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Presented by Essex Heritage, Trails & Sails features more than 150 free events over 10 days, from Friday, September 20 through Sunday, September 29. Events celebrate the elaborate variety of historic, cultural, and natural resources in the Essex National Heritage Area: the 34 cities and towns of Essex County. 

Trails & Sails was created by Essex Heritage 18 years ago to highlight the unique character of the Area by connecting people to its special places. Essex Heritage is a non-profit organization that takes a community-driven approach to heritage conservation and economic development. Working through public-private partnerships, Essex Heritage uses the Area’s heritage resources in new ways to engage diverse audiences. “It is our mission to knit together the exceptional places of Essex County—the places that make this area like nowhere else—in a fun way that inspires residents and visitors to make connections between their lives and these places,” explains Annie Harris, Essex Heritage CEO. “Through programs like Trails & Sails we are enhancing tourism, building partnerships, and engaging people of all ages in sustaining the places that make this region so unique.”

This year’s event is expected to attract more than 5,000 participants who can take advantage of a variety of family-friendly activities, walks, guided hikes, paddles, historical tours, lectures, and other activities—happening morning, afternoon, and evening.  There’s an event for everyone: 

  • Outdoor Enthusiasts: Paddle at twilight on Lake Gardner in Amesbury, explore the Lynn Woods; enjoy a mindful outdoor experience at Veasey Park in Groveland, trek along the Ipswich section of the Bay Circuit Trail; set sail on the Schooner Fame in Salem or the Schooner Lannon in Gloucester, and more!
  • Fans of Walking Tours: Architecture & Social History tour in Marblehead, Bella Building Walk in Haverhill, Ellis Square tour in Beverly, History & Architecture walking tour in Manchester-by-the-Sea, Clipper Heritage Trail tour in Newburyport, Historic Essex self-guided tour in downtown Essex, Urban Walk of Historic Landmarks in Middleton, Lynn at Night walking tour, Historic Olmsted Subdivision tour in Swampscott, and more.
  • Family Fun: Explore the night sky in Amesbury, dig for history at the Rebecca Nurse Homestead in Danvers, discover invertebrates of the field and forest in Georgetown, learn about Marine Science (and why it matters) in Salem; enjoy a wilderness conservation area family stroll in Manchester; have fun at Team Haverhill’s River Ruckus in Haverhill; become a Viking on the Polaris in Salem, and take a beach walk and write poetry in Swampscott.
  • Art & Culture lovers: Take in art at the GALA (Galleries at LynnArts) plein art exhibit in Lynn, view the intersection of art & nature at the Natural State exhibition in Andover, explore outdoor sculptures in Newburyport, discover the craft of restoring old windows during the open house at the Window Woman workshop in Amesbury, learn and have fun during the Printing Arts Fair in Haverhill, and be dazzled by the St. Stephens Church stained glass windows in Lynn.

Visit to see the complete listing of events. All Trails & Sails events are free and most are available on a first-come, first-serve basis with the exception of a few reservations-required events. 

Trails & Sails 2019 is generously sponsored by Eastern Bank, Salem Five Charitable Foundation, and People’s United Bank.