Winter Outdoor Activites Massachusetts - The Trustees of Reservations

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Eleanor Cabot Bradley House during Winterlights

Winter Adventures

Safe and fun-filled ways to celebrate the season.

Looking for winter outdoor activities in Massachusetts? With dazzling light shows, full moon hikes, cozy cooking classes, reindeer quests, 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.

Winter Events

Winterlights at The Stevens Coolidge Place

Holiday Stroll

The Stevens-Coolidge Place welcomes you to a family-friendly Holiday Stroll & Festive Parade of Trees this holiday season!

Castle Hill Illuminated

Experience the magic of the Winter Solstice as a multi-sensory experience in the landscape.

Full Moon Adventures

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

More Winter Activities

Saturday, January 16

Saturday, January 16

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Saturday, January 16

Saturday, January 16

Frozen Fruitlands

Fruitlands Museum | Harvard

Join us this winter at Frozen Fruitlands for safe winter fun: Hikes, Snowshoeing, Sledding, Fire Pits, Exhibitions, and more!

Saturday, January 16

Saturday, January 16

Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

SOLD OUT! Please see other dates for newly added capacity.

Saturday, January 16

Saturday, January 16

Open Barnyard at Weir River Farm

Weir River Farm | Hingham

SOLD OUT

Saturday, January 16

Saturday, January 16

Private Fire Pits at Frozen Fruitlands

Fruitlands Museum | Harvard

Get outdoors with family and friends this winter and warm up with private Fire Pit bookings at Fruitlands Museum.

Saturday, January 16

Saturday, January 16

Winterlights at Naumkeag

Naumkeag | Stockbridge

SOLD OUT for the season.

Saturday, January 16

Saturday, January 16

Winterlights at the Bradley Estate

Eleanor Cabot Bradley Estate | Canton

SOLD OUT for the season.

Sunday, January 17

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Sunday, January 17

Sunday, January 17

Winter Weekends at Appleton Farms

Appleton Farms | Hamilton & Ipswich

With so much happening and lots to do, winter is a great time to be at Appleton Farms.

Sunday, January 17

Frozen Fruitlands

Fruitlands Museum | Harvard

Join us this winter at Frozen Fruitlands for safe winter fun: Hikes, Snowshoeing, Sledding, Fire Pits, Exhibitions, and more!

Sunday, January 17

Snowy Owl Prowl at Crane

Castle Hill on the Crane Estate | Ipswich

SOLD OUT! Please see other dates for newly added capacity.

Sunday, January 17

Brickyard Open House

The Brickyard | Chilmark

Welcome to the Brickyard!

Sunday, January 17

Sunday, January 17

Brickyard Open House Hike

The Brickyard | Chilmark

SOLD OUT! Hike back in time! SOLD OUT!

Sunday, January 17

Sunday, January 17

Winter StoryWalk on the Trails (daily)

Chestnut Hill Farm | Southborough

Come visit our farm's StoryWalk®, an innovative and delightful way for families to enjoy reading and the outdoors at the same time.

Sunday, January 17

Sunday, January 17

Reindeer Quest! (throughout January)

Chestnut Hill Farm | Southborough

Get the family outside to discover our elusive herd of wooden reindeer, found throughout the farm's trails!

Sunday, January 17

Mindful Winter Wander

Castle Hill on the Crane Estate | Ipswich

Start your day with a physical and mental breath of fresh air!

Sunday, January 17

Sunday, January 17

South Shore Reindeer Quest

Weir River Farm | Hingham

Complete one or all five Reindeer Quests at Trustees reservations around the South Shore.

Sunday, January 17

Private Fire Pits at Frozen Fruitlands

Fruitlands Museum | Harvard

Get outdoors with family and friends this winter and warm up with private Fire Pit bookings at Fruitlands Museum.

Sunday, January 17

Winterlights at Naumkeag

Naumkeag | Stockbridge

SOLD OUT for the season.

Sunday, January 17

South Shore Reindeer Quest

Weir River Farm | Hingham

Complete one or all five Reindeer Quests at Trustees reservations around the South Shore.

Sunday, January 17

South Shore Reindeer Quest

World’s End | Hingham

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Sunday, January 17

South Shore Reindeer Quest

Norris Reservation | Norwell

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Sunday, January 17

South Shore Reindeer Quest

Two Mile Farm | Marshfield

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Sunday, January 17

South Shore Reindeer Quest

Whitney and Thayer Woods | Hingham and Cohasset

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Sunday, January 17

Fire Pit Picnic at Appleton Farms

Appleton Farms | Hamilton & Ipswich

FIRE PIT AVAILABLE 4-6

Sunday, January 17

Sunday, January 17

Castle Hill Hike

Castle Hill on the Crane Estate | Ipswich

Love the Crane Estate?... Have we got a hike for you!

Monday, January 18

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Monday, January 18

Monday, January 18

MLK Jr. Day Family Explore the Shore

Cape Poge Wildlife Refuge | Chappaquiddick Island

Chappy MLK Jr. Day!

Monday, January 18

South Shore Reindeer Quest

Weir River Farm | Hingham

Complete one or all five Reindeer Quests at Trustees reservations around the South Shore.

