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
Adirondack Leadership Program at Gordon College’s La Vida Center

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

Tuesday, May 19

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

Barnyard Story Hour at Appleton Farms

Kids can meet the barnyard animals and hear a story at Appleton Farms in Ipswich Massachusetts.
Bring your little ones to Appleton Farms for our farm-fresh story hour. We will read books about animals and nature, maybe sing a song or two, then head up to the carriage barn to visit our Nubian goats, Angora rabbits and see what other animals are out and about on the farm. We will engage in...
10:30 am to 11:30 am

Wednesday, May 20

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

Stargazing at Mendel Observatory

Mendel Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night
The Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night (weather permitting) starting at dusk or 7:30 pm, whichever is later.  When special astronomical events of interest occur (total lunar eclipses, etc.) the Obs
7:00 pm

Thursday, May 21

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

Friday, May 22

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, May 23

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

Family Day at the Bird Banding Station

Kids will learn about local and migrating birds at Joppa Flats Education Center in Newburyport Massachusetts
There's nothing like a visit to Parker River National Wildlife Refuge for wonderful family nature experiences, and seeing the bird banding station in operation is at the top of the list. See Mass Audubon scientists evaluate, examine, and release migrating songbirds while you learn about migration...
9:00 am to 11:30 am

Turtle Time at IRWS

Kids and families will explore IRWS wetland in search of painted and snapping turtles.
Explore our wetlands in search of these fascinating reptiles. Walk about a half mile to visit areas where turtles like to nest and bask in the sun, look at and touch real turtle shells, and, with a little luck, get an up-close look at a painted turtle. Conclude with a trip to the Rockery to see if...
10:00 am to 2:30 pm

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