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 15-24, 2023 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 2023 events

Watch our site for our favorite upcoming Trails & Sails 2023 events!

When: 
Daily, September 15-24, 2023
Prices: 
Free
Phone: 
978.740.0444
A Landmark Summer Experience at Landmark School in Beverly Massachusetts prepare students for success in the fall and beyond.

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 3:59 pm

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

Home & Food Truck Show | Topsfield

Home and Food Truck show at the Topfield Fairground in Massachusetts
April 20th & 21st. FREE admission and FREE parking. All INDOORS & Enjoy the Food Trucks outside. Speak to leading home industry professionals to plan your spring home projects.
10:00 am to 6:59 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...
7:00 pm to 9:00 pm

Tuesday, April 23

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 3:59 pm

Home & Food Truck Show | Topsfield

Home and Food Truck show at the Topfield Fairground in Massachusetts
April 20th & 21st. FREE admission and FREE parking. All INDOORS & Enjoy the Food Trucks outside. Speak to leading home industry professionals to plan your spring home projects.
10:00 am to 6:59 pm

Barnyard Story Hour at Appleton Farms

Kids can meet the barnyard animals and hear a story at Appleton Farms in Ipswich Massachusetts.
Barnyard stories really come alive when you get to see the main characters in real life! Bring the kids down to Appleton Farms for our farm-fresh version of story time. Explore the farmstead, visit our learning garden, see our cows and rabbits, and find a spot to play under a shady tree in our...
10:30 am to 11:30 am

STEM Structures at NPL

Kids are invited to come to NPL to make STEM structures during winter break! Newburyport Massachusetts
Come play with a variety of building toys, including magnetic tiles and straws and connectors. Kids of all ages and abilities are welcome, but please take note that some of these building toys have small pieces. Drop in any time between 3:00 and 4:30 p.m. to participate.
3:00 pm to 4:30 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...
7:00 pm to 9:00 pm

Wednesday, April 24

Fiddleheads | Preschool Drop-Off Series

The Fiddlehead program at Appleton Farms encourages kids 3-5 to explore their environment in Ipswich Massachusetts
Spring has sprung! It is an excellent time of year for exploring and learning on the farm. We will be planting and harvesting in our garden, taking care of our animals and finding all the signs of spring that nature divulges. Join us on Wednesday mornings from 9:30AM to 12:30PM for a preschool drop...
9:30 am to 12:30 pm

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 3:59 pm

We Walk the Woods!

Walk the trails in a group at Harold Parker State Forest Every Wednesday at 10am
Walk the trails with a group at Harold Parker State Forest every Wednesday at 10:00 a.m. – Meeting location varies weekly. Email trek.reef@mass.gov for location.
10:00 am to 12:00 pm

Home & Food Truck Show | Topsfield

Home and Food Truck show at the Topfield Fairground in Massachusetts
April 20th & 21st. FREE admission and FREE parking. All INDOORS & Enjoy the Food Trucks outside. Speak to leading home industry professionals to plan your spring home projects.
10:00 am to 6:59 pm

Spring Blooms at the Stevens-Coolidge Estate

Spring Blooms at the Trustees Stevens Coolidge Estate in North Andover!
Join The Trustees of Reservations at our new entrance location showcasing contemporary gardens, historical gardens, and our Garden Gateway visitor orientation center at 153 Chickering Road, North Andover MA.
10:00 am to 5:00 pm