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
Shore School in Beverly Massachusetts offers a host of Summer programs for kids aged 5-12

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 →

Boston Bruins Annual Pajama Drive
Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 pm
♦ Read More →

Read to a Dog at APL
Kids are invited to read to a dog at Amesbury Massachusetts Public Library. Image generated with AI.
The Amesbury Public Library invites kids to come read to a dog at the Library! Read to a dog to help improve reading skills and get comfortable with reading aloud with only a very cuddly dog to hear you! This program will have Gus, a certified reading dog, and his caretaker at the library in our...
Where: Amesbury Public Library
3:45 pm to 4:30 pm
♦ Read More →

Dungeons & Dragons at the G.A.R. Library
Dungeons and Dragons at the GAR Memorial Library in West Newbury Massachusetts
Come to this ongoing campaign using The Dragon of IceSpire Peak. Bring your own character, play one of ours,  or we can help you create one. All are welcome.
Where: The G.A.R. Memorial Library
4:30 pm to 5:30 pm
♦ Read More →

Stargazing at Mendel Observatory
Mendel Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night
The Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night (weather permitting) starting at dusk or 7:30 pm, whichever is later.  When special astronomical events of interest occur (total lunar eclipses, etc.) the Obs
Where: Mendel Observatory at Merrimack College
7:00 pm
♦ Read More →

Thursday, February 12

Boston Bruins Annual Pajama Drive
Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 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 →

LEGO Club at Danvers Library
LEGO club at Danvers Library Massachusetts
Peabody Institute Library - Danvers invites kids to an afternoon of building and fun! Activities will include free build, themes and instructional design. All structures will remain on display in the Children’s Room till the following weeks's session
Where: Peabody Institute Library - Danvers
3:30 pm to 4:30 pm
♦ Read More →

Friday, February 13

Boston Bruins Annual Pajama Drive
Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 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 →

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 →

Saturday, February 14

Valentine's Day
12:00 am to 11:59 pm
♦ Read More →

Boston Bruins Annual Pajama Drive
Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 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 →

LEGO World: Wonderealms
Drop in at LEGO World: Wonderrealms at Wenham Museum in Wenham Massachusetts
This all-new experience invites visitors to explore an extraordinary LEGO world where creativity knows no bounds. From enchanted forests and futuristic skylines to pirate coves and steam-powered frontiers, each realm is packed with intricate details, playful surprises, and clever touches you won’t...
Where: Wenham Museum
9:00 am to 4:00 pm
♦ Read More →
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