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 14-29, 2024

Gloucester Schooner Festival 2024

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 28-September 1, 2024

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

Schooner Sail on the Thomas E. Lannon

Schooner Lannon is offering a free sail - first come first served - during Trails and Sails 2019

Picture yourself relaxing on the deck of this beautiful 65- foot schooner as she sails out of Gloucester harbor on a light southwesterly breeze. Join us for a sail and get a taste for what it was like to sail on a fishing schooner a hundred years ago. Help the crew raise the sails, or just sit back and take in the sights and sounds of Gloucester’s coastline.

When: 
Saturday, September 28, 2019 11:30-1pm

USCG Tall Ship Eagle Comes to Salem!

USCG United States Coast Gaurd Cutter Barque Eagle comes to Salem Massachusetts!

The Coast Guard Barque EAGLE is making a port call in Salem, MA this August - arriving August 9 and staying through August 11!  The ship was built in 1936 in Germany, and commissioned as Horst Wessel, one of three sail training ships operated by the pre-World War II German navy. At the close of World War II, Horst Wessel was taken as a war reparation by the United States, recommissioned as the U.S. Coast Guard Cutter Eagle and sailed to New London, Connecticut. Eagle provides an unparalleled at-sea leadership and professional development experience for future officers of the U.S. Coast Guard.

When: 
Friday, August 9, 2019 Noon-7pm
Saturday, August 10, 2019 10am-2pm
Sunday, August 11, 2019 10am-7pm

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Smileland Pediatric Dental Care Waltham Malden 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

Santa at Salem Common

Come visit Santa at Salem Common in Massachusetts for a free photoshoot with your phone or camera!
Santa will be visiting the Salem Common Gazebo on Saturday, December 9th from 9:00am -12:00pm.  This event will give families the opportunity to have their picture taken with Santa and pre-bagged treats will be available for the kids.
9:00 am to 12:00 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

Santa Arrives in Marblehead

Come to Marblehead to welcome Santa as he arrives for the Christmas Walk!
Come to the State Street Landing in Downtown Marblehead to welcome Santa as he arrives by lobster boat!  There's plenty of photo ops and Santa's arrival is followed by the Marblehead Christmas Walk Parade. 
9:00 am

Music Together - Saturday

Marblehead, Beverly Farms, Hamilton, Salem, Peabody Music Together
Music Together® is a research-based music & movement program for infants, toddlers, preschoolers, and the grown-ups who love them. Music Together® classes make it easy for parents/primary caregivers to play a crucial role in activating their child's music development. Classes are 45 minutes...
9:15 am to 11:15 am

CraneOutdoors: Family Snowy Owl Prowl

Join the Trustees of Reservations at the Crane Wildlife Refuge in Ipswich Massachusetts in search of the Snowy Owl!
Wide-open coastal sites are the location of choice for wintering Snowy Owls; common perches are dunes and salt hay staddles. In winters past, these owls have been frequent visitors to the Crane Wildlife Refuge.
10:00 am to 12:00 pm

Marblehead Artisan's Holiday Marketplace

Find unique hand made gifts at Abbot Hall in Marblehead, Massachusetts - MFoA Artisans Holiday Market
The Marblehead Festival of Arts invites families to their holiday arts-and-crafts show at Marblehead Arts Association the first weekend in December. The market place is held in conjunction with the Marblehead Chamber of Commerce Marblehead Christmas Walk, a town-wide event. Each year the market...
10:00 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

Reindeer Run 5k

The Reindeer Run 5k Road Race is hosted by the YMCA of Beverly Massachusetts
Get your best reindeer on and join us as we run, walk or prance through Beverly's coastal roads and historic downtown! You may see Santa, his elves and others in festive costume…
10:00 am to 12:00 pm

Fishtown Horribles Parade of Trees

Fishtown Horribles Parade Trees, a holiday fundraiser in Gloucester Massachusetts
Gloucester's Fishtown Parade of of Trees is a community holiday fundraiser for the annual Fishtown Horribles Parade in July! Take a stroll the the Parade of Trees and find your favorites! All trees are donated and decorated by community members, businesses and organizations.
10:00 am to 5:00 pm

Tree Jubilee at Marini Farm

The Tree Jubilee hosted by Marini Farm in Ipswich  MA 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 beautifully decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! More than 50 spectacularly decorated trees...
10:00 am

Winter Wreath Making Workshop at Long Hill

Wreath Making Workshop at the Trustees of Reservations' Long Hill Garden in Beverly, Massachusetts
SOLD OUT! Learn how to craft a beautiful wreath for the holidays or for the winter season with Iris Weaver!
10:00 am to 12:00 pm

