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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

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

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: 

Nature’s Myth and Folklore Storytelling Series

Learn about colonial medicine at Pioneer Village in Salem Massachusetts

Come to Pioneer Village for a craft and storytelling event that shares tales of natural folklore and wild wisdom from around the world. These stories inspire an appreciation for different cultures as well as encourage engagement with the natural environment.

When: 
Saturday, September 27, 2025 3:30-4:30pm
Location: 

History Walk at Maudslay State Park

Kids will learn about the history of Maudslay State Park through storytelling by the park interpretor

Join Maudslay State Park interpreter on a tour of the former Moseley Family estate. There are so many stories about the Moseley’s and their beautiful former estate. Join the park interpreter on a guided tour to view the site of the family mansion and their daughter Helen’s house, both areas are picturesque and have open vistas overlooking the Merrimack River. During the walk Moseley Family stories and archival photos of their estate will be shared too.

When: 
Saturday, September 20, 2025 2-3pm

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

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Art Academy Summer Program at Montserrat College of Art in Beverly MA

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Run for the Fund 5k and Family Walk

Run for the Fund 5k fundraiser charity race in Marblehead! Benfitting Marblehead Dollars for Scholars
The Run for the Fund supports the Marblehead Dollars for Scholars®, a charitable foundation that provides financial aid solely based on financial
9:00 am

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

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
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