Trails & Sails 2025

Visit the Manchester-by-the-Sea Museum

Manchester-by-the-Seab Museum tours in Massachusetts. A Trails and Sails event.

Discover Manchester-by-the-Sea’s history, architecture & art through our exhibits, tours & collections. See our Salt Cod Fish Yard, original Singing Beach Bath House, and the exhibit “Summers by the Sea: Masconomo House Hotel & the Resort Era,” which examines Manchester-by-the-Sea’s transformation from a furniture-making mill town to an international summer-resort destination. This event is part of Trails & Sails

When: 
Wednesday-Saturday, September 13-27, 2025 11am-4pm

Northern Strand Community Path Ride

Ride the Northern Strand Path as a group starting in Lynn Massachusetts! Part of Trails & Sails

This low-stress ride will be led by Dave Read of the Border to Boston Trail Coalition. We’ll start in the Market Basket parking lot next to the trail in Lynn, go over the Saugus River and past the Rumney Marsh in Revere. Meet next to the trail at the Market Basket in Lynn. There will be two options: one to Malden line (12 miles round trip) and a bit longer to the Everett line (16 miles round trip). This is a paved trail. Part of Trails & Sails.

When: 
Sunday, September 14, 2025 10am-Noon

Historic Port of Ipswich Tour

Ipswich Museum hosts a Trails and Sails Historic Tour of the Town of Ipswich Massachusetts as a port.

Join local history buff, Scott Jewell, on a walk around the town of Ipswich and learn about the fascinating history of its former bustling port. Once a hub of maritime trade and commerce, the fate of the port was intricately tied to the rise and fall of the town’s 18th century economy, and the fortunes (and misfortunes) of many of its residents. Part of Trails & Sails.

When: 
Saturday, September 20, 2025 1-3pm

Brocklebank Museum Open House

Explore the Brocklebank Museum in Georgetown Massachusetts as part of Trails and Sails!

Visit the Brocklebank Museum, built in the late 1600s, with ties to the abolitionist movement and the famous Beecher family. tep back in time to the birth of our Nation. The Revolutionary War era in Essex County. Stop by and visit the Georgetown Historical Society in our tavern room at the Brockleback, Nelson, Beecher house.

When: 
Sunday, September 14, 2025 1-4pm
Sunday, September 21, 20025 1-4pm
Sunday, September 28, 2025 1-4pm

Overlooking the Essex River Tour

Tour Cogswell's Grant Coastal Farm in Essex Massachusetts as part of Trails & Sails

On this walking tour, explore the landscape history at Cogswell’s Grant in Essex, Massachusetts, from the presence of indigenous people through the colonial period to the present. Walk through hayfields down to the salt marsh and the Essex River, discover the rich history of the people and families who lived and farmed here, and learn how coastal farming has evolved over the centuries. Part of Trails & Sails. Reservations Required

When: 
Saturday, September 27, 2025 11am-12:30pm

Make a Car or Boat Craft at APL

Kids are invited to come the Amesbury Public Library to a Car or Boat to take home!

Bring the family to create a 3D car or an origami boat in a bottle. All supplies will be outside and enjoyed during the Annual Car Show in downtown Amesbury in the quiet of the Library programming area. Build, decorate, and enjoy some books about transportation! After you’re done with your craft, be sure to check out the Carriagetown Car Show!

When: 
Saturday, September 27, 2025

Salisbury Days: Touch a Truck

Kids (and adults) can get up close and personal with all kinds of trucks in Salisbury Massachusetts
Salisbury Days are hosting a Touch-A-Truck event! Get up close and personal with all the trucks/unique vehicles you see on the road. Meet the people who drive them and learn about what they do! If you have a truck or any unique vehicle you would like to showcase in our event, feel free to message us to get on the participant list!
When: 
Sunday, September 21, 2025 Noon-4pm

Ride the Rail Trail to New Hampshire

Bike the Rail Trail from the Merrimack river in Salisbury Massachusetts to the New Hampshire border.

Join us on a scenic bike ride starting at the Graf Rink lot on Low St. in Newburyport. We’ll go along the Clipper City Trail and it’s impressive trail art. We will then go over the Merrimac River to Salisbury, past salt marshes as we make our way to the NH border. Along the way, David Read will share how it fits into the greater Border to Boston Trail and the East Coast Greenway! We will meet next to the trail at the Graf Rink parking area on Low St. in Newburyport. The round trip is 10 miles on an all-paved surface.

