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 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!
Two people in a Trustees kitchen putting spoonfuls of filling on dough to make ravioli

Cooking Classes

The Trustees teaching kitchens have a wide range of classes for all ages and skill levels designed to help you boost your culinary game.
Two children on a sled downhill surrounded by snow with a farmhouse, trees, and blue sky in the background

Sledding Spots in Massachusetts

Bundle up and head out to these favorite sledding hills.
Moose Hill Farm Trail

Outdoor Adventures

Guided hiking, mountain biking, and kayaking adventures at Trustees properties that are truly hidden gems.
full moon

Full Moon Walks & Hikes

From Full Moon Hikes to Moonlit Meditations, you will find a nighttime experience to remember.

Snowshoeing

Choose from one of many perfect winter spots for snowshoeing this winter.

Ski Notchview

Notchview is located in Windsor, MA and renowned for its Nordic skiing and snowshoeing.

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!
Two people viewed from the back walking hand in hand down a path in the middle of a sunny field

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.

Winter 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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