Trails & Sails 2025

Fair in the Square

Fair in the Square is a Salisbury Days event in the middle of Salisbury Massachusetts

Fair in the Square is a time- honored tradition celebrating each other and showcasing our charming  town. Come shop local vendors and makers offering a wide variety of goods from local honey and bee related products to jewelry to facepainting to artists and more!

When: 
Sunday, September 21, 2025 10am-4pm

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 three dimensional representation of a person, animal or mythical creature located at the bow (forward part) of a sailing ship. They were thought to bring good luck as the “eyes” of the ship. Each “Lady” has a unique story to tell. Just head to Destination Salem Visitors Center on Derby Street to pick up the scavenger hunt, and use QR codes to find the lady locations!

When: 
June-October 2025

Winter Island Tour

Explore the marine creatures that inhabit the tidepool on the rocky shore at Winter Island, Salem Massachusetts

Explore the marine creatures that inhabit the tidepool on the rocky shore! Salem Sound Coastwatch staff will bring buckets, nets, and ID guides and help you identify what we find. We recommend wearing sturdy shoes (no open toes) that can get wet and traverse slippery rocks. Please meet at the Winter Island rain garden (look for the SSCW flag!) and let the gatehouse staff know you’re with us. All ages welcome. Event will be held rain or shine unless there is thunder or lightning. Part of Trails & Sails.

When: 
Saturday, September 13, 2025 9:30-10:30

Blacksmithing Saturday at the Essex Company Forge

Lawrence History Center hosts a day of blacksmithing at the Essex Company Forge in Massachusetts!

Step back in time with us for a day of blacksmithing at the Essex Company forge, the company that built the city of Lawrence! Blacksmith Richard Wright will be demonstrating the craft of traditional blacksmithing methods, forging both iron and mild steel to create items for practical use in our historic courtyard. The forge was first in use in the early 1880’s when the Essex Company complex at 6 Essex Street in Lawrence was constructed.

When: 
Saturday, September 13, 2025 9:30am-1:30pm

Waterpower at the Saugus Iron Works Tour

Free Ranger guided tours at Saugus Iron Works Colonial Industrial Site in Massachusetts

How did water drive early industries in colonial Massachusetts? Join a park ranger for a special tour focused on waterpower at the Saugus Iron Works in Massachusetts. Hear the crash of the hammer and the bang of the bellows as we demonstrate a variety of waterwheels at the Iron Works. Learn how waterwheels were made historically, and how modern carpenters and preservationists repair and rebuild waterwheels.

When: 
Saturday, September 13, 2025 10am-1pm

Kite Day at Cogswell's Grant

Kite Day at Cogswell Grant is a wonderful fall afternoon event for North Shore families

Come fly a kite at Cogswell's Grant in Essex Massachusetts! Bring your own kite or build one of your own, and watch professional kite flyers from Kites Over New England. Kite-building workshops will be held with all materials included, where kids and adults can make their own kites and learn how to fly them.

When: 
Saturday, September 13, 2025 10am-4pm
Rain Date, September 14, 2025

Plumfest 2025

Plumfest is an annual celebration of music and community on Plum Island in Newburyport

PlumFest is a non-profit volunteer-run organization incorporated as a Charitable Foundation to bring local musicians, island residents and visitors together to showcase the natural beauty and artistry that make Plum Island such a special place. As an early participant in the “porch-fest” movement that is gaining popularity nation-wide, PlumFest brings our own unique flavor to the mix, with an event that is sure to please.

When: 
Saturday, September 13, 2025 12-6pm

Discover the Highest Point on the Essex Seacoast!

Take a Trails & Sails hike to the top of Powow Hill in Amesbury Massachusetts!

Come join Amesbury Trails for a guided hikeup Powow Hill, at the summit of the highest peak on the Essex County Seacoast! This narrated hike will include the historical background of the area and descriptions of the features and landscapes encountered along the hike. Enjoy exploring a variety of biomes as we climb from the edge of Lake Gardner, through wetlands, hardwood and pine forest to reach the highest point on the Essex Seacoast – Powow Hill! Views of three states and the Isles of Shoals await us as we visit Batchelder Park on the summit, established 100 years ago!

When: 
Wednesday, September 24, 2025 10-11:30am
Location: 

Lowell's Boat Shop: Boatbuilding in the New Nation

Learn about Lowell's Boat Shop in Amesbury Massachusetts on this guided Trails and Sails Tour

Step back in time with a visit to Lowell’s Boat Shop  in Amesbury Massachusetts during Trails & Sails! Established in 1793, Lowell’s was one of The New Nation’s many boat shops, and is the oldest continuously operating boat shop in the country. Simeon Lowell founded his own business after working as a shipwright in the area; he and other Lowell family shipwrights participated in the build of The Alliance, one of the first frigates built for the Revolutionary Navy.

When: 
Thursday, September 19, 2025 11am-2pm
Friday, September 20, 2025 11am-2pm

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Landmark Summer Experience at Landmark School in Beverly 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

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

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

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

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

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

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

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

Saturday, December 13

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

Breakfast with Santa

Kids will enjoy breakfast with Santa at the Hamilton Wenham Community House
Come and enjoy a continental style breakfast and get your picture taken with Santa. We will also have a letter writing station and music entertainment.
8:00 am to 12:30 pm

Middle Street Walk 2025

The lighting of the Lobster Trap Tree is part of Middle Street Walk's finale in Gloucester Massachusetts.
The Annual Middle Street Walk is a great way to experience Gloucester's Historic District and waterfront while having Holiday fun with the family.
9:00 am to 5:00 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

Boot Camp For Birth Support & Beyond

Boot Camp For Birth Support & Beyond for caregivers at Beverly Hospital in Massachusetts
Most education surrounding childbirth focuses on the person carrying the child, as it rightly should. Those in the role of supporting childbirth (spouses, significant others, couples using a surrogate, etc) should be equally as prepared for the joys and challenges in store. In this class you’ll...
9:00 am to 11:00 am

Newburyport Holiday House Tour 2025

Newburyport Holiday House Tour hosted by the Newburyport PTO Kitchen Tour
Enjoy touring private residences and unique spaces throughout Greater Newburyport, all decorated in holiday style both inside and out. Your self-guide tour will lead you through each of our homes all decked out both inside and out in holiday style reflecting the homeowner’s individual celebrations...
9:30 am to 4:00 pm

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

Middle Street Walk Gingerbread Contest 2025

Middle Street Walk Gingerbread Contest entries can take any shape.
Everybody is invited to enter the Gingerbread Contest for the Middle Street Walk in Gloucester this year! Groups and individuals are encouraged to get creative and come up with entries that can take any shape.  All entries will be judged prior to the start of the Middle Street at 10am. 
10:00 am to 3:00 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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