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
Save the Dates
Trails & Sails will return in 2026 taking place September 12-27!
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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.
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.
Featured Events
Our 2026 Sponsors
Become a Sponsor
Sponsoring Trails & Sails keeps the event series free to attend and supports heritage stewards in their effort to attract new audiences.
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?
Transportation Information
There are multiple alternatives to driving that can be utilized when planning your next Trails & Sails adventure!