The Berkshires Travel Guide

USA  #7 in Best Weekend Getaways in New England

Courtesy of DenisTangneyJr/Getty Images

Free Things To Do in The Berkshires

Looking for free things to do? Here's our ranking of the best free activities in The Berkshires. Popular attractions include Monument Mountainand Herman Melville's Arrowhead Museum.
  • #3
    Things to do in The Berkshires
    View all Photos
    #3 in The Berkshires
    Hiking, Sightseeing, Free
    2 hours to Half Day
    Hiking, Sightseeing, Free
    2 hours to Half Day

    Follow in the footsteps of literary legends Herman Melville, Nathaniel Hawthorne and Oliver Wendell Holmes with a hike up Monument Mountain. Calling the town of Great Barrington home, Monument Mountain brims with history and striking views that overlook the Housatonic River Valley and Mount Greylock. Come prepared with your walking shoes and water – it takes some endurance to tackle the 720-foot elevation gain on the way up to Monument Mountain's 1,642-foot Squaw Peak.

    Outdoor enthusiasts who visit the Berkshires will appreciate the mountain's various trails, which range in difficulty. If you're looking for a leisurely climb up, take the Indian Monument Trail – a 1 1/2-mile path that climbs the west face of the mountain. For the most direct route, take the Hickory Trail, which measures less than a mile, but is considered the most strenuous. As you make your ascent, heed the advice of recent visitors and take in these views with a mid-hike picnic.

  • #9
    Herman Melville's Arrowhead Museum
    View all Photos
    #9 in The Berkshires
    Hiking, Museums, Free
    2 hours to Half Day
    Hiking, Museums, Free
    2 hours to Half Day

    Restored by the Berkshire County Historical Society, the home of "Moby-Dick; or, The Whale" author Herman Melville is open to visitors interested in learning more about the literary legend. Located in the historic town of Pittsfield, the house was inhabited by Melville from 1850 to 1863. Along with the home, visitors can tour the barn and surrounding grounds, which feature a farm and nature trail.

    Even some of Melville's biggest fans said they were surprised at the amount of new information they learned during their tours. Recent visitors appreciated the interesting stories shared by the site's knowledgeable tour guides, as well as the gift shop, which sells a variety of books about and written by Melville.

Explore More of The Berkshires

If you make a purchase from our site, we may earn a commission. This does not affect the quality or independence of our editorial content.


The 50 Most Beautiful Places in the World

Let these gorgeous destinations inspire you to travel more.

Holly JohnsonJanuary 16, 2020

50 Amazing Honeymoon Ideas

From relaxing weekend getaways to epic adventures, these honeymoon trips will help couples create memories to last a lifetime.

Kyle McCarthyJanuary 8, 2020

The Cheapest Days to Fly: A Guide to the Best (and Worst) Times to Travel

Use these tips and tricks to get the best deal on your next flight.

Lyn MettlerDecember 23, 2019

30 Top Florida Weekend Getaways

Spend sun-filled days exploring Florida's beautiful beaches, cities, parks and small towns.

Gwen PratesiDecember 9, 2019

The Best Travel Backpacks for 2020

U.S. News rated the best travel backpacks using recommendations from experts and consumers.

Lyn MettlerNovember 25, 2019

30 Top Wellness Retreats

Rejuvenate your mind, body and spirit at one of these relaxation-focused properties.

Kyle McCarthyNovember 21, 2019

30 Fun All-Inclusive Family Vacations

Book one of these all-inclusive trips that cover food, accommodations and activities galore.

Holly JohnsonNovember 14, 2019

5 Ways Cruise Lines Are Becoming More Environmentally Friendly

Industry considers impact as it looks to the future.

Gwen PratesiNovember 12, 2019

11 Unique and Quirky Cruise Destinations

Venture off the beaten path for an authentic cruising experience.

Christine SmithNovember 12, 2019

The 2020 Best Cruise Lines for Families

Gather up the gang and head out to sea with one of these six kid-friendly cruise lines.

Nicola WoodNovember 12, 2019