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
Summerquest Camp for kids aed 5-14 at the Crane Estate in Ipswich Massachusetts

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

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

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 am to 6:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
9:00 am to 5:00 pm

Mini Movers at North Shore Children's Museum

Things to do for children in Peabody MA
Mini Movers is an engaging dance and movement class for young children at the North Shore Children's Museum. Led by experienced instructors, the program introduces young children to the world of dance in a safe and nurturing environment.
10:00 am to 11:00 am

Sing & Dance with the Music Man

Sing & Dance with the Music Man Brian Doser in Hamilton visit Massachusetts
Come join the fun at Community House Of Hamilton & Wenham Monday, Thursday and Saturday mornings at 10am for 30 - 45 minutes of great music with Brian Doser! Sing and dance with the Music Man during a family concert, featuring familiar and original tunes, performed by local dad and musician,...
10:00 am to 10:45 am

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, November 6

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

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

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 am to 6:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
9:00 am to 5:00 pm

Friday, November 7

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

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

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 am to 6:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
9:00 am to 5:00 pm

Saturday, November 8

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

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