Trails & Sails: Two Weekends of Walks and Water

Trails & Sails: Two Weekends Of Walks and Water

Log In or Register to create a customized itinerary of YOUR favorite Trails & Sails events! It’s a great way to help navigate your Trails & Sails weekends and you’ll receive email notifications if there is a change to any event on your itinerary.

Explore Essex County's historic, cultural and natural sites during two weekends of 150+ FREE events during Trails & Sails: Two Weekends of Walks and Water, September 19-21 & September 26-28, 2014!

Enjoy a variety of guided walks, sails, historical tours and other adventures for all ages, skill levels and interests, that will connect you to the spectacular places, history and heritage that define the Essex National Heritage Area—the 34 cities and towns of Boston’s legendary North Shore. It’s all free and it’s all located within the 34 cities and towns of Essex County including the communities of Salem, Gloucester, Newburyport, Lawrence, Saugus and more.

Get Started!

« Search the online event listing for the most up to date event information and to find Trails & Sails events by region, community, type, event title or description.

« Log In or Register for Trails & Sails to create your own customized itinerary by bookmarking your favorite events! You’ll also receive email notifications if there is any change to an event on your itinerary. Please remember, adding an event to your itinerary is NOT A RESERVATION. Most events are available on a first-come, first-served basis.

« Check the Trails & Sails Event Updates list to quickly find the new events, updated events or cancellations!

« Take the Trails & Sails Challenge: Move It! Challenge yourself during Trails & Sails by participating in Essex Heritage and the YMCA of the North Shore’s Move It! 100 Miles in 100 Days Challenge. Ready to accept? Register for Move It! online and start using the Move It! Mileage Tracker to log any miles you run, swim, hike and bike from July – October, and you’ll earn milestone prizes along the way!


Use your mobile device to access the Trails & Sails mobile website, event listing and your itinerary.

Keep In Touch

Make Trails & Sails last all year long -- become an Essex Heritage member! As an Essex Heritage member there are many opportunities to connect to and support the resources in this region. Join us!

Looking for a Printed Guide to Trails & Sails?

After September 1, there are three ways to get your hands on a printed guide: