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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

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 celebration of autumn and the Halloween season. As always, there are a few new surprises and of course many more pumpkins this year. Follow our seasonal-themed trail that will feature over 1,500 jack-o'-lanterns, hundreds of mums, elaborate Halloween decorations, light displays, music, and more. This is the perfect Halloween event for the whole family!

When: 
Wednesdays-Sundays, October 3-30, 2025 5:30-8:30pm

GNOCA 5K Run/Walk

GNOCA's 5K Run/Walk in Honor of Jackie Poor & Paula Holm is a 5k Run or Family Friendly Stroll through Scenic Newburyport starting & ending at Michael's Harborside. Tee Shirts will be given to the First 100 Registrants. All participating runners will be assigned numbers and timed. Great Prizes for Age Category Winners!

When: 
Sunday, September 28, 2025 8AM-1PM

Choate Island Day

Choate Island Day with the Trustees of Reservations in Ipswich Massachusetts

Spend a day with the Trustees of Reservations in celebration of Choate Island – the crown jewel of the Crane Wildlife Refuge. Here deer and foxes roam through fields that once housed herds of sheep, and osprey fly over breathtaking views of Essex Bay. The island was first home to indigenous farmers and fishers, then to generations of the Choate family, and was later a retreat for Cornelius and Miné Crane, who loved the place so much they decided to be buried at the summit.

When: 
Saturday, September 27, 2025 10AM-3PM
Last Admission at 1pm

A Spiritual Quest Weekend at Hilldale Cemetery

Hilldale Cemetary in Haverhill Massachusetts is one of the North Shore's most active paranormal spots!

Do you believe in Ghosts? If you do then join the Essex County Ghost Project and Witches Wonder fort a spooktacular evening of haunts and fun . The gates open at 6:30 pm and hunt starts at 7pm . We are exploring one of New England’s most Haunted historical sites . There have been reports of full and partial body apparitions, voices , shadow figures and more . So pack up your cameras , pendulums, digital recorders and other paranormal equipment for a night of paranormal history and intrigue .

When: 
Saturdays, September 13, 20 & 27, 2025 7-9:30pm
Fridays, September 19 & 26, 2025 7-9:30pm

Fairy House Festival at Veasey Park

Fairy House Festival at Veasey Park Groveland Massachusetts Trails and Sails 2023

Walk the trails to see the handcrafted houses at this year’s enchanted Fairy House Festival. Cast your People’s Choice Award vote for your favorite Fairy House. Stay awhile for magical fun, arts and crafts, food, raffles, live music, and more. Rain or shine. Anyone is welcome to submit a house. Donations collected at the Festival are reinvested back into the Park. Part of Trails & Sails

When: 
Saturday, September 20, 2025 10am – 4pm
Sunday, September 21, 2025 10am – 4pm
Location: 

Farm-Forest-Ice Cream Hike

Join this Trails and Sails Hike through the woods in Ipswich for an ice cream treat! A Sails & Trails event.

A group hike from Marini Farm through the forest to White Farms for an optional ice cream. Don’t miss this great opportunity to explore the farm, forest, and nature of Ipswich. The group will meet on Linebrook Road in Ipswich. Bike entrance to Willowdale State Forest just west of Marini Farm. Look for the Event sign. Bring water, sunscreen, bug spray and good hiking shoes. this is a Trails & Sails Event.

When: 
Saturday, September 13, 2025 11am-2:15pm
Location: 

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Appleton Farms in Ipswich Massachusetts offers farm-based Summer Programs for kids ages 5-15

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

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

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

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

Gloucester Gratis Days at Hammond Castle

Bring your kids to the Hammond Castle Museum in Gloucester Massachusetts during April Vacation
In keeping with John Hays Hammond, Jr's original vision for his seaside castle-home to serve as a museum offering the Gloucester community access to ancient works of architectural art, Hammond Castle Museum will offer Gloucester residents free, self-guided tours each Tuesday throughout the regular...
10:00 am to 4:00 pm

Wednesday, October 1

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

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

Mini Movers at North Shore Children's Museum

Things to do for children in Peabody MA
Mini Movers is an engaging dance and movement class for young children at the North Shore Children's Museum. Led by experienced instructors, the program introduces young children to the world of dance in a safe and nurturing environment.
10:00 am to 11:00 am

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

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

The Backyard Growcery

Join Backyard Growers at Burnham's Field in Gloucester Massachusetts for a weekly Farmer's Market
Stop by Gloucester’s new weekly farmers market, the Backyard Growcery, managed by Backyard Growers. The Backyard Growcery is located at Burnham's Field, an urban park near Gloucester’s thriving waterfront, and features small-scale North Shore farmers, bakers, a seafood vendor, an artisanal pizza...
2:30 pm to 6:30 pm
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