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Come to Hammond Castle for the 6th annual Deck The Halls holiday celebration. Hammond Castle Museum will be dressed for the holidays inside and out. Delight in the enchanting ambiance of Christmas and White Birch trees, meticulously arranged garlands, festive wreaths, and the warm embrace of...
10:00 am to 4:00 pm

Children's Holiday Party with the Snow Sisters at IPL

Children's Holiday Party with the Snow Sisters at the Ipswich Public Library in Massachusetts!
Join IPL children’s librarians for a fun-filled morning to get you in the holiday spirit with a visit from the Snow Sisters along with crafts and refreshments!
10:00 am to 12:00 pm

2024 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

Natural Wreath Making Workshop | Appleton Farms

Come to Appleton Farms in Ipswich Massachusetts to make your own Holiday Wreath!
Decorate your door with a gorgeous holiday wreath, created from a variety of textural evergreen boughs all foraged from our historic farm property! Join us in our historic barn where we will demonstrate a simple technique for making your wreath. You will then have the opportunity to make your...
10:00 am to 1:30 pm

A Colorful Christmas at Castle Hill

A Colorful Christmas by the Sea 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 Travels with the Cranes. Each room in our 1920s mansion is decorated for the holidays drawing inspiration from Crane travels around the world, including Paris, Japan, Egypt, and New York.
10:00 am to 8:00 pm

Predator vs. Prey | Family Nature Series

Essex County Greenbelt teams up with North Shore Nature Programs for a wildlife hike in Ipswich Massachusetts!
Look for signs of our local predators on the prowl and learn about how prey animals have evolved to evade them in this family-friendly walk. Appropriate for all ages - we’ll talk scientifically about what types of animals are predators or prey, without going into especially gory details.
10:30 am to 12:00 pm

Christmas in Salem House Tour

Tour some of Salem Massachusetts' historic houses all done up for the Holiday and raise funds for a worthy local cause
Historic Salem, Inc. hosts its annual holiday house tour in downtown Salem Massachusetts! Few communities have the rich legacy of historic houses that Salem, Massachusetts boasts. These homes, spanning four centuries, help define the character as well as the appearance of the city.  Every year...
10:30 am to 4:30 pm

NEER North Holiday Open House

NEER North Holiday open house to celebrate the holidays and with our adopted animals!
NEER North invites you to their Holiday Open House! Swing by NEER North for our fourth annual Holiday Open House event.
Where: NEER North
11:00 am to 2:00 pm

Lowell's Boat Shop Holiday Open House

Visit Lowell's Boat Shop in Amesbury Massachusetts for their annual holiday open house!
Visit Lowell’s Boat Shop during their Annual Holiday Open House is a two day family event during the first weekend in December. See the shop transformed with beautiful trees, an art show, silent auction, Nautical Gift Shop, Lowell’s gear to wear, books, glassware, and more. Make it a day! Live...
11:00 am to 4:00 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. The fantastic lights downtown, the tree in Market Square, all the beautifully decorated window boxes and of course, Santa's Workshop, where the kids can whisper their wishes to Santa.
11:00 am to 2:00 pm

Christmas Tea at the Phillips House

Celebrate the season with a Holiday Tea at the Phillips House in Salem Massachusetts
Celebrate the season with Christmas Tea at Phillips House! Enjoy a festive tea with tea sandwiches and sweet treats in beautiful Samuel McIntire-designed rooms.
11:00 am to 4:00 pm

Holiday Market in the Shipyard

Shop Local and stuff your stockings with unique gifts from curated vendors at the Essex Shipbuilding Museum in Massachusetts
Head over to the Essex Shipbuilding Museum and the historic schoolhouse at 28 Main Street for unique local holiday gifts!
11:00 am to 3:00 pm

Marblehead Christmas Walk Parade

The Christmas Walk parade in Marblehead Massachusetts is a a holiday tradition for the entire town!
The Marblehead Christmas Walk Parade takes place after Santa Arrives in Marblehead. The Parade begins at 11:45 and the route takes approximately one hour, traveling from Front St., State St., Washington St., Five Corners, Atlantic Ave. Gerry Street, down Pleasant St. and concluding at the National...
11:45 am

Santa’s Arrival & Tree Lighting in Rockport

Santa comes to Rockport Ma by lobster boat to kick off the Holiday season in Rockport Massachusetts!
Where else can you see Santa arrive by lobster boat? Santa will arrive at Rockport’s T-Wharf on Rockport Harbor following a brisk lobster boat ride across Sandy Bay. Then Santa will climb up onto a Rockport Forest Fire truck and proceed along T-Wharf and Broadway to the First Baptist Church, led by...
12:30 pm to 5:00 pm

Native Seed Sowing at Long Hill

Seed Sowing Woirkshop at The Trustess of Reservations' Long Hill Gardens in Beverly Massachusetts
Sold Out! Join Erin Hammes, Plant Records and Production Horticulturist at Native Plant Trust, for this native seed sowing workshop. Learn about our native seeds and then get your hands in the soil to sow some seeds that you can take home.
1:00 pm to 2:30 pm

Santa-by-the-Sea!

