Trails & Sails

Explore the North Shore with over 150 Free Events in Essex National Heritage Area's Trails & Sails celebration in Massachusetts.

Essex National Heritage Area sites will offer over 150 free family fun events from September 14-29, 2024 for the annual celebration of TRAILS & SAILS. Discover special places in your backyard and be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds. Find what makes Essex County like nowhere else during Trails & Sails! It’s all FREE and it’s all located within the 34 cities and towns of Essex County.

Enjoy a variety of guided walks, sails, historical tours and other adventures for all ages, skill levels and interests, that will connect you to the spectacular places, history and heritage that define the Essex National Heritage Area—the 34 cities and towns of Boston’s legendary North Shore. It’s all free and it’s all located within the 34 cities and towns of Essex County including the communities of Beverly, Salem, Gloucester, Newburyport, Lawrence, Saugus and more.

Most events will accommodate between 12 and 50 participants on a first-come, first-served basis, with the exception of a few reservation-required events. Here is the lineup of all 2025 events

Watch our site for our favorite upcoming Trails & Sails 2025 events!

When: 
Daily, September 13-28, 2025
Prices: 
Free
Phone: 
978.740.0444
Smileland Pediatric Dental Care Waltham Malden Massachusetts

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Saturday, January 31

CraneOutdoors: The Castle Hill Hike

CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
10:00 am to 12:00 pm

Animal Tracks | Family Nature Series

Essex County Greenbelt teams up with North Shore Nature Programs for a wildlife hike in Ipswich Massachusetts!
​​​​​​​​​​​​​​This event with North Shore Nature Programs is geared toward families of all ages who would like to learn about the signs and tracks that animals leave behind!  We will explore outdoors and look at tracks, chewed sticks, scat, nests, beaver constructions and more! Waterproof and warm...
10:00 am to 11:30 am

CraneExplorer: Family Full Moon Hike in the Dunes

Walk through the Crane Wildlife Refuge in Ipswich Massachusetts with the Trustees under the full moon.
There is almost nothing more peaceful than a evening walk at the Crane Estate, and we would like to invite your family to join us for a unique hiking experience. With the full moon rising over the Atlantic, we’ll start with a sunset stroll along Crane Beach admiring this spectacle before heading...
4:30 pm to 6:30 pm

Sunday, February 1

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Watching the Coastal Edge at Halibut Point

Tour the WWII era observation tower at Halibut Point State Park in Rockport Massachusetts.
Meet at the Halibut Point State Park visitors center to learn about the role Halibut Point has played in America’s military history. One day after the 1941 Pearl Harbor attack, U.S.
11:00 am to 12:30 pm

CraneOutdoors: Family Winter Wildlife Walk

Come explore the dunes on Castle Neck and Crane Beach in Ipswich Massachusetts to learn about winter wildlife.
A CraneOutdoors Family Winter Wildlife Walk will take you on a stroll through the Crane Beach dunes while learning about the plants and animals that call this special place home. You may be familiar with Crane Beach, but have you ever visited the dune trails? The dunes of Castle Neck are a much...
1:00 pm to 3:30 pm

Sunday STEAM Club at North Shore Children's Museum

Visit Peabody MA, NorthShore, North Shore Children's Museum
Join in on Sundays at 2:30 for STEAM Club for ages 5-11. Each week participants will explore science, technology, engineering, art, and math with our NSCM staff! Every STEAM club session will see your kids participating in hands-on activities while exploring a new topic. Space is limited, please...
2:30 pm to 4:00 pm

Snow Moon Winter Celebration

Come to Spencer-Pierce-Little Farm to celebrate February's Snow Moon in Newbury Massachusetts!
Come to Spencer Peirce Little Farm to celebrate the season under the stillness of February's full Snow Moon! Spencer-Peirce-Little Farm opens its gates for a winter celebration that honors the beauty of the land, th
3:00 pm to 6:00 pm

CraneExplorer: Family Full Moon Hike in the Dunes

Walk through the Crane Wildlife Refuge in Ipswich Massachusetts with the Trustees under the full moon.
There is almost nothing more peaceful than a evening walk at the Crane Estate, and we would like to invite your family to join us for a unique hiking experience. With the full moon rising over the Atlantic, we’ll start with a sunset stroll along Crane Beach admiring this spectacle before heading...
4:30 pm to 6:30 pm

Monday, February 2

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm