Sail

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.

When: 
Daily, September 13-28, 2025
Hike
Walk
Exploration
Museum
Festival
Discovery
Sailing
Outdoor Activity
Boat
Sail
Activity
Trails & Sails 2025

Kids Sail Free on the Schooner Lannon

Kids ride free on the 10:30am an Noon Saturday Cruise on the Schooner Lannon through Summer

Schooner Thomas E. Lannon is a fixture on the Gloucester Harbor vista throughout the day in the warm months, but to really experience the Lannon, you need to come aboard and go for a cruise!  Sail and see lighthouses, castles, scenic beaches, and magnificent waterfront homes.

When: 
Saturdays through July and August 2025, 10:30am or Noon
Location: 
Schooner Thomas E. Lannon
Gloucester
History
Boat Ride
Schooner
Boat
Sail
Heritage

Marine Society Outings on the Schooner FAME

Schooner Fame's Marine Society Outings are designed for children ages 8-14 out of Salem Massachusetts

Marine Society Outings are designed for children ages 8-14. Each outing is five hours on the water, 9:00-2:00, usually with a stop at the islands to swim off the boat (swimming is optional). Participants raise and trim the sails, learn knots, steer the boat, and play silly camp games. We accept 16 kids per session. Cost is $85. For Salem residents the cost is just $55, thanks to the Marine Society! In the event of bad weather, Outings may be postponed to the next day, or cancelled, in which case you will receive a refund.

When: 
Wednesday, August 6, 2025 9am-2pm
Location: 
Schooner Fame
Salem
Tour
History
Sailing
Maritime
Schooner
Sail

Schooner Sail on the Thomas E. Lannon

Schooner Lannon is offering a free sail - first come first served - during Trails and Sails 2019

Picture yourself relaxing on the deck of this beautiful 65- foot schooner as she sails out of Gloucester harbor on a light southwesterly breeze. Join us for a sail and get a taste for what it was like to sail on a fishing schooner a hundred years ago. Help the crew raise the sails, or just sit back and take in the sights and sounds of Gloucester’s coastline.

When: 
Saturday, September 28, 2019 11:30-1pm
Location: 
Schooner Thomas E. Lannon
Gloucester
Sail
Schooner
Trails & Sails 2019
Sailing

Kay Ellis Scholarship Fundraiser

The Kay Ellis Scholarship Fundraiser Sail and Dock Party August 20, 2018

Come to the Kay Ellis Memorial Fundraiser for a night of fun in Gloucester! Enjoy a sunset schooner cruise aboard the Lannon or Ardelle, followed by dinner, dessert, local music, and a pirate raffle. In 2017 & 2018, $9,000 was awarded each year to students studying Hospitality and Tourism. Join us to help support the future youth of our Cape Ann industry.

When: 
Monday, August 19, 2019 6-10pm
Location: 
Schooner Thomas E. Lannon
The Gloucester House
Gloucester
Fundraiser
Benefit
Scholarship
Sail
Schooner
Dinner
Charity

Spring Launch of the Schooner Ardelle

Schooner Ardelle will be launched at Maritime Gloucester on April 27 at 12:30!

Maritime Gloucester invites boating enthusiasts of all ages to the Spring launching of the Schooner Ardelle! Harold Burnham and his volunteer crew have been getting his beautiful Pinky Schooner Ardelle ready for another exciting season sailing form Maritime Gloucester and she's ready to launch! The launching will take place at the Maritime Gloucester Marine Railway, the oldest continuously operating marine railway in the United States.

When: 
Saturday, April 27, 2013 12:30pm
Location: 
Maritime Gloucester
Gloucester
History
Marine
Boat
Sail
Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury 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!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

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.
Where: Saugus Iron Works National Historic Site
7:00 am to 7:00 pm
♦ Read More →

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....
Where: Downtown Salem
9:00 am to 5:00 pm
♦ Read More →

CraneExplorer: Coastal Holiday Crafts
Make holiday gifts with beach treasures from the Crane Wildlife Refuge in Ipswich Massachusetts
This holiday season, give a gift from the sea! Beach treasures make beautiful holiday ornaments, jewelry, and keepsakes. Join this workshop to take a beach walk to collect coastal treasures and then make some coastal crafts with our educators. Bring your own shells and beach treasures and we will...
Where: Castle Hill on the Crane Estate
10:00 am to 3:00 pm
♦ Read More →

Deck The Halls: Hammond Castle
A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
Where: Hammond Castle Museum
10:00 am to 8:00 pm
♦ Read More →

Christmas at Castle Hill | A Nod to Nature
Christmas at Castle Hill | A Nod to Nature is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
Where: Castle Hill on the Crane Estate
10:00 am to 8:00 pm
♦ Read More →

Santa's Workshop
Santa's Workshop in Newburyport, Massachusetts. Visit Newburyport MA during the holidays
Newburyport is a favorite local town to shop - especially during the holidays. Bring the family to Newburyport to visit Santa in his traditional workshop, share your wish list, and snap a photo with Mr. Claus!
Where: Santa's Workshop
11:00 am to 2:00 pm
♦ Read More →

Take a Trolley Ride with Scrooge!