When: 
Sunday, September 28, 2025 10am - Noon

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Brookwood School Summer Program for kids Pre-K through 9 in Manchester 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

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

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

Witch City 5k

Witch City 5k - a YMCA 5k costume run in downtown Salem Massachusetts!
Run through the haunted streets of Salem with ghouls, ghosts and goblins in this community favorite 5K event that takes place during the most fun time in Salem...October’s Haunted Happenings!
9:00 am to 12:00 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

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

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

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

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

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

Haunted Biz Baz Street Fair

The Biz Baz Street Fair in Salem Massachusetts hosts dozens of Chamber members and unique vendors selling handmade art, crafts, gifts, apparel, and more.
Come visit the Biz Baz Street Fair to see over 80 vendors and enjoy the historic Salem Common. Vendor sales include handmade jewelry, art, apparel, crafts, Halloween decor and so much more!
10:00 am to 8:00 pm

Topsfield Fair

Topsfield Fair is one of the longest running annual fairs in the United States
The Topsfield Fair is a perennial favorite for us.  We're not the biggest fans of the midway, although it is always worth a walkthrough and a ride or two.  We love fruits and vegetables, and are always on the lookout for the winning 'biggest pumpkin'.  Another favorite is checking out the pigs and...
10:00 am to 10:00 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

Haunted Happenings Marketplace

The Haunted Happenings Marketplace runs Thursdays-Sundays during October in Salem Massachusetts
The Haunted Happenings Merchant Marketplace is coming this October! Get ready for a one-of-a-kind shopping extravaganza throughout Historic (and some say haunted) Downtown Salem!
10:00 am to 6:00 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

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

Newburyport Chocolate Tour

The Newburyport Chocolate Tour is a chance for chocolate lover to experience the best treats of Newburyport Massachusetts!
A sweet stroll with a purpose— The Chocolate Tour is a community-driven tasting experience through the charming streets of downtown Amesbury and Newburyport. Local shops serve up chocolate delights while you explore, shop, and support amazing causes. Even sweeter? Every ticket helps fund local...
12:00 pm to 4:00 pm

Georgia Made This: Scavenger Coin Hunt

Georgia Wrenn was born and is being raised in the Witch City of Salem, Massachusetts, where Halloween is celebrated 365 days a year.
Georgia's seventh annual Salem Gold Coin Hunt returns this October, courtesy of the Peabody Essex Museum! Each Saturday and Sunday throughout October, Georgia will release special clues at 12 noon through her Instagram page and the PEM's Instagram story. Those clues will help coin hunters narrow...
12:00 pm to 7:00 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

Halloween on the Hill

The Trustees host a celebration of Autumn and Halloween at Long Hill Sedgewick Gardens in Beverly Massachusetts
The Trustees of Reservations invite you to tour the gardens at Long Hill Gardens in Beverly, Massachusetts to celebrate Autumn and Halloween! Long Hill is excited to bring back our annual Halloween on the Hill event! Come explore our beautiful property as we transform the Long Hill gardens into a...
5:00 pm to 8:30 pm

Sunday, October 5

Halloween on the Hill

The Trustees host a celebration of Autumn and Halloween at Long Hill Sedgewick Gardens in Beverly Massachusetts
The Trustees of Reservations invite you to tour the gardens at Long Hill Gardens in Beverly, Massachusetts to celebrate Autumn and Halloween! Long Hill is excited to bring back our annual Halloween on the Hill event! Come explore our beautiful property as we transform the Long Hill gardens into a...
5:00 pm to 8:30 pm

Monday, October 6

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

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

Topsfield Fair

Topsfield Fair is one of the longest running annual fairs in the United States
The Topsfield Fair is a perennial favorite for us.  We're not the biggest fans of the midway, although it is always worth a walkthrough and a ride or two.  We love fruits and vegetables, and are always on the lookout for the winning 'biggest pumpkin'.  Another favorite is checking out the pigs and...
10:00 am to 10:00 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

Beverly Farmers' Market

Get fresh local produce at the Beverly Farmers Market in downtown Beverly Massac
The Beverly Farmers’ Market supports local agriculture while making healthy food available to all members of the Beverly community at affordable prices; the market promotes sustainable living practices and fosters community connections through our vendors, free activities and events. The market...
Where: Odell Park
3:00 pm to 7:00 pm

Tuesday, October 7

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
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