Guided Hikes

Hiking trail with fern understory at Slocum's River Reserve

Guided Hikes

Guided hikes for explorers of all abilities.

We have guided hikes for explorers of all abilities, you’ll get to discover the beauty of special places around Massachusetts. All with a trusted guide.

From sunrise and full moon hikes to explorations for families, owl prowls, or hikes to get your heart rate up — you’ll find the guided hike and outdoor adventure that’s perfect for you.

Saturday, November 23

Saturday, November 23

CraneOutdoors: Sunset Hike to Cedar Point

Castle Hill on the Crane Estate | Ipswich

Join us as we explore this hidden gem of the Crane Estate at sunset!

Saturday, November 23

Wolly Hudsonia on Castle Neck (photo credit T. Barrieau)

Saturday, November 23

CraneOutdoors: Castle Neck Hike in the Dunes

Crane Beach on the Crane Estate | Ipswich

Ever wonder what's in the dunes behind Crane Beach? Some of the North Shore's best hiking is waiting for you to explore.

Saturday, November 23

Saturday, November 23

Native Plant Walk & Milkweed Fiber Spinning

Appleton Farms | Hamilton & Ipswich

Learn about plants important to indigenous culture and how to harvest and spin milkweed fiber on this educational outing.

Sunday, November 24

CraneOutdoors: Sunset Hike to Cedar Point

Castle Hill on the Crane Estate | Ipswich

Join us as we explore this hidden gem of the Crane Estate at sunset!

Sunday, November 24

Sunday, November 24

Bird Watching Exploration on the Belle Isle Marsh

Belle Isle Marsh | Boston

Bird Watching Exploration on the Belle Isle Marsh

Friday, November 29

Friday, November 29

Celebrate Green Friday at Fruitlands

Fruitlands Museum | Harvard

Embrace Green Friday by exploring the beautiful Fruitlands grounds—free access from dawn to dusk for hiking, relaxing, and enjoying nature!

Friday, November 29

Friday, November 29

CraneOutdoors: Celebrating Indigenous Culture Dune Hike

Castle Hill on the Crane Estate | Ipswich

Join this hike about the history and culture of Pawtucket and other local tribes and how archaeologists study our special places.

Saturday, November 30

CraneOutdoors: Sunset Hike to Cedar Point

Castle Hill on the Crane Estate | Ipswich

Join us as we explore this hidden gem of the Crane Estate at sunset!

Saturday, November 30

Saturday, November 30

CraneOutdoors: The Castle Hill Hike

Castle Hill on the Crane Estate | Ipswich

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

Sunday, December 1

Sunday, December 1

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Sunday, December 1

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Sunday, December 1

Sunday, December 1

CraneExplorer: Coastal Holiday Crafts

Castle Hill on the Crane Estate | Ipswich

Join this interactive education program to learn about treasures found on the beach and make your own coastal holiday crafts!

Saturday, December 7

CraneOutdoors: Sunset Hike to Cedar Point

Castle Hill on the Crane Estate | Ipswich

Join us as we explore this hidden gem of the Crane Estate at sunset!

Saturday, December 7

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Saturday, December 7

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Sunday, December 8

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Sunday, December 8

Sunday, December 8

CraneExplorer: Shipwreck Scholars

Castle Hill on the Crane Estate | Ipswich

Explore a 100 year-old shipwreck on this hike and learn how marine archeologists work to preserve coastal artifacts.

Sunday, December 8

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Saturday, December 14

Saturday, December 14

Full Moon Hike with Adventure East

Peaked Mountain | Monson

Join Adventure East for an exciting evening under the stars as we enjoy a hike lit by the full moon.

Saturday, December 14

Full Moon Hike at World's End

World’s End | Hingham

Experience World's End under the light of the moon!

Saturday, December 14

Saturday, December 14

CraneExplorer: Family Full Moon Hike in the Dunes

Castle Hill on the Crane Estate | Ipswich

See the dunes of the Crane Wildlife Refuge cast in a whole new light and listen for nighttime sounds as you hike under the full moon.

Saturday, December 14

CraneOutdoors: Dunes by the Light of the Full Moon

Castle Hill on the Crane Estate | Ipswich

Enjoy a sunset on Crane Beach and see the dunes on Castle Neck cast in a whole new light as you hike under the full moon.

Saturday, December 14

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Saturday, December 14

Saturday, December 14

Night Tree Celebration at Appleton Farms

Appleton Farms | Hamilton & Ipswich

Help us celebrate the holidays with our wild forest friends!

Saturday, December 14

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Saturday, December 14

CraneExplorer: Coastal Holiday Crafts

Castle Hill on the Crane Estate | Ipswich

Join this interactive education program to learn about treasures found on the beach and make your own coastal holiday crafts!

Saturday, December 14

Saturday, December 14

Bird Walks at World's End

World’s End | Hingham

Grab your binoculars and seek out a wide variety of spectacular birds.

Sunday, December 15

Full Moon Hike at World's End

World’s End | Hingham

Experience World's End under the light of the moon!

Sunday, December 15

CraneExplorer: Family Full Moon Hike in the Dunes

Castle Hill on the Crane Estate | Ipswich

See the dunes of the Crane Wildlife Refuge cast in a whole new light and listen for nighttime sounds as you hike under the full moon.

