Themed Itineraries

Itinerary: Brooklyn

Advice for our hip, quirky, artsy friends.

The northern Berkshires is experiencing an artistic renaissance, and it’s the perfect escape for those looking for new experiences and a quiet “Brooklyn” vibe.

Check out concerts or performances at MASS MoCA such as Wilco, Bang on a Can, and stand-up comedians like Mike Birbiglia.

Stay at TOURISTS, a hotel and riverside retreat with a laid back vibe, excellent cocktails, and unique history and design. Or spend a weekend at Porches Inn, with retro-industrial architecture, cutting-edge technology, and a design sensibility that could be described as “granny chic.”

Visit Greylock WORKS and try a craft cocktail at Ski Bum Rum Distillery with gin and rum distilled on site. Check out our list of options below and explore the “hip” new culture in the Berkshires.


TOURISTS Welcome (hip hotel and riverside retreat)

The Porches Inn (boutique, 19th-century row houses, North Adams)

Maple Terrace Motel (Williamstown)

Coffee worth a (beautiful) drive:

Five Corners (Williamstown)
Six Depot (West Stockbridge)
Tunnel City Coffee (Williamstown and North Adams)

Amazing art and architecture:

MASS MoCA (North Adams)
The Clark (Williamstown)

Artisanal cheeses and grass-fed meats on the honor system:

Cricket Creek Farm (Williamstown)

Craft beers, kombucha, and more (yes, in a museum courtyard):

Bright Ideas Brewery (North Adams)

Authentic dive bar, local color:

Polish National Alliance (Adams)

Coolest roadhouse anywhere. Ask Bob Dylan and Joan Baez:

Dream Away Lodge (Becket)

Epic swimming hole:

Mt. Hope Park (Williamstown)


Sanford and Kid (lines around the block, 10am Fridays)

Berkshire Emporium (North Adams)

LOCAL Consignment & Boutique and Chapter Two Books (both in Williamstown)


Bands in a 19th century cow barn: The BarN
Vinyl at Belltower Records (North Adams)

Explore other itineraries:
Classic Williamstown Manhattan Busy Kids Foodies Outdoors