Sail

Trails & Sails

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

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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

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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:

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Sail on the Schooner Fame

Take a sailing tour aboard Schooner Fame of Salem for Trails & Sails 2023!

Set sail on a full-scale replica of the famous 1812 privateer schooner FAME. FAME is a replica of a privateer schooner that sailed from Salem during the War of 1812! We sail up to five times a day between May and October from Pickering Wharf in Salem.

When:

Friday, September 15, 2023 3:30-5pm

Location:

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Father's Day Sunset Sail

Enjoy a sunset sail with dad aboard the Schooner Thomas Lannon on Fathers Day!

Join us for a Father's Day Sunset Sail! Sit back with a beverage and enjoy the sunset, or help the crew raise the sails as we head out through Gloucester's scenic working waterfront.

When:

Sunday, June 20, 2021 6:30pm

Location:

Schooner Thomas E. Lannon

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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

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Kay Ellis Scholarship Fundraiser

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

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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:

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Appleton Farms offers great farm-based Vacation Week Programs for kids ages 5-11

Today's Events
Upcoming Events

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

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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Nice n' Easy Hike at Breakheart Reservation

Join the Park Interpreter for this weekly guided hike! Each trip will highlight natural and historic features unique to Breakheart. Hikes are moderately paced and range from 2-3 miles over sometimes uneven and rocky terrain. Best for ages 8 years and up. Meet at the Visitor Center.

Where: Breakheart Reservation

9:30 am to 11:30 am

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CraneOutdoors: The Castle Hill Hike

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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Gloucester's So Salty 2026

Celebrate the fish city’s recognizably salty character with local cultural institutions and businesses during the 5th Annual Gloucester’s So Salty festival sponsored by the Cape Ann Museum in partnership with Discover Gloucester! This annual event brings over 2,000 people to the downtown area each...

Where: Downtown Gloucester, Where: Cape Ann Museum, Where: Gloucester Unitarian Universalist Church , Where: Sawyer Free Library Temporary Space, Where: Local Colors

10:00 am to 4:00 pm

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Native Seed Sowing at Long Hill

Join Cole Campbell, production horticulturist at Native Plant Trust, for this native seed-sowing workshop at Long Hill Public Garden in Beverly, MA. Learn about our native plant seeds, and then get your hands in the soil to sow some seeds that you can take home with you.

Where: Long Hill and Sedgwick Gardens

11:00 am to 12:30 pm

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Sunday, January 25

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

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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Explore! North Shore: Winter Hike at Moraine Farm

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: Moraine Farm

10:00 am to 12:30 pm

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Gloucester's So Salty 2026

Where: Downtown Gloucester, Where: Cape Ann Museum, Where: Gloucester Unitarian Universalist Church , Where: Sawyer Free Library Temporary Space, Where: Local Colors

10:00 am to 4:00 pm

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Raptor Roundup: Meet Live Birds of Prey at IRWS

Get a close look at some live local birds of prey while keeping warm in our barn! Learn each bird's unique story, discover why raptors play such a vital role in our environment, and explore their amazing adaptations, like keen eyesight and powerful talons, that help them survive in the wild....

Where: Ipswich River Wildlife Sanctuary

11:00 am to 12:30 pm

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Watching the Coastal Edge at Halibut Point

Meet at the Halibut Point State Park visitors center to learn about the role Halibut Point has played in America’s military history. One day after the 1941 Pearl Harbor attack, U.S.

Where: Halibut Point State Park

11:00 am to 12:30 pm

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Amesbury Winter Market

Amesbury Market Daze is your friendly local community marketplace. We take pride in curating a marketplace that showcases local art and food from talented local artisans, chefs, farmers, creators and curators of surrounding Amesbury, Massachusetts. Join us throughout the year to curate and foster a...

Where: Barewolf Brewing

12:00 pm to 4:00 pm

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CraneOutdoors: Family Winter Wildlife Walk

A CraneOutdoors Family Winter Wildlife Walk will take you on a stroll through the Crane Beach dunes while learning about the plants and animals that call this special place home. You may be familiar with Crane Beach, but have you ever visited the dune trails? The dunes of Castle Neck are a much...

Where: Crane Wildlife Refuge on the Crane Estate

1:00 pm to 3:30 pm

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Sunday STEAM Club at 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

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