Themed Itineraries

Itinerary: Outdoors

An insider’s guide to getting outside!

The Williamstown area is the perfect spot to escape from the hustle and bustle of city life and explore the outdoors. Traverse hundreds of hiking trails with unbeatable views, camp at wooded lakeshores,  engage with the great outdoors in a variety of inspiring ways.

Serious hikers might summit Mount Greylock, the highest point in the state, while more intermediate hikers might opt for the shorter Pine Cobble route for great views.

Try whitewater rafting and fishing on the Deerfield River or visit one of our great swimming holes to cool off on a hot summer day. Soak up nature with birdwatching at Mountain Meadow or a peaceful walk through the Berkshire Botanical Gardens.

We’ve curated a list of the best outdoor activities in the area, and we urge you to plan a visit to soak in the scenic outdoors!


Sperry Campground (Mt. Greylock)
Privacy Campground (Williamstown) tent sites and cabins, too.

Art in Nature:

Thomas Schutte’s Crystal atop the Clark’s Stone Hill (Williamstown) Challenge level: easy.

Easy walk through manicured pastures:

Sheep Hill (Williamstown) Challenge level: easy.

Butterfly and bird watching:

Mountain Meadow (Williamstown) Challenge level: easy.

Short, steep, and sweet hike:

Pine Cobble (Williamstown) Challenge level: moderate.

Panoramic views of the Hopper and the Greylock Range:

Stony Ledge (Williamstown) Challenge level: moderate.

The ultimate day hike (with food incentive):

Climb to the summit of Mt. Greylock for three-state views and a meal at Bascom Lodge. (Adams) Challenge level: hard. Dinner reservations required.

Climb, swing, float, and zip through canopies:

Ramblewild (New Ashford).

Epic Swimming Holes:

Mt. Hope Park, (Williamstown), waterfalls at
The Cascades (North Adams), the Tubs (Bennington)

Mountain biking:

Greylock Glen (Adams), Pittsfield State Forest (Pittsfield), Downhill Lift-served at Jiminy Peak (Hancock)


Raft, kayak, or inner-tube the Deerfield River with Zoar Outdoor (Charlemont) – check for dam release times

One of the best college golf courses in the world:

Taconic Golf Club (Williamstown)

Inspiring horticulture:

Berkshire Botanical Garden (Stockbridge), Bridge of Flowers (Shelburne Falls)

Explore other itineraries:
Classic Williamstown | Manhattan | Brooklyn | Busy Kids | Foodies