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

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

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

Pages

Summerquest Camp for kids aed 5-14 at the Crane Estate in Ipswich 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

Maudslay in Bloom Self-Guided Walk

 Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
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

The Lady of Salem: Maritime Art

Learn about the history of Salem Massachusetts through this unique public art installation self-guided tour!
Discover Salem’s Golden Age of Sail as you uncover clues! Celebrate America’s Maritime History! The Ladies of Salem will have you looking up at whimsical and beautifully designed figureheads gracing lampposts downtown. “What is a figurehead ?” you may ask? It’s a large carved wooden decorative...
8:00 am to 10:00 pm

Rockport Farmers' Market

The Rockport Farmers' Market runs every Saturday at Rockport Music in Downtown Rockport!
The Rockport Farmers Market offers a variety of locally-grown produce, hand-crafted products, baked goods, and live music. It provides a community space to support local farmers and artisans.
9:00 am to 1:00 pm

Haverhill Farmers' Market

Haverhill Farmers Market, North Shore Farmers Market, Cape Ann Farmers Marke
The vibrant, colorful Haverhill Farmers Market is where local farmers and food producers meet to sell directly to the community. Established in 1978, the Haverhill Farmers Market mission is to provide access to farm-fresh products and promote local agriculture, as well as serve as a social...
9:00 am to 1:00 pm

Crescent Farm Corn Maze

Crescent Farm corn maze in Haverhill Massachusetts
Imagine the biggest puzzle you’ve ever seen. Now imagine a day in the sunshine with your friends or family. Now add an adventure that takes teamwork and memory skills. All these things and more can be found at Crescent Farms Corn Maze. Crescent Farm Corn Maze trails cut into 9 acres of corn. Inside...
9:00 am to 9:00 pm

Marblehead Farmers' Market

Find fresh local produce and other foods at the Marblehead Farmer's Market!
The Marblehead Farmer's Market boasts 15+ local farms, and booths with an educational spin nutrition, vendors and farms selling homemade prepared goods and craft vendors that are switched up in a rotation basis week to week. Additionally there are entertainers and exhibits by environmentally...
9:00 am to 12:00 pm

Andover Farmers' Market

Find Fresh Local Produce at the Andover Massachusetts Farmers Market North of Boston
The Andover Farmers Market is a vibrant hub connecting local farmers, artisans and the community through the joy of local food. Whether you come for carrots or conversation, it is a place to nourish the body, mind and spirit.
9:00 am to 1:00 pm

Music and Movement at North Shore Children's Museum

North Shore, North Shore Childrens Museum in Peabody MA
Music and Movement with Marybeth Maes is an engaging music and movement class for young children at the North Shore Children's Museum. Marybeth brings her guitar and instruments for the children to use while they sing, dance, and play.
10:00 am to 11:00 am

Doggy Maze Daze at Marini Farm

Marini Farm in Ipswich is teaming up with the Ipswich Humane Group to host a Doggy Maze Daze Fundraiser.
The Ipswich Humane Group is teaming up with Marini Farm in Ipswich to host a Doggy Maze Daze Fundraiser to support the Ipswich animal shelter. One weekend only Marini Farm will open the corn maze for pet owners and their four legged friends! Guests can bring their canine companions and get lost in...
10:00 am to 6:00 pm

Saugus Iron Works House Tours

Free Ranger guided tours of the Saugus Iron Works House in Massachusetts
Join National Park staff at Saugus Iron Works National Historic Site for a 30-minute tour of The Iron Works House.
11:00 am

Boat Tour to Misery Island

Journey on Essex Heritage’s landing craft Naumkeag to Great Misery Island in Salem Sound Massachusetts
Journey on Essex Heritage’s landing craft Naumkeag to Great Misery Island in Salem Sound. Along the way, hear stories about the rich history of the harbor and how the Misery Islands acquired their unique name. When you arrive, you’ll have 2 hours to explore the trails, open meadows, rocky shoreline...
11:00 am to 2:00 pm

