What a year. Full of hardships, heartache and buzz words like “unprecedented,” “new normal,” and “abundance of caution.” But as silver linings go, coupled with the universal closures of the entire world, it left one thing open — the outdoors. A place that happens to be our favorite place of all, and a place that we were lucky enough to enjoy to the fullest. 

We had set a goal to do 50 hikes & we went way beyond that, doing over 65 hikes in 2020!

We did some challenging hikes, revisited some old favorites and experienced other trails in seasons we hadn’t experienced before. This year we saw Berkshire Family Hikes blurbed in a local newspaper and magazine, organized a successful trail clean up, featured in a recurring column on Berkshires Macaroni Kid, reached 1000 followers on Instagram and was suggested by some of you asking for hiking recommendations. Thank you all for your tremendous support over the past few years! I can’t tell you how wonderful it feels!

Heading into 2021, I’ve never been more excited for the possibilities. We have a website revamp on the horizon, a GIANT list of hikes to tackle, and the workings of a book are starting to come together!

We are also excited to be participating in the 52 Hike Challenge and encourage you to join us!

Keep scrolling to see some of our favorite hikes from 2020!


Favorite Hike

The Pines
High Street, Dalton

Biggest Challenge

Lye Brook Falls
Manchester, VT.



Old Mill Trail
Route 8, Hinsdale

Beyond the Berkshires

George Aiken Wildflower Trail
Bennington, VT.

Favorite Waterfall

Glendale Falls
Clark Wright Road, Middlefield

Best Meltdown

Constitution Hill
Bridge Street, Lanesborough



Pittsfield State Forest
Cascade Street, Pittsfield

Summer Hike

Chapel Brook Falls
Williamsburg Road, Ashfield



Shaker Trail
Route 20, Hancock



Dorothy Frances Rice Wildlife Sanctuary
South Road, Peru

Favorite Moment

Monk’s Pond
Richmond Mt. Road, West Stockbridge

Mom’s Most 


Diane’s Trail
Gould Road, Monterey