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

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

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

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 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

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

SeaFestival of Trees in Salisbury

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 8:00 pm

SeaFestival of Trees in Salisbury | Saturdays

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 8:00 pm

Salem Holiday Tree Lighting

Come to the Holiday Tree Lighting in Salem to kick off the holiday season!
Join Salem Main Streets and the City of Salem as we combine two of our most beloved annual traditions – Greet Santa at the Hawthorne Hotel and the lighting of Salem’s Holiday Tree – into one evening. Santa Claus will arrive at the top of the Hawthorne Hotel (18 Washington Square W) promptly at 6:00...
5:45 pm to 6:30 pm

Greet Santa at the Hawthorne Hotel

Salem Main Streets, SalemMainStreets.org, Visit Salem MA for the holidays
Join Salem Main Streets and the City of Salem as we celebrate two of our most beloved annual traditions – Santa’s Arrival and the lighting of Salem’s Holiday Tree – all in one evening. Santa Claus will arrive at the top of the Hawthorne Hotel (18 Washington Square W) promptly at 6:00 p.m. on Friday...
5:45 pm to 8:00 pm

Beverly Tree Lighting

Beverly Massachusetts holiday tree lighting on the Common is a favorite community event!
Come to the Beverly Tree Lighting!  Gather with your neighbors and enjoy cocoa, cookies, music and Santa, as we light the town Holiday Tree!
7:00 pm

Saturday, November 29

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

Thanks for the Trails 5k

ECGA's Thanks for the Trails 5k Race on the Friday after Thanksgiving in Patton Park
ECTA is holding its 8th Annual Thanks for the Trails 5k and Kids Fun Run the Saturday after Thanksgiving at Patton Park in Hamilton (November 29, 2025).  The Kids' Run will begin at 9:30AM and the 5k will start at 10AM.  Using a scenic and challenging course and offering great prizes, this will be...
7:30 am to 11:30 am

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 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

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

Bevrec Toy Drive

Beverly Massachusetts Recreation Department hosts a holiday toy drive at Lynch Park!
The BevRec will be hosting a Holiday Toy Drive at Lynch Park to benefit the great work that Beverly Bootstraps does for our community. We’re collecting new, unwrapped toys for children of all ages to help make this season brighter for everyone in our community.
Where: Lynch Park
10:00 am to 1:00 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

SeaFestival of Trees in Salisbury | Saturdays

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 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
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