scenery. After paying a visit, gather around the motel's outdoor fire pit to enjoy a book or write your own tale under the night sky.


The Bookstore and Get Lit Wine Bar

Located in downtown Lenox, The Bookstore is one of the longest-running independently-owned bookshops in the region, drawing in locals and visitors for over 40 years. Stop in to grab a new read for the weekend and stay for a glass of wine — the Get Lit Wine Bar is right inside, giving you the perfect opportunity to unwind with your new purchase. You can also peek at the Shade Gallery, launched in the summer of 1976 for "the kinds of people who would come to a gallery that was inside a bookstore."

The Mount

Are you an Edith Wharton fan? Then, be sure to catch The Mount, the novelist's former summer estate that she considered her first natural home. Wharton designed the property, and she penned both The House of Mirth (1905) and Ethan Frome (1911) there. Today, the National Historic Landmark–the designated place is a cultural center and museum with several restored gardens. With a ticket purchase, you'll enjoy full access to the home, as The Mount forgoes velvet ropes and encourages patrons to sit in, interact, and be inspired by the space. Check The Mount's events calendar before visiting to learn about special programs, like staged readings and guided birding tours.

Stay: The Red Lion Inn

Located between Lenox and Great Barrington in nearby Stockbridge, The Red Lion Inn has welcomed travelers through its doors since 1773. Having hosted guests such as Hawthorne, Thoreau, Melville, and many presidents, The Inn is the perfect spot to drink in the area's history. Curl up with a good book in a velvet chair in the lobby, wander the halls and see if you can find the shoes of a famous starlet, or count teapots throughout the property (spoiler alert: there are over 200.) If you're an animal lover, watch for Norman, the inn's feline ambassador. He's usually curled up in a chair by the fireplace, the best seat in the house.



Drive north to the city of Pittsfield to tour Arrowhead, the family homestead of Herman Melville. Now a National Historic Landmark and home to Berkshire County's historical society, Arrowhead is where Melville wrote some of his most significant works, including Moby Dick. While the property is 20 miles from Mount Greylock, Melville could see the mountain right out his window — his description of the white whale in Moby Dick is said to have come from seeing the Berkshires' tallest peak covered in snow.

Stay: Hotel on North

Walk through the revolving door of this historic boutique hotel, a department store in a former life, and you'll find a mix of industrial-modern decor, local art, and gathering spaces perfect for reading or embarking on your own writer's retreat. The luxurious Library Suite is a literature lover's dream, with 125 shelves filled with books and art— it's even equipped with a rolling library ladder to let you access items out of reach.

Mount Greylock

Melville wasn't the only author to gain inspiration from the highest peak in Massachusetts. In fact, many writers of the time, including Oliver Wendell Holmes and Nathaniel Hawthorne, also explored the mountain. It's attracted the attention of more modern writers, too. In 2016, JK Rowling identified the summit of Mount Greylock as the site of the Ilvermorny School of Witchcraft--American's Hogwarts in her wizarding world. So while you won't encounter any sort of wand-waving spells, you will undoubtedly find magical views.


Chapin Library of Rare Books and Manuscripts

Located on the Williams College campus in a historic schoolhouse, the Chapin Library of Rare Books and Manuscripts contains a unique collection of books and documents from colonial times, including a final copy of the Declaration of Independence. To view materials, make an appointment for the Special Collections Weber Reading Room (which also offers picturesque views of the surrounding Berkshire Hills).

Chapter Two Books

Pick up a gently used book at Chapter Two Books in downtown Williamstown. All books here are donated, and the shop is managed by volunteers, with 100% of proceeds going to the Milne Public Library to support essential services and programming.

Stay: The Williams Inn

The Williams Inn prioritizes art and design in the heart of Williamstown, with contemporary interiors and architecture inspired by local area farms. The boutique property is also a short drive to Mount Greylock, so you're close to beautiful Berkshire views.