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.

Friday, April 26

Friday, April 26

CraneOutdoors: Arbor Day Sunset Hike

Castle Hill on the Crane Estate | Ipswich

Join this Castle Hill hike to enjoy a beautiful sunset and celebrate Arbor Day by learning about trees!

Saturday, April 27

Saturday, April 27

CraneOutdoors: The Castle Hill Hike

Crane Beach on the Crane Estate | Ipswich

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

Saturday, April 27

Saturday, April 27

CraneOutdoors: Sunset Hike to Cedar Point

Crane Beach on the Crane Estate | Ipswich

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

Saturday, April 27

Saturday, April 27

Geology Walk at World's End

World’s End | Hingham

This event has sold out.

Sunday, April 28

Sunday, April 28

Family Walk and Learn: Visiting Vernal Pools

Powisset Farm | Dover

Experience the magic of seasonal vernal pools at Powisset Farm!

Sunday, April 28

Sunday, April 28

Bird Watching Exploration on the Belle Isle Marsh

Belle Isle Reservation | Boston

Join us for a monthly bird walk at Belle Isle Marsh, Boston's last remaining salt marsh.

Sunday, April 28

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

Sunday, April 28

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, May 4

Saturday, May 4

Finding Fungi Guided Mushroom Hike at Chestnut Hill Farm

Chestnut Hill Farm | Southborough

Hunt for wild mushrooms on the farm!

Saturday, May 4

CraneOutdoors: Sunset Hike to Cedar Point

Crane Beach on the Crane Estate | Ipswich

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

Sunday, May 5

Sunday, May 5

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, May 5

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.

Sunday, May 5

Sunday, May 5

Guided Wildflower Walk at Field Farm

The Guest House at Field Farm | Williamstown

Guided wildflower walk led by local naturalists, Pamela Weatherbee and Leslie Reed-Evans.

Saturday, May 11

Saturday, May 11

Family Walk and Learn: Spring Has Sprung!

Powisset Farm | Dover

Explore the wonders of spring at Powisset Farm!

Saturday, May 11

Saturday, May 11

CraneExplorer: Mother's Day Coastal 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 crafts!

Saturday, May 11

CraneOutdoors: The Castle Hill Hike

Crane Beach on the Crane Estate | Ipswich

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

Saturday, May 11

CraneOutdoors: Sunset Hike to Cedar Point

Crane Beach on the Crane Estate | Ipswich

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

Saturday, May 11

Saturday, May 11

Bird Walks at World's End

World’s End | Hingham

Grab your binoculars and join Sally Avery's Bird Walk at World's End.

Sunday, May 12

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, May 18

CraneOutdoors: The Castle Hill Hike

Crane Beach on the Crane Estate | Ipswich

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

Saturday, May 18

CraneOutdoors: Sunset Hike to Cedar Point

Crane Beach on the Crane Estate | Ipswich

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

Saturday, May 18

Saturday, May 18

CraneExplorer: Animals in the Estuary

Crane Wildlife Refuge on the Crane Estate | Essex

Join this interactive education program to take in views of the Crane Wildlife Refuge while exploring and observing estuary critters.

Sunday, May 19

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.

Sunday, May 19

Sunday, May 19

Tranquility in Nature: A CraneWellness Retreat

Castle Hill on the Crane Estate | Ipswich

Join us for a half-day wellness retreat to reconnect with yourself through the healing power of nature.

Sunday, May 19

Sunday, May 19

Artist Walk with Jean Shin at Appleton Farms

Appleton Farms | Hamilton & Ipswich

Engage with art and artist in this talk & hike at Appleton Farms

Tuesday, May 21

Tuesday, May 21

CraneExplorer: Family Full Moon Hike in the Dunes

Crane Beach on the Crane Estate | Ipswich

Enjoy a guided moonlight hike in the Castle Neck dunes with the whole family!

Tuesday, May 21

Tuesday, May 21

CraneOutdoors: Dunes by the Light of the Full Moon

Crane Beach on the Crane Estate | Ipswich

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

Wednesday, May 22

CraneExplorer: Family Full Moon Hike in the Dunes

Crane Beach on the Crane Estate | Ipswich

Enjoy a guided moonlight hike in the Castle Neck dunes with the whole family!

Wednesday, May 22

CraneOutdoors: Dunes by the Light of the Full Moon

Crane Beach on the Crane Estate | Ipswich

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

Wednesday, May 22

Wednesday, May 22

Full Moon Hike at World's End

World’s End | Hingham

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

Thursday, May 23

Thursday, May 23

Full Moon Tours at deCordova

deCordova Sculpture Park and Museum | Lincoln

Explore the Sculpture Park in a Whole New Light!

Thursday, May 23

Full Moon Hike at World's End

World’s End | Hingham

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

Friday, May 24

Full Flower Moon Hike at Powisset Farm

Powisset Farm | Dover

Experience Powisset Farm under the light of the full moon!

