About

Celebrating its 25th year in 2026, 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.

Trails & Sails is organized and coordinated by Essex Heritage, the regional non-profit working to preserve and enhance natural, cultural, and historic resources around Essex County. Essex Heritage works with many non-profit, community, and small business partners who demonstrate the importance of these assets during Trails & Sails by coordinating free events. This can take many shapes; a historical society might offer a lecture, a conservation group could lead a guided hike, an arts consortium might coordinate open studios, or a local sailing vessel might offer harbor tours. Once events are in the works, Essex Heritage becomes the marketing engine to promote Trails & Sails. This is done through the digital and print promotion of the entire series including the publication of a printed guide, an online and mobile-friendly website for event listings, and social media advertising.

Disclaimer:
The views, opinions, and content presented by individual event hosts during Trails & Sails are solely those of the hosts and do not necessarily reflect the views or policies of Essex Heritage or its partners. Essex Heritage is not responsible for the content of any events or materials shared by participating organizations. If you have any questions about an event you attended, please contact us.