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
MarketStreet Lynnfield, Market Street Lynnfield The best events for families.

MarketStreet Lynnfield Outdoor Ice Skating and Warming Tent

Outdoor Ice Skating and Warming Tent at MarketStreet Lynnfield
MarketStreet Lynnfield will once again welcome guests to celebrate the magic of the winter season with the return of The MarketStreet Rink sponsored by Capital One.

Parent & Child Bachelor's Buttons Classes

Parent & Child Classes at Waldorf at Moraine Farm - Beverly MA
Bachelor’s Button is a full year pre-nursery program for caregiver and child 2 1/2 – 3 1/2 years of age. We have two Bachelor’s Buttons classes that meet weekly on Mondays and Tuesdays, September through June, from 9:00 to 11:30 am. Classes follow the Waldorf School at Moraine Farm schedule. 30...
9:00 am to 11:30 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

Homeschool Winter and Spring Sessions Registration Open

Waldorf at Moraine FArm Homeschool Winter and Spring Sessions
Waldorf Homeschool Program - Academic and Artistic Enrichment Classes for Homeschooled Students – First through Eighth Grade Level Classes Waldorf School at Moraine Farm is pleased to announce registration is open for the Homeschool Program on our beautiful Beverly, Massachusetts campus.
10:00 am to 12:00 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

Color Me Tuesdays at Growing Smile Pediatric Dentristry - Peabody

Growing Smile Pediatric Dentistry and Braces in Peabody MA
Need something fun to do this summer? We've got you covered! Stop by Growing Smiles Pediatric Dentistry and Braces every Tuesday for a different coloring activity. Every Tuesday at 3pm.
3:00 pm to 4:00 pm

Wednesday, January 22

MarketStreet Lynnfield Outdoor Ice Skating and Warming Tent

Outdoor Ice Skating and Warming Tent at MarketStreet Lynnfield
MarketStreet Lynnfield will once again welcome guests to celebrate the magic of the winter season with the return of The MarketStreet Rink sponsored by Capital One.

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

Homeschool Winter and Spring Sessions Registration Open

Waldorf at Moraine FArm Homeschool Winter and Spring Sessions
Waldorf Homeschool Program - Academic and Artistic Enrichment Classes for Homeschooled Students – First through Eighth Grade Level Classes Waldorf School at Moraine Farm is pleased to announce registration is open for the Homeschool Program on our beautiful Beverly, Massachusetts campus.
10:00 am to 12:00 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

Greater Newburyport Children's Chorus Spring Semester Auditions

Greater Newburyport Children's Chorus Spring Semester Auditions at Hope Church
The Greater Newburyport Children's Chorus is holding open auditions for singers currently in grades 4-8. The auditions are held in groups of up to 4 singers and do not require any musical preparation. Singers will be asked to sing familiar tunes, such as 'Happy Birthday'.
5:00 pm to 6:00 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, January 23

MarketStreet Lynnfield Outdoor Ice Skating and Warming Tent

Outdoor Ice Skating and Warming Tent at MarketStreet Lynnfield
MarketStreet Lynnfield will once again welcome guests to celebrate the magic of the winter season with the return of The MarketStreet Rink sponsored by Capital One.

River Valley Charter School Parent Information Sessions and School Tours

River Valley Charter School - Newburyport
River Valley Charter School invites parents to attend one of its Parent Information Sessions and School Tour to learn how RVCS is a good fit for your family. Learn about how to apply for the 2020-2021 school year enrollment lottery. RVCS provides a rigorous academic program based on the Montessori...
9:00 am to 10:00 am

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