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

Beverly Library Spring Book Sale

Beverly Library in Massachusetts hosts hosts their annual book sale and fundraiser. Image is AI generated.
Our annual Friends' Spring Book Sale takes place daily at the main library from Saturday, Saturday May 4 through May 11. The sale will be open daily during regular library hours: Mon.-Thurs., 9AM-9PM; Fri.
9:00 am to 5:00 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

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

Tuesday, May 7

Beverly Library Spring Book Sale

Beverly Library in Massachusetts hosts hosts their annual book sale and fundraiser. Image is AI generated.
Our annual Friends' Spring Book Sale takes place daily at the main library from Saturday, Saturday May 4 through May 11. The sale will be open daily during regular library hours: Mon.-Thurs., 9AM-9PM; Fri.
9:00 am to 5:00 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

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

Music Together - Tuesday in Marblehead

Marblehead, Beverly Farms, Hamilton, Salem, Peabody Music Together
Music Together® is a research-based music & movement program for infants, toddlers, preschoolers, and the grown-ups who love them. Music Together® of Salem classes make it easy for parents/primary caregivers to play a crucial role in activating their child's music development. Classes are 45...
10:00 am to 10:45 am

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

Tabletop Club at Newburyport Library

Kids are invited to come to Newburyport Public Library to play board games.
Are you a fan of... Board games? Dungeons and Dragons? Magic the Gathering? Then the Tabletop Club is for you! Once a month we set up a space for you to get your game on!
3:30 pm to 4:45 pm

Wednesday, May 8

Beverly Library Spring Book Sale

Beverly Library in Massachusetts hosts hosts their annual book sale and fundraiser. Image is AI generated.
Our annual Friends' Spring Book Sale takes place daily at the main library from Saturday, Saturday May 4 through May 11. The sale will be open daily during regular library hours: Mon.-Thurs., 9AM-9PM; Fri.
9:00 am to 5:00 pm

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

Music Together - Wednesday

Marblehead, Beverly Farms, Hamilton, Salem, Peabody Music Together
Music Together® is a research-based music & movement program for infants, toddlers, preschoolers, and the grown-ups who love them. Music Together® classes make it easy for parents/primary caregivers to play a crucial role in activating their child's music development. Classes are 45 minutes...
9:30 am to 11:15 am