Santa will arrive at Masconomo Park by lobster boat at 1 pm on December 2, 2017
Come to the the annual Jingle Bell Walk in Manchester! Santa will arrive at Masconomo Park by boat and lead the children in a parade around the park and then be available for pictures. There will also be a petting zoo, crafts, face painting, a candy cane hunt, refreshments and a visit from Mrs.
1:00 pm to 3:00 pm

CraneOutdoors: Sunset Hike to Cedar Point

Sunset hike to Cedar Point at the Trustees Crane Estate in Ipswich Massachusetts
The Trustees of Reservations invite you to a sunset hike at the Crane Estate in Ipswich,Massachusetts. There’s no better excuse to explore Cedar Point—the western-most part of the Crane Estate—than a hike at sunset. This two-hour adventure in a lesser-known part of the property has it all…
2:00 pm to 4:00 pm

Amesbury Holiday Parade

Enjoy the tradition of the Amesbury Massachusetts Holiday parade with your family!
Enjoy the tradition of the Amesbury Massachusetts Holiday parade with your family! This year’s theme for the Amesbury Holiday Parade is Musical Notes and Holiday Floats. The parade will begin at 3:30pm from the intersection of Sparhawk and Greenleaf Street, and finish up with the Amesbury Holiday...
3:30 pm to 5:00 pm

Trustees Winterlights at Stevens Coolidge Place

The Trustees of Reservations Winterlights at the Stevents-Coolidge Place North Andover North Andover.
Winterlights is back! Join the Trustees for a magical outdoor experience at Stevens-Coolidge House & Gardens, and see the gardens aglow with your favorite light installations as well as marveling at new components. Bring the whole family for a fun and safe outdoor experience. Winterlights runs...
4:30 pm to 8:00 pm

Rowley Tree Lighting on the Common

Come to the Town Common in Rowley Massachusetts for the annual holiday tree lighting
The Rowley Girl Scouts and RMLP look forward to seeing you at Rowley Town Common for the Lighting of the Common at 4:30pm. Caroling, cocoa, cider and candy canes and genuine Hallmark small town vibes.
4:30 pm

Sunday, December 8

ECGA Mutt Strut

Hike Thompson Street Reservation in Gloucester Massachusetts with your dog and the ECGA!
An adventurous outing for you and your pup! Tompson Street has a little of everything: wooded trails, bridges across the swamp, rocky outcroppings…! The dogs and humans have a blast! Social dogs very, very welcome!
1:30 am to 3:30 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

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

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

A Colorful Christmas at Castle Hill

A Colorful Christmas by the Sea 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 Travels with the Cranes. Each room in our 1920s mansion is decorated for the holidays drawing inspiration from Crane travels around the world, including Paris, Japan, Egypt, and New York.
10:00 am to 8:00 pm

2024 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

Marblehead Artisan's Holiday Marketplace

Find unique hand made gifts at Abbot Hall in Marblehead, Massachusetts - MFoA Artisans Holiday Market
The Marblehead Festival of Arts invites families to their holiday arts-and-crafts show at Marblehead Arts Association the first weekend in December. The market place is held in conjunction with the Marblehead Chamber of Commerce Marblehead Christmas Walk, a town-wide event. Each year the market...
10:00 am to 5:00 pm

Tree Jubilee at Marini Farm

The Tree Jubilee hosted by Marini Farm in Ipswich  MA 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 beautifully decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! More than 50 spectacularly decorated trees...
10:00 am

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Come to Hammond Castle for the 6th annual Deck The Halls holiday celebration. Hammond Castle Museum will be dressed for the holidays inside and out. Delight in the enchanting ambiance of Christmas and White Birch trees, meticulously arranged garlands, festive wreaths, and the warm embrace of...
10:00 am to 4:00 pm

CraneExplorer: Shipwreck Scholars

Families learn about shipwrecks at Castle Hill and Crane Beach in Ipswich Massachusetts
Coastal views with a side of shipwreck! Families will be guided on a Castle Hill hike through the salt marsh, dunes, and beach, while learning about local nautical history, including the role of Fox Creek Canal and Robinson Boat Yard in the area’s shipbuilding legacy, and the fascinating tale of...
10:00 am to 12:00 pm
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