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Anyone who lives on the North Shore regularly drives by historic landmarks and stunningly beautiful natural sights. Too often, though, we drive right past them, caught up in errands to run and appointments to keep.

The Essex National Heritage Area’s Trails & Sails event, celebrating its 25th anniversary this year, is designed to get locals to slow down and visit these destinations we so often pass by and so rarely explore. Over the course of sixteen days, more than two hundred planned activities will give people the opportunity to sail on a historic schooner, learn about the artists who have created in the country’s oldest working artists’ colony, search for birds in scenic and ecologically important marshes, and so much more—all free of charge. “We do this with our hosts to help residents really get outside and appreciate what’s in their own backyard,” says Cheri Grishin, director of operations for the Essex Heritage. “There are a lot of different options to choose your own adventure.”

Paddlers on a guided kayak trip, one of more than 200 free activities on this year’s schedule. Photograph By Shutterstock

The sixteen-day schedule, from September 12 to 27, includes events exploring the artistic, natural, and historic richness of the region. Essex Heritage works with host organizations to line up activities that connect to the year’s themes. This year, the event highlights Essex County’s role in the American Revolution, outdoor explorations, life by the water, and the stories we share. Trails and Sails began as one weekend, then called “Walks and Waters,” inspired by similar events organized by other national heritage areas around the country. Over the years, the Essex County events proved so popular that the schedule expanded to two full weekends as well as midweek events.

Last year, some thirty thousand people participated. This year, Grishin expects even more to show up for the slate of kayak trips, guided hikes, and vintage baseball games. “This will probably be our biggest year yet,” she says. History buffs can walk Lawrence’s Bread and Roses strike on a guided tour, or watching Revolutionary War drilling demonstrations. Art lovers can view the Depression-era murals in Marblehead’s Abbot Hall or take a sunset tour of Lynn’s hidden public art. Fans of historic buildings will have dozens to choose from, and families can make s’mores over a roaring fire, assemble a schooner collage, or identify plants and animals at a Topsfield pond.

Revolutionary-era programming is a throughline this year, from drilling demonstrations to historic house tours. Photograph Courtesy of courtesy of Essex County Greenbelt Association

Each host designs its event to reflect the distinctive ways its organization’s mission connects to the history and culture of the region. Mass Audubon’s Ipswich River Wildlife Sanctuary in Topsfield is putting on two events. The first, on September 17, is a lecture on the history of the property beginning with the first European settlers. The second, on September 19, is an evening stroll punctuated by readings of bespoke poetry written in response to the property— particularly apt because the family of Anne Bradstreet, the first published poet of Colonial America, were among the first colonists to live on the land.

Photograph Courtesy of courtesy of Essex County Greenbelt Association

Advance registration is required for both events. Participating in Trails and Sails is a natural fit for the sanctuary because it dovetails with its mission of connecting people and place, says sanctuary director Carole McCauley. “By connecting people to a sense of place, you’re more likely to love it, to want to protect it, to feel connected to it, and to feel belonging,” she says.

Photograph Courtesy of courtesy of Essex County Greenbelt Association

The North Shore Amateur Astronomy Club has hosted a Trails and Sails event for more than twenty years. Club members bring their telescopes—there were more than twenty last year—to Battis Field in Amesbury and invite guests to peer up at the heavens, checking out the craters on the moon or the rings of Saturn. This year the club will hold two “star parties,” one on September 12 and the other on September 18.

A costumed interpreter walks visitors through a colonial kitchen. Photograph Courtesy of courtesy of Essex County Greenbelt Association
Telescopes at Battis Field in Amesbury, where the astronomy club hosts two star parties this year. | Photograph by Scott Booth

“It’s really rewarding to see people experience it,” says event coordinator Brewster LaMacchia. “We’re just trying to give people an opportunity to experience something they probably haven’t experienced before and understand a little bit more about the universe.” What unites all the events and hosting organizations is a passion for showcasing the treasures of the region. “This is an opportunity to really help us fall in love with the places we live,” Grishin says.

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