Essex Heritage Announces Plans for Trails & Sails 2026, Celebrating 25th Anniversary of History, Culture and Nature in Essex County
Trails & Sails, the beloved annual tradition and event series that invites residents and visitors to discover the history, culture, and natural beauty of Essex County, is celebrating its 25th anniversary in 2026.
This milestone year marks a shared history of community engagement, exploration, empowerment and connection with the region’s parks, waterways, historic sites and iconic cultural institutions.
What started in 2002 as a celebration of the Essex National Heritage Area has grown into hundreds of events across 34 cities and towns. All events are free, including guided hikes, behind-the-scenes tours of historic and cultural sites, boat trips, cultural celebrations, and adventures for family members of all ages.
“We’re thrilled to celebrate 25 years of Essex Heritage’s Trails & Sails. This year, we’ll be celebrating a community tradition that has connected so many people to the extraordinary landscapes and stories that define Essex County. For a quarter century, Trails & Sails has encouraged us to honor the land and sea around us, and to discover new sights in our own communities,” said Gov. Maura Healey. “As we celebrate our nation’s 250th anniversary, this moment reminds us that the spirit of 1776 persists in the landscapes we see every day.”
The slate of free events spans all 34 cities and towns in the Essex National Heritage Area. This year, as the nation commemorates America250, participants can expect to see historical reenactments, historic artisan demonstrations, interactive exhibits, and a wide variety of community-driven experiences designed for all ages and interests.
In honor of this milestone, the 2026 Trails & Sails series will feature:
- Unique programming that reflects new ways to connect with the heritage and landscapes of Essex County.
- Events that recognize the partners and community impact of the series over 25 years.
- Continued access to hundreds of free activities celebrating the region’s natural, cultural, and historic resources.
Trails & Sails will take place Sept. 12-27, 2026. Many organizations have already committed to participating this year, including Phillips Library, North Shore Concert Band, and the Merrimack Valley Bird Club. New listings are being added regularly on the Trails & Sails event calendar.
A full schedule will be available on the Trails & Sails website in the coming weeks.
“We’re thrilled to celebrate 25 years of Trails & Sails,” said Annie Harris, CEO of Essex Heritage. “This anniversary is a tribute to the countless community partners, volunteers, and participants who have helped shape this program into a vibrant showcase of the places and stories that make Essex County unique. We’re looking forward to making this year our most memorable yet.”
Since 2002, Trails & Sails has welcomed more than 175,000 visitors who have experienced the places that make Essex County special: from birdwatching on Plum Island, to exploring Den Rock Park in Lawrence, to historical sites from Saugus to Salem. The beauty and history of the Essex National Heritage Area is an incredible place to explore with your family and friends.
Lt. Gov. Kim Driscoll has experienced Trails & Sails first-hand.
“As the former Mayor of Salem, I have many memories of the Essex National Heritage Area. All across the North Shore, we have so many beautiful places to explore and for 25 years, the Trails & Sails event has helped people discover our home,” Lt. Gov. Driscoll. “With over 200 unique heritage events, Trails & Sails showcases the rich history and natural beauty that shapes our communities. Working with the Essex Heritage during my time in Salem showed me how important it is to share our region’s history, and I’m excited to count down the days to this year’s celebration.”
Bethany Groff Dorau, director of the Museum of Old Newbury (a Trails & Sails site), is a former Essex Heritage employee who helped launch Trails & Sails in 2002.
“It’s an incredible milestone!” she said. “We started with a pitch to our original sites. The original concept was so simple — do what you do best, make it free, and Essex Heritage will do the rest. It worked! And I’m so glad to see Trails & Sails going strong after all these years.”
Trails & Sails is your ticket to adventure across Essex County, Massachusetts — a region recognized as a National Heritage Area for its rich history, cultural treasures, and natural landscapes. Each September, this vibrant event series provides access to hundreds of unique experiences such as guided hikes and paddles to behind-the-scenes tours, historic reenactments, interactive exhibits, artisan demos, community celebrations, and much more. Whether you’re a history buff, nature lover, or curious to discover something new to love in your own backyard, Trails & Sails has something for everyone.
Where to learn more about Trails & Sails events
As always, all events are free to the public, though some may require advance registration. You may find them at www.trailsandsails.org or in the popular guidebook, which will be distributed in August. Both printed (8,000+ copies distributed countywide) and digital (115,000 visits in 2025) advertising with Trails & Sails is an effective way for both locals and visitors to experience all Essex County has to offer, and support its vital institutions. Advertisements start at just $300. The deadline to be included in the printed guide is June 1.
About Essex Heritage
Essex National Heritage Commission (Essex Heritage) is a non-profit organization that has been federally authorized to work in partnership to oversee the unique heritage resources of the Essex National Heritage Area. Our mission is to preserve and enhance the historic, cultural, and natural resources of the Essex National Heritage Area located in Essex County, Massachusetts. The Essex National Heritage Area was created as an act of Congress in 1996 and encompasses the 34 cities and towns of Essex County, Massachusetts. It includes two National Parks (Salem Maritime National Historic Site and Saugus Ironworks National Historic Site) and the US Parker River National Wildlife Refuge. There are also several state parks, thousands of acres of conservation land, and numerous museums, historic houses and heritage sites that are open to the public and owned/managed by non-profit organizations and municipal governments.
About Trails & Sails
Trails & Sails is an annual signature event of Essex Heritage that encourages people to explore the Essex National Heritage Area — a 500-square-mile region of extraordinary historical, cultural, and natural assets in northeastern Massachusetts. Through community partnerships, Trails & Sails offers accessible experiences that connect people with the stories, landscapes, and traditions that define the region.
