Family Fun

Winter Adventures

Safe and fun-filled ways to celebrate the season.

Looking for winter outdoor activities in Massachusetts? With  full moon hikes, cozy cooking classes, snowy owl prowls, fire pits, and more, this winter can be fun for everyone when you spend it with the Trustees.

No matter where you live, we’re ready to help you stay safe while enjoying everything that winter in Massachusetts can offer.

Northern Saw-Whet Owl

Owl Prowls

We are taking to the trails and dunes to see who-who-who might be out and about in the winter woods and dunes.
Family at a Fire Pit

Fire Pits

Reserve your fire pit—for a cozy picnic, date night, or family outing at some of our most iconic properties!
Fruitlands Sledding

Sledding Spots in Massachusetts

Bundle up and head out to these favorite sledding hills.
full moon

Full Moon Adventures

From Full Moon Hikes to Moonlit Meditations, you will find a nighttime experience to remember.
Two men cross country skiing at the Notchview

Skiing & Snowshoeing

Choose from one of many perfect winter spots for cross-country skiing and snowshoeing this winter.

Ski Notchview

Ski and Snowshoe Trail Passes will be available for purchase on October 1- Available to Trustees Members only.

Winter Hikes

Some of our favorite properties for a winter hike.
maple tap

Maple Sugar Events

When the sap starts running, the sweet treats are soon to follow. Join us for a delicious maple sugaring event!
hike at ward

Romantic Hikes and Walks

Whether you hike with your romantic loved one, family member, friends or yourself; the scenery is sure to make your heart go pitter patter.
More Winter Activities
castle hill family hike

Ideas for Hiking the Trustees

Curated lists and ideas for hiking Trustees properties.

Blues Clues: Helpful ways to stay positive this ...

We checked in with several Trustees staffers and asked them to share how they expect to counter the winter and Covid blues this season.

Family Fun

A variety of programs geared to get the whole family out! From snowy owl prowls, guided winter walks, to cozy fire pits, you are sure to find something

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