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
Sports Camps, Speciality Camps, Day Camps in Danvers MA

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 →

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 →

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 →

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 →

Saturday, December 13

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 →

Breakfast with Santa
Kids will enjoy breakfast with Santa at the Hamilton Wenham Community House
Come and enjoy a continental style breakfast and get your picture taken with Santa. We will also have a letter writing station and music entertainment.
Where: Community House Of Hamilton & Wenham
8:00 am to 12:30 pm
♦ Read More →

Middle Street Walk 2025
The lighting of the Lobster Trap Tree is part of Middle Street Walk's finale in Gloucester Massachusetts.
The Annual Middle Street Walk is a great way to experience Gloucester's Historic District and waterfront while having Holiday fun with the family.
Where: Downtown Gloucester
9:00 am to 5:00 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 →

Boot Camp For Birth Support & Beyond
Boot Camp For Birth Support & Beyond for caregivers at Beverly Hospital in Massachusetts
Most education surrounding childbirth focuses on the person carrying the child, as it rightly should. Those in the role of supporting childbirth (spouses, significant others, couples using a surrogate, etc) should be equally as prepared for the joys and challenges in store. In this class you’ll...
Where: Beverly Hospital
9:00 am to 11:00 am
♦ Read More →

Newburyport Holiday House Tour 2025
Newburyport Holiday House Tour hosted by the Newburyport PTO Kitchen Tour
Enjoy touring private residences and unique spaces throughout Greater Newburyport, all decorated in holiday style both inside and out. Your self-guide tour will lead you through each of our homes all decked out both inside and out in holiday style reflecting the homeowner’s individual celebrations...
Where: Downtown Newburyport
9:30 am to 4:00 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 →

Middle Street Walk Gingerbread Contest 2025
Middle Street Walk Gingerbread Contest entries can take any shape.
Everybody is invited to enter the Gingerbread Contest for the Middle Street Walk in Gloucester this year! Groups and individuals are encouraged to get creative and come up with entries that can take any shape.  All entries will be judged prior to the start of the Middle Street at 10am. 
Where: Sawyer Free Library
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 →
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