Themed Itineraries

Busy Kids

Tips for moms and dads from moms and dads.

The Williamstown area is a wonderful getaway for families, with numerous outdoor and indoor activities for kids of all ages.

Embrace the outdoors with kid-friendly hiking at Hopkin’s Forest or up to Stone Hill Bench.

Ready to embrace your wild side? Jump over to Ramblewild, a tree-to-tree adventure park featuring several courses of varying difficulty. Find additional mountain adventures at Jiminy Peak every summer and winter.

Introduce your children to the arts — visit MASS MoCA and explore the Kidspace gallery where children can create their own art.

Whether it’s a long weekend in the summer or a ski getaway in the winter, we’ve curated the best activities, hotels, restaurants and adventures for children. Take a look below and create the perfect vacation for your family!


Air BnB (Northern Berkshire County)
Tourists Welcome (North Adams, outdoor pool, suites available)
Williams Inn (Williamstown)

Family-run, friendly meals:

The Log by Ramuntos (Williamstown)
Purple Pub (Williamstown)
Water Street Grill (Williamstown)
Capitol Restaurant (North Adams)

Ice cream worth the queue:

Lickety Split (Williamstown)

Art Mecca:

Kidspace & Sol Lewitt galleries, both at MASS MoCA (North Adams)

Music on the lawn:

Free Tanglewood rehearsals, summer Saturday mornings (Lenox)

Canopy adventures:

Ramblewild (New Ashford)

Baby animals and artisanal products:

Cricket Creek Farm (Williamstown)

Hancock Shaker Village (Pittsfield)

Blue tongue skinks and so much more:

Berkshire Museum (Pittsfield)

Out-of-this-world night sky:

Cloudy=Williams College Planetarium (Williamstown)
Clear= Cole Field (Williamstown)

Take a hike:

Easy=Cascades (North Adams)
Moderate=Hopkins Forest (Williamstown)
Challenging=Pine Cobble (Williamstown)

Awesome Playgrounds:

Williamstown Elementary School
Linear Park
Broad Brook Playground (at Harrison St and White Oaks Rd)

Winter Ski: 

Jiminy Peak (Alpine ski and ride, lessons available)

Prospect Mountain XC Ski (near Bennington, VT)

Explore other itineraries:
Classic Williamstown Manhattan Style Busy Kids Foodies Outdoors | Solo Trip | Southern Vermont