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
Appleton Farms in Ipswich Massachusetts offers farm-based Summer Programs for kids ages 5-15

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's So Sweet Festival

Salem Massachusetts' retailers have some sweet surprises in store during the Salem's So Sweet Weekend Festival
Salem Main Streets and the Salem Chamber of Commerce invite you to come enjoy the annual Salem’s So Sweet Chocolate & Ice Sculpture Festival – a decadent tradition of delectable chocolate, sparkling ice sculptures, and Valentine’s Day shopping! Now in its 24th year, Salem’s So Sweet has become...
Where: Downtown Salem
9:00 am to 10:00 pm
♦ Read More →

Winter Family Field Trip: Raptor Road Trip
Families are invited to Joppa Flats Education Center in Newburyport Massachusetts to learn about eagles and their behaviors. Photo: Bill O'Connor
With radios in hand, we will carpool to Bald Eagle viewing spots along the Merrimack River and walk short distances to spot eagles with our binoculars and birding scopes. We will be watch for fishing, and courtship displays. Stay warm and active with small group activities that feature raptor sound...
Where: Joppa Flats Education Center
10:00 am to 12:00 pm
♦ Read More →

Kidleidoscope at Breakheart Reservation
Kidleidoscope is a program designed for preschoolers at Breakheart Reservation in Saugus Massachusetts
Come join our park interpreter for a story time and nature walk! Complete a small craft and explore the woods! Walks are gently paced and approximately 1 mile, though not accessible for strollers. Appropriate for families with children 3-5 years old. Meet at the Visitor Center.
Where: Breakheart Reservation
10:30 am to 11:30 am
♦ Read More →

Family Owl Prowl
Join a Family Owl Prowl at the Ipswich River Wildlife Sanctuary. Photo: Scott Santino
Experience the excitement of an owl prowl as we take a hike under the light of the moon to look and listen for Barred Owls, Great Horned Owls, and Eastern Screech-Owls. Before we head out on our nocturnal adventure, we will learn fun owl facts in our cozy barn using real owl feathers, skulls, and...
Where: Ipswich River Wildlife Sanctuary
5:30 pm to 7:00 pm
♦ Read More →

Saturday, February 7

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's So Sweet Festival

Salem Massachusetts' retailers have some sweet surprises in store during the Salem's So Sweet Weekend Festival
Salem Main Streets and the Salem Chamber of Commerce invite you to come enjoy the annual Salem’s So Sweet Chocolate & Ice Sculpture Festival – a decadent tradition of delectable chocolate, sparkling ice sculptures, and Valentine’s Day shopping! Now in its 24th year, Salem’s So Sweet has become...
Where: Downtown Salem
9:00 am to 10:00 pm
♦ Read More →

NSNP Saturday Srolls at Choate Farm
Come to Choate Farm in Danvers Massachusetts to learn some basic Winter Survival Skills with your family!
Do you and your family have what it takes to survive out in the wilderness?
Where: Choate Farm Conservation Area
10:00 am to 11:30 am
♦ Read More →

CraneExplorer: Valentine's Coastal Craft
Make Valentines crafts from materials that we find along the shore at the Trustees of Reservations Crane Estate in Ipswich, Massachusetts
The Trustees of Reservations invites ages 12 and up to a valentine craft making workshop! This Valentine’s Day, give a gift from the sea! From seaweed pressings to shell collages, beach treasures make beautiful greetings and keepsakes. Join this workshop to learn fun craft ideas and make marine art...
Where: Castle Hill on the Crane Estate
10:00 am to 12:30 pm
♦ Read More →

CraneOutdoors: The Castle Hill Hike
CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
Where: Castle Hill on the Crane Estate
10:00 am to 12:00 pm
♦ Read More →

Music and Movement at North Shore Children's Museum
North Shore, North Shore Childrens Museum in Peabody MA
Music and Movement with Marybeth Maes is an engaging music and movement class for young children at the North Shore Children's Museum. Marybeth brings her guitar and instruments for the children to use while they sing, dance, and play.
Where: North Shore Children's Museum
10:00 am to 11:00 am
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Children's Maple in the Barnyard at Appleton Farms
Visit Appleton Farms' sugaring operation and learn about making maple sugar syrup!
Maple Season is here! This special program for ages 3-11 & their families will focus on the magic of maple from start to finish. We will discover this tradition by observing trees, tasting sap, learning the tools involved, and finally, tasting the sweet product. We will make sure to have time...
Where: Appleton Farms
10:45 am to 3:00 pm
♦ Read More →

Bald Eagles in the Wild for Teens
Teens are invited to Joppa Flats Education Center in Newburyport Massachusetts to learn about eagles and their behaviors. Photo: Bill O'Connor
Head to the most popular spots to search for Bald Eagles. Learn how to spot an eagle in flight, observe their behaviors, and learn how to identify Bald Eagles at different stages of life. Use binoculars, field scopes, and bird guides. Stay active and warm with group challenges about wingspan and...
Where: Joppa Flats Education Center
2:00 pm to 4:00 pm
♦ Read More →

Sunday, February 8

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's So Sweet Festival

Salem Massachusetts' retailers have some sweet surprises in store during the Salem's So Sweet Weekend Festival
Salem Main Streets and the Salem Chamber of Commerce invite you to come enjoy the annual Salem’s So Sweet Chocolate & Ice Sculpture Festival – a decadent tradition of delectable chocolate, sparkling ice sculptures, and Valentine’s Day shopping! Now in its 24th year, Salem’s So Sweet has become...
Where: Downtown Salem
9:00 am to 10:00 pm
♦ Read More →
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