Trails & Sails 2019

Explore the North Shore with over 150 Free Events in Essex National Heritage Area's Trails & Sails celebration.

Essex National Heritage Area sites will offer over 150 free family fun events from September 20-29, 2019 for the annual celebration of TRAILS & SAILS. Participants can hike, bike, paddle, stroll or sail through the region and Essex National Heritage Area will provide a passport to fun and adventure. It’s all FREE and it’s all located within the 34 cities and towns of Essex County.

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.

Printed Guides

Although you can check events and create your own itinerary online, a limited number of printed guides will be available for FREE at Essex National Heritage Area Regional Visitor Centers, and Eastern Bank and locations in Essex County, MA. The guides will be available after Labor Day (after September 2, 2019). Before you go, we recommend that you call ahead to check hours and to confirm that guides are still available.

Most events will accommodate between 12 and 50 participants on a first-come, first-served basis, with the exception of a few reservation-required events. Here is the lineup of all 2019 events

Watch our site for our favorite upcoming Trails & Sails 2019 events!

When: 
Daily, September 20-29, 2019
Prices: 
Free
Phone: 
978.740.0444
Harborlight Montessori School - Infant to Grade 8 - Beverly MA

Massive Spring and Summer Children's Consignment Event

Massive Spring and Summer Children's Consignment Event
Don't miss the Children's Drop and Shop Spring and Summer consignment sales event at Pingree School, Hamilton MA, for name brand children’s clothing, toys, gear and furniture. Shop for the best bargains on new & gently used Spring and Summer children's clothing, brand name toys and gear,...

Dog Friendly Shops at MarketStreet Lynnfield

Dog Friendly Shops and Restaurants at MarketStreet Lynnfield
Animal lovers will be glad to learn MarketStreet Lynnfield has over 40 shops and restaurants that are dog-friendly. Use #PupsOfMarketStreet on social media when you are there with your four-legged friend to get a free treat at PolkaDog Bakery. Enjoy!
10:00 am to 9:00 pm

Arts and Crafts for Little Ones with Colleen Apostolos

Art Classes for children with Colleen Apostolos
Certified Montessori teacher, artist and local mother, Colleen Apostolos-Marsh will guide your young artist in an exploration of color, shape, and texture. Using a variety of media, your child will be free to express their in a beautiful space while socializing and engaging in cooperative play....
10:15 am to 11:15 am

AJH: Mother & Baby Newborns: 0-6 Weeks

Mother and Baby, Newborn Support Groups aAnna Jaques Hospital
MOTHER & BABY GROUPS Anna Jaques Hospital is pleased to offer free group classes for all mothers in our community to provide support, encouragement and advice on parenthood and questions that arise after going home. This new group (for moms, grandmothers, and female caregivers only) is focused...
2:00 pm to 3:30 pm

Stargazing at Mendel Observatory

Mendel Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night
The Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night (weather permitting) starting at dusk or 7 p.m., whichever is later.  When special astronomical events of interest occur (total lunar eclipses, etc.) the Obse
7:00 pm

Thursday, July 16

Massive Spring and Summer Children's Consignment Event

Massive Spring and Summer Children's Consignment Event
Don't miss the Children's Drop and Shop Spring and Summer consignment sales event at Pingree School, Hamilton MA, for name brand children’s clothing, toys, gear and furniture. Shop for the best bargains on new & gently used Spring and Summer children's clothing, brand name toys and gear,...

Sing & Dance with the Music Man

Sing & Dance with the Music Man Brian Doser in Hamilton visit Massachusetts
Come join the fun at Community House Of Hamilton & Wenham Monday, Thursday, and Saturday mornings at 10 a.m. for 30 - 45 minutes of great music with Brian Doser! Sing and dance with the Music Man during a family concert, featuring familiar and original tunes, performed by local dad and musician...
10:00 am to 10:45 am

Dog Friendly Shops at MarketStreet Lynnfield

Dog Friendly Shops and Restaurants at MarketStreet Lynnfield
Animal lovers will be glad to learn MarketStreet Lynnfield has over 40 shops and restaurants that are dog-friendly. Use #PupsOfMarketStreet on social media when you are there with your four-legged friend to get a free treat at PolkaDog Bakery. Enjoy!
10:00 am to 9:00 pm

Arts and Crafts for Little Ones with Colleen Apostolos

Art Classes for children with Colleen Apostolos
Certified Montessori teacher, artist and local mother, Colleen Apostolos-Marsh will guide your young artist in an exploration of color, shape, and texture. Using a variety of media, your child will be free to express their in a beautiful space while socializing and engaging in cooperative play....
10:15 am to 11:15 am

Cape Ann Farmers' Market

The Cape Ann Farmers Market will be drive thru and pre-order only for the 2020 season
For the 2020 Season, Cape Ann Farmers Market will hold a Drive Thru/Pre-Order market. As things develop the Market organizer will do their best to work through the hurdles please visit the website and facebook page frequently for updated information!
3:00 pm to 6:30 pm

Salem Farmers' Market

The Salem Farmer's Market bring the goodness of local farm to downtown Salem!
The Salem Farmers' Market brings fresh local produce and other foods from North Shore farms and other local resources to downtown Salem every Thursday at Derby Square on Front Street Bentley Academy Charter School! Due to COVID-19, the market has needed to make some adjustments please read their...
3:00 pm to 7:00 pm

Friday, July 17

Massive Spring and Summer Children's Consignment Event

Massive Spring and Summer Children's Consignment Event
Don't miss the Children's Drop and Shop Spring and Summer consignment sales event at Pingree School, Hamilton MA, for name brand children’s clothing, toys, gear and furniture. Shop for the best bargains on new & gently used Spring and Summer children's clothing, brand name toys and gear,...

Farm Friends

Farm Friends a program for preschoolers at Spencer Peirce Little Farm Newbury Massachusetts!
Children three to six and a favorite adult of their choosing are invited to share in some fun-filled farm adventures which will connect them to daily life at Spencer Peirce Little Farm.
10:00 am to 11:00 am

Dog Friendly Shops at MarketStreet Lynnfield

Dog Friendly Shops and Restaurants at MarketStreet Lynnfield
Animal lovers will be glad to learn MarketStreet Lynnfield has over 40 shops and restaurants that are dog-friendly. Use #PupsOfMarketStreet on social media when you are there with your four-legged friend to get a free treat at PolkaDog Bakery. Enjoy!
10:00 am to 9:00 pm

Arts and Crafts for Little Ones with Colleen Apostolos

Art Classes for children with Colleen Apostolos
Certified Montessori teacher, artist and local mother, Colleen Apostolos-Marsh will guide your young artist in an exploration of color, shape, and texture. Using a variety of media, your child will be free to express their in a beautiful space while socializing and engaging in cooperative play....
10:15 am to 11:15 am