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Weather Update: A nor’easter hitting the coast of Massachusetts (September 26 – 27) has affected some Trails & Sails events.
Please check the calendar for an event’s status.

Trails & Sails

Discover the extraordinary in your own backyard

Trails & Sails

Discover the extraordinary in your own backyard

Trails & Sails

Discover the extraordinary in your own backyard

The Countdown is Over!

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Celebrating 25 Years

Celebrating its 25th year in 2026, Trails & Sails is your ticket to discovering extraordinary places in your own backyard. Be guided through unique experiences on land and sea, explore historic properties, and take part in all kinds of cultural activities.

Find what makes Essex County like nowhere else.

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Featured Events

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27

Merrimack Mishoon Canoe, Indigenous Family Programs

at – calendar-day-dark
Newburyport
Due to inclement weather, this event has been moved to the inside of the Custom House Maritime Museum. Imagine Studios and Newburyport Indigenous Peoples Day Event (10/10/2026) welcomes the public to view the Merrimack Mishoon, 20 foot dugout canoe, and learn about Indigenous maritime traditions with cultural artisans and educators, Larry Spotted Crow Mann (Ohketeau…
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Featured Themes for 2026

Each year, we highlight multiple themes of significant importance to the Essex National Heritage Area.

Stories We Share

Events that uncover powerful stories you haven’t heard before, and why they still matter today.

Life by the Water

Events that explore the many ways the ocean, rivers, and harbors have shaped our communities, and why their health matters.

Outdoor Explorations

Events that help people discover the winding trails and natural beauty that surrounds us, and how we can protect the places we love.

Essex County Revolution 250

Events that highlight Essex County’s role in the American Revolution as we commemorate the 250th Anniversary.

Our 2026 Sponsors

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Become a Sponsor

Sponsoring Trails & Sails keeps the event series free to attend and supports heritage stewards in their effort to attract new audiences.

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Host an Event

Do you have a historic site you want to show off? Or a special local industry you want to share with people?

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Transportation Information

There are multiple alternatives to driving that can be utilized when planning your next Trails & Sails adventure!

Getting There

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