Long Hill Garden Tours

Tour the Gardens at the Trustees of Reservations Long Hill Gardens in Beverly, Massachusetts!
The Trustees of Reservations invite you to join our expert guides for a tour around Long Hill’s stunning Sedgwick Gardens and learn more about the special plants. Visit Long Hill’s breathtaking gardens and stately historic house for a guided tour. Enjoy the rich history of this grand country estate...
11:00 am to 12:00 pm

Saugus Iron Works Tours

Free Ranger guided tours at Saugus Iron Works Colonial Industrial Site in Massachusetts
Join the National Park staff at Saugus Iron Works National Historic Site for a tour of the colonial industrial site. On select days, you may be able to stick around and witness pop-up molten iron pour, blacksmithing, waterwheel demonstrations, and take part in hands-on river stewardship activities.
2:00 pm

Sunday, September 7

Todd Farm Market

Come to Todd Farm on Sunday - A classic New England Fleas Market in Rowley Massachusetts!
From early Spring to late Fall, Todd Farm is a great Sunday destination for families!  Head to the farm and explore the outdoor award-winning Market featuring up to 240 vendors from all over New England and New York!
5:00 am to 3:00 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

Maudslay in Bloom Self-Guided Walk

 Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
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

The Lady of Salem: Maritime Art

Learn about the history of Salem Massachusetts through this unique public art installation self-guided tour!
Discover Salem’s Golden Age of Sail as you uncover clues! Celebrate America’s Maritime History! The Ladies of Salem will have you looking up at whimsical and beautifully designed figureheads gracing lampposts downtown. “What is a figurehead ?” you may ask? It’s a large carved wooden decorative...
8:00 am to 10:00 pm

Newburyport Farmers' Market

Newburyport Farmers find organic locally grown produce, meat, dairy Newburyport
The Newburyport Farmers Summer Market celebrates local fresh produce every Sunday morning rain or shine!  Start your Sunday browsing fresh North Shore local produce, meats, cheeses, and seafood in an open air market atmosphere! Food and beverage vendors offer fresh hot coffee, breakfast treats and...
9:00 am to 1:00 pm

Crescent Farm Corn Maze

Crescent Farm corn maze in Haverhill Massachusetts
Imagine the biggest puzzle you’ve ever seen. Now imagine a day in the sunshine with your friends or family. Now add an adventure that takes teamwork and memory skills. All these things and more can be found at Crescent Farms Corn Maze. Crescent Farm Corn Maze trails cut into 9 acres of corn. Inside...
9:00 am to 9:00 pm

Rowley Farmers Market

Rowley Farmers Market - a seasonal open-air market every Sunday July-September on Rowley Common
The Rowley Farmers Market is an open air market held on Sundays on the Rowley Town Common.  There's always a great selection of fresh local produce, food stuffs and locally hand-made goods. Come pick up some great locally grown food, freshly baked bread by Faith Anne's Unique bread, specialty teas...
9:00 am to 1:00 pm

Marini Farm Corn Maze

The 2025 Marini Farm Corn Maze in Ipswich Massachusetts is themed for The Wizard of Oz
Come to Marini Farm for a fun journey through our corn maze! The Maze Park, corn maze, farm stand, bakery and other attractions provide a great destination for kids birthday parties, school trips, corporate team building, scout outings, and family activities. Marini Farm is located in beautiful...
10:00 am to 10:00 pm

Doggy Maze Daze at Marini Farm

Marini Farm in Ipswich is teaming up with the Ipswich Humane Group to host a Doggy Maze Daze Fundraiser.
The Ipswich Humane Group is teaming up with Marini Farm in Ipswich to host a Doggy Maze Daze Fundraiser to support the Ipswich animal shelter. One weekend only Marini Farm will open the corn maze for pet owners and their four legged friends! Guests can bring their canine companions and get lost in...
10:00 am to 6:00 pm
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