Sailing

Trails & Sails

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

Essex National Heritage Area sites will offer over 150 free family fun events from September 14-29, 2024 for the annual celebration of TRAILS & SAILS. Discover special places in your backyard and be guided through unique landscapes on land and sea, explore historic properties, and take in cultural experiences of all kinds. Find what makes Essex County like nowhere else during Trails & Sails! It’s all FREE and it’s all located within the 34 cities and towns of Essex County.

When: 
Daily, September 13-28, 2025

Open Boarding on the Hannah (AKA the Fame)

Board Schooner Fame at the waterfront in Marblehead Massachusetts as part of trails and sails!

The Hannah, the first of several schooners commissioned by General George Washington, began her career as an armed cruiser in September 1775. To commemorate that important part of Marblehead’s history, the Fame – similar in size and appearance to the Hannah (aka Schooner Fame)– will be docked at Marblehead’s Town Landing from 9:00 am to 10:15 am on Saturday, September 20th, and Sunday, September 21st.

When: 
Saturday, September 20, 2025 9-10:15am
Sunday, September 21, 2025 9-10:15am

Gloucester Schooner Festival 2025

The Gloucester Schooner Festival celebrates maritime, sailing and fishing heritage of Cape Ann Massachusetts

The Gloucester Schooner Festival is a  wonderful celebration of Gloucester's fishing and maritime history during labor day weekend. This year's festival, hosted by Maritime Gloucester, is Gloucester’s major marine event, with participating vessels coming from ports along the Eastern seaboard and beyond. There will be both large and small vessels—ranging from 19 feet to over 100 feet in length. You will see new boats and old boats, from newly built (Ardelle - launched 2011) to over 100 years old!

When: 
Labor Day Weekend, August 27-31, 2025

Marine Society Outings on the Schooner FAME

Schooner Fame's Marine Society Outings are designed for children ages 8-14 out of Salem Massachusetts

Marine Society Outings are designed for children ages 8-14. Each outing is five hours on the water, 9:00-2:00, usually with a stop at the islands to swim off the boat (swimming is optional). Participants raise and trim the sails, learn knots, steer the boat, and play silly camp games. We accept 16 kids per session. Cost is $85. For Salem residents the cost is just $55, thanks to the Marine Society! In the event of bad weather, Outings may be postponed to the next day, or cancelled, in which case you will receive a refund.

When: 
Wednesday, August 6, 2025 9am-2pm
Location: 

Schooner Ardelle Date Night

Schooner Ardelle turns into the love boat for date night sailing out of Gloucester Massachusetts!

Maritime Gloucester and  Schooner Ardelle have teamed up to create Date Night! Schooner Ardelle becomes the 'Love Boat' for moms and dads, while kids (ages 5-11) enjoy the care of the staff at Maritime Gloucester, the aquarium and lots of fun activities. You'll have a nice romantic sail around Gloucester with a cocktail, and can rest easy knowing that your child is happy and engaged with a trusted team of professionals!

When: 
Friday, June 21, 2024 6-8pm
Friday, July 26, 2024 6-8pm
Friday, August 23, 2024 6-8pm

Kids Sail Free on Schooner Adventure!

Schooner Adventure in Gloucester Massachusetts announces free sailing for kids in 2022!

Schooner Adventure in Gloucester Massachusetts offers free sailing for kids in 2024!* Sail into history on Gloucester's flagship vessel, a National Historic Landmark and icon of the American fisheries. Enjoy an engaging sail on historic Gloucester Harbor, America's oldest fishing port.  Help the crew raise the sails, take a turn at the helm, learn about Adventure's legacy and restoration, or sit back and enjoy the iconic sites of Gloucester Harbor.

When: 
Fridays July 5, 12 & 19, 2024 Times Vary - Check Calendar
Sundays through June 30 - July 21, 2024 Times Vary - Check Calendar

Gloucester Maritime Rendezvous

The Gloucester Maritime Rendezvous celebrates its combined heritage with Lunenburg Nova Scotia

The Gloucester Maritime Rendezvous celebrates the combined heritage of two great fishing towns and their connection to the sea. Gloucester, Massachusetts and Luneburg, Nova Scotia. In this annual tradition, once more the Gloucester International Dory Racing Committee hosts the Canadian Dory Rowing Association from Nova Scotia to compete against the best dory rowers from Gloucester, going head-to-head on Gloucester's historic harbor.  Boat tours and deck tours happen daily and there are many opportunities available to sail aboard the particitpating vessels!

When: 
July 6-9, 2023

War of 1812 Bicentennial

Come to Salem Maritime to celebrate the Bicentennial of the War of 1812!

War of 1812 Day at Salem Maritime National Historic Site! Salem Maritime will be celebrating the Bicentennial of the War of 1812 with living history programming throughout the day. Meet some of Salem's 19th century citizens, and hear their views on this controversial war. Family activities and Junior Ranger programs will be offered all day.