Friday, May 24

Full Moon Hike & Meditation at Ward Reservation

Charles W. Ward Reservation | Andover

Join Within Wildlight for a mindful hike up Holt Hill and center yourself with a guided meditation

Friday, May 24

Friday, May 24

A Family-Friendly Night Hike

Fruitlands Museum | Harvard

Join us on the trails at Fruitlands Museum to see WHO-WHO-WHO we may see or hear.

Friday, May 24

Friday, May 24

CraneOutdoors: Sunset Kayak in the Crane Wildlife Refuge

Crane Beach on the Crane Estate | Ipswich

End your day with a sunset kayak trip in the heart of the Crane Wildlife Refuge!

Saturday, May 25

Sensory-Friendly Full Flower Moon Hike at Powisset Farm

Powisset Farm | Dover

Join us for a sensory-friendly Full Moon hike at Powisset Farm.

Saturday, May 25

CraneOutdoors: The Castle Hill Hike

Crane Beach on the Crane Estate | Ipswich

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

Saturday, May 25

CraneOutdoors: Sunset Hike to Cedar Point

Crane Beach on the Crane Estate | Ipswich

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

Saturday, May 25

CraneOutdoors: Sunset Kayak in the Crane Wildlife Refuge

Crane Beach on the Crane Estate | Ipswich

End your day with a sunset kayak trip in the heart of the Crane Wildlife Refuge!

Saturday, May 25

Saturday, May 25

CraneOutdoors: Choate Island Kayak and Hiking Adventure

Crane Beach on the Crane Estate | Ipswich

Kayak and hike your way to the perfect summer day!

Sunday, May 26

Bird Watching Exploration on the Belle Isle Marsh

Belle Isle Reservation | Boston

Join us for a monthly bird walk at Belle Isle Marsh, Boston's last remaining salt marsh.

Sunday, May 26

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.

Sunday, May 26

CraneOutdoors: Sunset Kayak in the Crane Wildlife Refuge

Crane Beach on the Crane Estate | Ipswich

End your day with a sunset kayak trip in the heart of the Crane Wildlife Refuge!

Sunday, May 26

Sunday, May 26

CraneOutdoors: Kayak Historic Fox Creek

Crane Beach on the Crane Estate | Ipswich

Wind through the beautiful channels of Fox Creek and explore the oldest manmade tidewater canal in the United States.

Monday, May 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.

Monday, May 27

CraneOutdoors: Sunset Kayak in the Crane Wildlife Refuge

Crane Beach on the Crane Estate | Ipswich

End your day with a sunset kayak trip in the heart of the Crane Wildlife Refuge!

Monday, May 27

CraneOutdoors: Choate Island Kayak and Hiking Adventure

Crane Beach on the Crane Estate | Ipswich

Kayak and hike your way to the perfect summer day!

Friday, May 31

CraneOutdoors: Sunset Kayak in the Crane Wildlife Refuge

Crane Beach on the Crane Estate | Ipswich

End your day with a sunset kayak trip in the heart of the Crane Wildlife Refuge!

Saturday, June 1

Saturday, June 1

Fire and Food: Matchless Campfire Building & Cooking

Rocky Woods | Medfield

Learn the magic of matchless campfire building at Rocky Woods!

Saturday, June 1

Saturday, June 1

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, June 1

Bird Walks at World's End

World’s End | Hingham

Grab your binoculars and join Sally Avery's Bird Walk at World's End.

Sunday, June 2

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, June 8

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, June 8

Saturday, June 8

Sensory-Friendly Beginner Bird Walk

Powisset Farm | Dover

Join us for a sensory-friendly beginner bird walk at Powisset Farm!

Saturday, June 8

Saturday, June 8

Family Walk and Learn: Meet the Pollinators

Chestnut Hill Farm | Southborough

Get to know the pollinators of Chestnut Hill Farm!

Sunday, June 9

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, June 15

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, June 16

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Thursday, June 20

Full Moon Hike at World's End

World’s End | Hingham

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

Friday, June 21

Full Moon Hike & Meditation at Ward Reservation

Charles W. Ward Reservation | Andover

Join Within Wildlight for a mindful hike up Holt Hill and center yourself with a guided meditation

Friday, June 21

Full Moon Hike at World's End

World’s End | Hingham

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

Saturday, June 22

Full Strawberry Moon Hike at Powisset Farm

Powisset Farm | Dover

Experience Powisset Farm under the light of the full moon!

Saturday, June 22

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, June 22

Family Walk and Learn: Beginner Bird Walk

Powisset Farm | Dover

Join us for a beginner bird walk at Powisset Farm!

Sunday, June 23

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, June 29

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, June 30

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, July 6

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, July 7

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, July 13

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, July 14

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, July 20

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, July 21

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, July 27

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, July 28

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, August 3

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, August 4

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, August 10

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, August 11

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, August 17

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, August 18

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, August 24

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Sunday, August 25

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

Saturday, August 31

Hike with Goats at Powisset Farm

Powisset Farm | Dover

Take a leisurely hike through Powisset with one or more of our friendly goats!

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.

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.