Trails & Sails: Two Weekends of Walks and Water

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 18-20 & September 25-27, 2015!

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 Move It, Essex Heritage and the YMCA of the North Shore’s campaign to be more active in the Essex National Heritage Area’s great outdoors. 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.


Use your mobile device to access the Trails & Sails mobile website 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 7, there are three ways to get your hands on a printed guide:

  1. Essex Heritage Members will receive a printed guide in the mail in September. Become a member!
  2. A limited number of printed guides will be available for FREE at Essex National Heritage Area Regional Visitor Centers, and Eastern Bank locations Essex County, MA. The guides will be available after Labor Day (after September 7, 2015). Before you go, we recommend that you call ahead to check hours and to confirm that guides are still available.
  3. Send $5 to Essex Heritage and we'll mail a guide directly to you! Cash or check can be mailed to: Essex Heritage, 10 Federal Street, Suite 12, Salem MA 01970. (Fee covers printing and postage.)

Hey, Event Hosts

If you are interested in hosting an event, Email Emily!