Salem Trolley Christmas Carol, Fun Holiday Events north of Boston, Trolley Ride with Scrooge
Join Scrooge on the Salem Trolley as you ride through Salem Massachusetts in this rolling production performed by the Griffen Theater . Now entering into it's 39th Season, this humorous & whimsical interactive performance reanimates Dickens’ timeless seasonal holiday classic. Experience...
Where: Salem Trolley
2:00 pm to 9:30 pm
♦ Read More →

Low-Sensory Play at North Shore Children's Museum
Low-Sensory Play at NorthShore Children's Museum in Peabody Massachusetts
Join us for a low-sensory play session. For some children, visiting places like NSCM can be over-stimulating. This special play session will have reduced noise, crowds, and stimulation. While medical diagnosis is not required, we encourage that these limited tickets be used for families with a...
Where: North Shore Children's Museum
2:00 pm to 4:00 pm
♦ Read More →

The Nutcracker Panto - Matinee
Come enjoy a Nutcracker Panto performed by Theater in the Open at the Firehouse Center for the Arts!
The tree is lit up and the stockings are hung and Clara’s Christmas is perfect…except for her Uncle Drosselmeyer sitting up on that clock and the sudden rat infestation…sounds like panto time!Edward Speck and Joshua Shack return to direct another cracking holiday panto, this time seizing on...
Where: Firehouse Center for the Arts
3:00 pm
♦ Read More →

The Nutcracker Panto
Come enjoy a Nutcracker Panto performed by Theater in the Open at the Firehouse Center for the Arts!
Theater in the Open is happy to be back at the Firehouse for our production of A Nutcracker Panto, written by Edward F. Speck and adapted from the classic holiday ballet. Presented in the traditional British panto style, this holiday send-up is a family friendly romp through Clara’s adventure with...
Where: Firehouse Center for the Arts
7:00 pm
♦ Read More →

Sunday, December 21

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.
Where: Saugus Iron Works National Historic Site
7:00 am to 7:00 pm
♦ Read More →

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!
Where: Halibut Point State Park
7:00 am to 6:00 pm
♦ Read More →

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....
Where: Downtown Salem
9:00 am to 5:00 pm
♦ Read More →

Christmas at Castle Hill | A Nod to Nature
Christmas at Castle Hill | A Nod to Nature is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
Where: Castle Hill on the Crane Estate
10:00 am to 8:00 pm
♦ Read More →

Deck The Halls: Hammond Castle
A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
Where: Hammond Castle Museum
10:00 am to 8:00 pm
♦ Read More →

Santa's Workshop
Santa's Workshop in Newburyport, Massachusetts. Visit Newburyport MA during the holidays
Newburyport is a favorite local town to shop - especially during the holidays. Bring the family to Newburyport to visit Santa in his traditional workshop, share your wish list, and snap a photo with Mr. Claus!
Where: Santa's Workshop
11:00 am to 2:00 pm
♦ Read More →

Winter Solstice Hike | Ward Reservation
Come for a solstice hike at Ward Reservation to celebrate the Winter Solstice in North Andover Massachusetts
The Explore! North Shore hiking series will get you outside and moving at some lesser explored Trustees properties across the Northeast Region, at the right time of year to see these special places shine. These beginner hikes will not be too strenuous, and will offer frequent stops for learning and...
Where: Ward Reservation
1:00 pm to 3:30 pm
♦ Read More →

Take a Trolley Ride with Scrooge!

Salem Trolley Christmas Carol, Fun Holiday Events north of Boston, Trolley Ride with Scrooge
Join Scrooge on the Salem Trolley as you ride through Salem Massachusetts in this rolling production performed by the Griffen Theater . Now entering into it's 39th Season, this humorous & whimsical interactive performance reanimates Dickens’ timeless seasonal holiday classic. Experience...
Where: Salem Trolley
2:00 pm to 9:30 pm
♦ Read More →

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...
Where: North Shore Children's Museum
2:30 pm to 4:00 pm
♦ Read More →

The Nutcracker Panto - Matinee
Come enjoy a Nutcracker Panto performed by Theater in the Open at the Firehouse Center for the Arts!
The tree is lit up and the stockings are hung and Clara’s Christmas is perfect…except for her Uncle Drosselmeyer sitting up on that clock and the sudden rat infestation…sounds like panto time!Edward Speck and Joshua Shack return to direct another cracking holiday panto, this time seizing on...
Where: Firehouse Center for the Arts
3:00 pm
♦ Read More →
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