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
Landmark Summer Program at Landmark School in Beverly Massachusetts

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
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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
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Saturday, March 14

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 →

Maple Sugaring at Breakheart Reservation
Come to Breakheart Reservation Saugus Massachusetts to learn about maple sugaring - the process of making syrup..
Come to Breakheart Reservation for this FUN annual event! Experience the process of maple sugarin’ from tapping a tree to sampling real maple syrup.
Where: Breakheart Reservation
10:00 am to 2:00 pm
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Discover Saturdays at Cape Ann Museum
Discover Saturdays for Families at Cape Ann Museum in Gloucester Massachusetts
Enjoy a FREE guided activity (ages 4+) in the gallery. Learn about Cape Ann’s Granite Industry, try a fun art making activity, and join in gallery tour designed for kids and their caregivers, led by a CAM Educator. Afterwards grab a scavenger hunt to explore the property and enjoy the lawn.
Where: Cape Ann Museum Green
10:00 am to 12:00 pm
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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
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2nd Saturday at Lynn Museum
Lynn Museum in Massachusetts offers free admission on the second Saturday of each month.
Come to the Lynn Museum and Historical Society for FREE family fun. Join us on the second and fourth Saturday of each month for FREE admission to the Museum from 10 a.m. – 2 p.m.! You can view our latest exhibitions, purchase Lynn-themed goods in our shop, check out books in our free library, and...
Where: Lynn Museum and Historical Society
10:00 am to 2:00 pm
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Maple Sugaring Saturday at IRWS
Sugaring Off tours are a fun and tasty way to learn about maple sugaring at IRWS
Experience the age-old tradition of maple sugaring at Ipswich River Wildlife Sanctuary! The warm days of late winter awaken the flow of sap in the maples resulting in sweet-smelling, billowing clouds of steam rising from the sugarhouse. On a naturalist-guided walk, learn how to identify a sugar...
Where: Ipswich River Wildlife Sanctuary
10:30 am to 3:30 pm
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Sunday, March 15

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 →

Wonderful Winter Birding
Beginning winter birding is held on the 3rd Sunday of each Winter month at Halibut Point State Park in Rockport Massachusetts
Halibut Point State Park, along the Atlantic migratory path, is an excellent locale for winter birding species you rarely see anywhere else.Winter brings birds and ducks from frozen ponds up north to our seashore. See Harlequin ducks and loons among the winter visitors at this rocky coastal water’s...
Where: Halibut Point State Park
8:00 am to 10:00 am
♦ Read More →
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