Trails & Sails

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 16-18 & 23-25, 2016!

Enjoy a variety of guided walks, paddles, 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. Events are listed alphabetically by town in five geographic areas of Essex County, Massachusetts (corresponding to this map): NORTH; WEST; CENTRAL; EAST; SOUTH, Essex County.

« 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.

  • Do you need reservations to attend a Trails & Sails event? Probably not! Most events are available on a first-come, first-served basis. In rare cases events will be marked with the “Reservations Required” icon and will list “reservation information” instructions. 

« Check the Trails & Sails Event Updates list to quickly find the new events, updated events or cancellations! Most events are held rain or shine, but could be cancelled at the discretion of the event host.

« Take the Trails & Sails Challenge: FIND YOUR PARK, FIND YOUR STORY! Join us in celebrating Essex Heritage’s 20th anniversary and the National Park Centennial by going to as many Trails & Sails events as possible to enter to win $150 in gift certificates to Dick’s Sporting Goods! Ready to accept? Sign-in! Log-in or Register online and then be sure to fill out the Participant Registration Form at each unique event you attend over the two TRAILS & SAILS weekends. Each time you sign-in at an event, the more likely you are to win.  Go to one event or many over the two weekends. All events are FREE!

« On-the-go? Use your smartphone to access the enhanced Trails & Sails mobile website and your itinerary.

« Connect! Follow Essex Heritage on Twitter or Instagram, or “like us” on Facebook to see event updates, recommendations, and to share your photos. Use #TrailsAndSails to help us find your posts and to stay connected to other Trails & Sails participants. Add #FindYourPark and/or #FindYourStory to help celebrate Essex Heritage’s 20th and the National Park Service 100th anniversaries!

« And GO! But hey, before you go, be safe and be prepared! Always wear appropriate clothing and footwear to Trails & Sails events. Rubber soles are recommended for all events. Children must always be accompanied by an adult. And, handy items to pack in your bag may include: water, snacks, sunscreen, a map of the area, binoculars, field guides, sketchbooks, and a camera so you can enter the Essex Heritage Photo Contest!

« Please Remember! Events are on a FIRST-COME FIRST-SERVED BASIS. Please allow time to arrive early to make sure you get a spot!

Looking for a Printed Guide to Trails & Sails?

After Labor Day (September 5), 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 5, 2016). 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.)

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 special places in this region. Join us.

Hey, Event Hosts

  • If you're already an event host, log-in here.
  • Never hosted before? Get involved! Email Emily to add your site or organization to the Trails & Sails lineup.