Monday, January 18

South Shore Reindeer Quest

World’s End | Hingham

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Monday, January 18

Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

SOLD OUT! Please see other dates for newly added capacity.

Monday, January 18

Frozen Fruitlands

Fruitlands Museum | Harvard

On Holiday Mondays this winter, we are happy to offer special Monday grounds-only hours to our Frozen Fruitlands Admission.

Monday, January 18

South Shore Reindeer Quest

Norris Reservation | Norwell

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Monday, January 18

South Shore Reindeer Quest

Two Mile Farm | Marshfield

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Monday, January 18

South Shore Reindeer Quest

Whitney and Thayer Woods | Hingham and Cohasset

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Tuesday, January 19

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Tuesday, January 19

South Shore Reindeer Quest

Weir River Farm | Hingham

Complete one or all five Reindeer Quests at Trustees reservations around the South Shore.

Tuesday, January 19

South Shore Reindeer Quest

World’s End | Hingham

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Tuesday, January 19

South Shore Reindeer Quest

Norris Reservation | Norwell

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Tuesday, January 19

South Shore Reindeer Quest

Two Mile Farm | Marshfield

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Tuesday, January 19

South Shore Reindeer Quest

Whitney and Thayer Woods | Hingham and Cohasset

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Wednesday, January 20

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Wednesday, January 20

Winter StoryWalk on the Trails (daily)

Chestnut Hill Farm | Southborough

Come visit our farm's StoryWalk®, an innovative and delightful way for families to enjoy reading and the outdoors at the same time.

Wednesday, January 20

Friends on the Farm: Winter Afterschool Series

Powisset Farm | Dover

Kids, come join us for an afternoon on the farm, cook in our kitchen, explore the trails and much more!

Wednesday, January 20

Wednesday, January 20

Private Barnyard Tours at Weir River Farm

Weir River Farm | Hingham

Visit the Barnyard this winter at Weir River Farm.

Wednesday, January 20

South Shore Reindeer Quest

Weir River Farm | Hingham

Complete one or all five Reindeer Quests at Trustees reservations around the South Shore.

Wednesday, January 20

South Shore Reindeer Quest

World’s End | Hingham

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Wednesday, January 20

South Shore Reindeer Quest

Norris Reservation | Norwell

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Wednesday, January 20

South Shore Reindeer Quest

Two Mile Farm | Marshfield

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Wednesday, January 20

South Shore Reindeer Quest

Whitney and Thayer Woods | Hingham and Cohasset

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Thursday, January 21

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Thursday, January 21

Reindeer Quest! (throughout January)

Chestnut Hill Farm | Southborough

Get the family outside to discover our elusive herd of wooden reindeer, found throughout the farm's trails!

Thursday, January 21

Thursday, January 21

Winter Warmers Garden Mixology Class

Boston Community Gardens | Boston

Mix up complex cocktails featuring foraged ingredients like spicebush and hickory nuts in our take-home virtual mixology class.

Thursday, January 21

South Shore Reindeer Quest

Weir River Farm | Hingham

Complete one or all five Reindeer Quests at Trustees reservations around the South Shore.

Thursday, January 21

South Shore Reindeer Quest

World’s End | Hingham

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Thursday, January 21

South Shore Reindeer Quest

Norris Reservation | Norwell

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Thursday, January 21

South Shore Reindeer Quest

Two Mile Farm | Marshfield

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Thursday, January 21

South Shore Reindeer Quest

Whitney and Thayer Woods | Hingham and Cohasset

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Friday, January 22

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Friday, January 22

Fire Pit Picnic at Appleton Farms

Appleton Farms | Hamilton & Ipswich

Gather around a cozy fire for a perfect winter picnic at Appleton Farms.

Friday, January 22

South Shore Reindeer Quest

Weir River Farm | Hingham

Complete one or all five Reindeer Quests at Trustees reservations around the South Shore.

Friday, January 22

South Shore Reindeer Quest

World’s End | Hingham

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Friday, January 22

South Shore Reindeer Quest

Norris Reservation | Norwell

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Friday, January 22

South Shore Reindeer Quest

Two Mile Farm | Marshfield

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Friday, January 22

South Shore Reindeer Quest

Whitney and Thayer Woods | Hingham and Cohasset

Complete one or all five Reindeer Quests this winter at Trustees reservations on the South Shore.

Saturday, January 23

MLK, Jr. Walk (self-guided)

Francis William Bird Park | Walpole

Come to Bird Park to learn some lesser known and intriguing facts about MLK Jr.

Saturday, January 23

Castle Hill Fire Pit Adventure

Castle Hill on the Crane Estate | Ipswich

Take a hike and explore the grounds and then warm up around a campfire.

Saturday, January 23

Winter Weekends at Appleton Farms

Appleton Farms | Hamilton & Ipswich

With so much happening and lots to do, winter is a great time to be at Appleton Farms.

Saturday, January 23

Fire Pit Picnic at Appleton Farms

Appleton Farms | Hamilton & Ipswich

SOLD OUT

Saturday, January 23

Frozen Fruitlands

Fruitlands Museum | Harvard

Join us this winter at Frozen Fruitlands for safe winter fun: Hikes, Snowshoeing, Sledding, Fire Pits, Exhibitions, and more!

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.

Full Moon Adventures

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

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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