Trails & Sails

Now in its 24th year, Trails & Sails is your ticket to adventure across Essex County, Massachusetts – a region recognized as a National Heritage Area for its rich history, cultural treasures, and natural landscapes. Each September, this vibrant event series provides access to hundreds of unique experiences such as guided hikes and paddles to behind-the-scenes tours, historic reenactments, interactive exhibits, artisan demos, community celebrations, and much more. Whether you’re a history buff, nature lover, or just curious to discover something new to love in your own backyard, Trails & Sails has something for everyone.