Sunday, December 15

CraneOutdoors: Dunes by the Light of the Full Moon

Castle Hill on the Crane Estate | Ipswich

Enjoy a sunset on Crane Beach and see the dunes on Castle Neck cast in a whole new light as you hike under the full moon.

Sunday, December 15

Sunday, December 15

deCordova by Moonlight – Full Cold Moon Sculpture Tour

deCordova Sculpture Park and Museum | Lincoln

Enjoy a Moonlight Tour of deCordova Sculpture Park!

Sunday, December 15

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Sunday, December 15

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Sunday, December 15

Sunday, December 15

CraneOutdoors: King Tide Hike

Castle Hill on the Crane Estate | Ipswich

Join this educational hike to view the king tide and learn about The Trustees’ coastal resilience efforts to project our species places.

Saturday, December 21

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Saturday, December 21

Saturday, December 21

CraneOutdoors: Winter Solstice Hike and Fire Pit Adventure

Castle Hill on the Crane Estate | Ipswich

Come Join us for the Winter Solstice and explore Castle Hill and Cedar Point followed by the warmth of a firepit.

Saturday, December 21

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Saturday, December 21

Saturday, December 21

Winter Solstice Walk at Chestnut Hill Farm

Chestnut Hill Farm | Southborough

Celebrate the solstice at Chestnut Hill Farm!

Sunday, December 22

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Sunday, December 22

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Sunday, December 22

Bird Watching Exploration on the Belle Isle Marsh

Belle Isle Marsh | Boston

Bird Watching Exploration on the Belle Isle Marsh

Thursday, December 26

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Thursday, December 26

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Friday, December 27

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Friday, December 27

Friday, December 27

Sensory-Friendly Walk and Learn: Nature's Winter Designs

Powisset Farm | Dover

Discover winter's wonder at Powisset Farm

Friday, December 27

CraneExplorer: Shipwreck Scholars

Castle Hill on the Crane Estate | Ipswich

Explore a 100 year-old shipwreck on this hike and learn how marine archeologists work to preserve coastal artifacts.

Friday, December 27

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Saturday, December 28

CraneOutdoors: Sunset Hike to Cedar Point

Castle Hill on the Crane Estate | Ipswich

Join us as we explore this hidden gem of the Crane Estate at sunset!

Saturday, December 28

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Saturday, December 28

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Sunday, December 29

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Sunday, December 29

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Monday, December 30

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Monday, December 30

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Tuesday, December 31

CraneExplorer: Family Snowy Owl Prowl

Castle Hill on the Crane Estate | Ipswich

Join this guided family hike through the Castle Neck dunes to learn about and search for Snowy Owls - winter visitors from the north!

Tuesday, December 31

CraneOutdoors: Snowy Owl Prowl

Crane Beach on the Crane Estate | Ipswich

Searching for snowy owls in their coastal winter habitat is surely an outing to remember!

Thursday, January 2

Thursday, January 2

Family Walk and Learn: Nature's Winter Designs

Powisset Farm | Dover

Create art inspired by the winter wonderland of Powisset Farm.

Friday, January 3

Friday, January 3

Sensory-Friendly Winter Scavenger Hunt

Rocky Woods | Medfield

Find the hidden winter treasures at Rocky Woods in this sensory-friendly scavenger hunt!

Saturday, January 25

CraneExplorer: Shipwreck Scholars

Castle Hill on the Crane Estate | Ipswich

Explore a 100 year-old shipwreck on this hike and learn how marine archeologists work to preserve coastal artifacts.

Saturday, February 8

CraneExplorer: Shipwreck Scholars

Castle Hill on the Crane Estate | Ipswich

Explore a 100 year-old shipwreck on this hike and learn how marine archeologists work to preserve coastal artifacts.

Saturday, February 8

Saturday, February 8

Owl Prowl at Rocky Woods

Rocky Woods | Medfield

Embark on a winter journey to call forth the owls!

Sunday, February 23

Bird Watching Exploration on the Belle Isle Marsh

Belle Isle Marsh | Boston

Bird Watching Exploration on the Belle Isle Marsh

Saturday, March 8

CraneExplorer: Shipwreck Scholars

Castle Hill on the Crane Estate | Ipswich

Explore a 100 year-old shipwreck on this hike and learn how marine archeologists work to preserve coastal artifacts.

Sunday, March 23

Bird Watching Exploration on the Belle Isle Marsh

Belle Isle Marsh | Boston

Bird Watching Exploration on the Belle Isle Marsh

Sunday, March 30

CraneOutdoors: King Tide Hike

Castle Hill on the Crane Estate | Ipswich

Join this educational hike to view the king tide and learn about The Trustees’ coastal resilience efforts to project our species places.

2024 Trustees Downloadable Map

Download this Trustees property map and checklist to keep track of all of our places you have visited.

A large group of kids walking in a line across a field toward the woods during the day

Guided Hikes For Kids

Looking for ideas to get your kids excited about hiking? We have all kinds of guided hikes across the state geared specifically for families.

Ideas for Hiking the Trustees

Curated lists and ideas for hiking Trustees properties across Massachusetts.

Hike Trustees

The Trustees Hiking Challenge: With over 100 places and hundreds of miles of trails to explore, join our free challenge to get you hiking and exploring M...

Outdoor Adventures

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

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.