When: 
Saturday, September 29, 2012 10am-4pm

Pages

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

Marblehead Christmas Walk

The Marblehead Christmas Walk is several days of local Holiday events in Marblehead Massachusetts
The Marblehead Chamber of Commerce invites you to Marblehead to enjoy several days of holiday festivities, family events and activities!  Come for one or all days with highlights that include Santa's arrival by lobster boat,Festive shopping, Tree Lightings, a holiday parade, Artisan Markets,...
9:00 am to 9:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
9:00 am to 5:00 pm

Family & Friends CPR Course

Learn about infant and child cpr and choke saving skills at Beath Israel Lahey Health's Beverly Hospital in Massachusetts!
It is only a matter of a few short minutes before it is too late to save a life … learning what to do provides you precious minutes and gives someone a chance to survive.  The Family & Friends CPR Course teaches the lifesaving skills of child CPR with breaths, child AED use, infant CPR, and m
10:00 am to 12:00 pm

2025 Marblehead Gingerbread Festival

The Marblehead Gingerbread Festival is part of the Marblehead Chamber of Commerce's Christmas Walk, and the proceeds will go to benefit the Marblehead Family Fund and the Marblehead Historical Society.
Come see over 100 locally and professionally made gingerbread creations on display at the historic Jeremiah Lee Mansion in Marblehead, MA during this year's Marblehead Christmas Walk. Community members, businesses, and families are building and donating dozens of gingerbread houses, boats and local...
10:00 am to 4:00 pm

Tree Jubilee at Marini Farm

The Tree Jubilee hosted by Marini Farm in Ipswich Massachusetts is a fun and unique charity event!
Come to Marini Farm for the Tree Jubilee fundraiser to benefit The Ipswich Humane Group.  Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and...
10:00 am

Christmas at Castle Hill | A Nod to Nature

Christmas at Castle Hill | A Nod to Nature is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
10:00 am to 8:00 pm

SeaFestival of Trees | Santa & Grinch Brunch

Brunch with Santa and the Grinch at the Sea Festival of Trees in Salisbury Massachusetts
Red Suit. Green Suit. Jolly one. Mean one. Who’s your fave? Santa or The Grinch. Come join the holiday fun in Beach-Ville! Here’s what’s happening:
10:00 am to 12:00 pm

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
10:00 am to 8:00 pm

Santa's Workshop

Santa's Workshop in Newburyport, Massachusetts. Visit Newburyport MA during the holidays
Newburyport is a favorite local town to shop - especially during the holidays. Bring the family to Newburyport to visit Santa in his traditional workshop, share your wish list, and snap a photo with Mr. Claus!
11:00 am to 2:00 pm

SeaFestival of Trees | Sundays

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 5:00 pm

CraneOutdoors: Family Winter Wildlife Walk

Come explore the dunes on Castle Neck and Crane Beach in Ipswich Massachusetts to learn about winter wildlife.
A CraneOutdoors Family Winter Wildlife Walk will take you on a stroll through the Crane Beach dunes while learning about the plants and animals that call this special place home. You may be familiar with Crane Beach, but have you ever visited the dune trails? The dunes of Castle Neck are a much...
1:00 pm to 3:00 pm

Take a Trolley Ride with Scrooge!

Salem Trolley Christmas Carol, Fun Holiday Events north of Boston, Trolley Ride with Scrooge
Join Scrooge on the Salem Trolley as you ride through Salem Massachusetts in this rolling production performed by the Griffen Theater . Now entering into it's 39th Season, this humorous & whimsical interactive performance reanimates Dickens’ timeless seasonal holiday classic. Experience...
2:00 pm to 9:30 pm

Sunday STEAM Club at North Shore Children's Museum

Visit Peabody MA, NorthShore, North Shore Children's Museum
Join in on Sundays at 2:30 for STEAM Club for ages 5-11. Each week participants will explore science, technology, engineering, art, and math with our NSCM staff! Every STEAM club session will see your kids participating in hands-on activities while exploring a new topic. Space is limited, please...
2:30 pm to 4:00 pm

Gloucester's Santa Parade & Tree Lighting

Santa will come to Gloucester to launch the Christmas Parade and Tree Lighting -
Gloucester's Holiday Parade is a great tradition to kick off the holidays! Come enjoy the parade, Santa, and the tree lighting at Kent Circle!  Volunteers will line up parade participants at the State Fish Pier on Parker Street at 2:00 PM and will guide them through downtown Gloucester and on to...
3:00 pm to 5:00 pm

Monday, December 8

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
9:00 am to 5:00 pm

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 10am 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

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
10:00 am to 8:00 pm

Take a Trolley Ride with Scrooge!

Salem Trolley Christmas Carol, Fun Holiday Events north of Boston, Trolley Ride with Scrooge
Join Scrooge on the Salem Trolley as you ride through Salem Massachusetts in this rolling production performed by the Griffen Theater . Now entering into it's 39th Season, this humorous & whimsical interactive performance reanimates Dickens’ timeless seasonal holiday classic. Experience...
2:00 pm to 9:30 pm

Tuesday, December 9

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Salem Witch Hunt Walking Tour

Learn about the true reality of the Salem Massachusetts Witch Trials Salem Massachusetts on a self guided walking tour with Essex Heritage
This self-guided walking tour is designed to help explain the true history behind the Salem Witch Trials. After more than three centuries of storytelling through countless books, movies, and television shows, the line between historical fact and dramatic fiction has become increasingly blurred....
9:00 am to 5:00 pm

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
10:00 am to 8:00 pm
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