All Ages

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

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! The Biz Baz will be in the Salem Common and you can shop on Saturday, October 4, from 10AM-6PM, and Sunday, October 5, from 10AM-6PM. This event brings thousands of visitors, so you do not want to miss out! Hosted by the Salem Chamber of Commerce.

When: 
Saturday, October 5, 2024 10am-6pm
Sunday, October 6, 2024 10am-6pm
Location: 

Jan's Pitch for Breast Cancer and the Arts

Come to a vintage baseball match that raises funds for breast cancer research at Spencer Peirce Little Farm in Newbury

Join Spencer-Peirce-Little Farm and the Essex Base Ball Association for a day of vintage base ball as we celebrate the 20th season of this partnership! The four teams of Essex Base Ball, the Newburyport Clamdiggers, Lowell Base Ball Club, Portsmouth Rockingham's, and the Lynn Live Oaks, play using 1864 rules. At these fun, historically accurate games, gloves are not allowed, players pitch underhand, and a ball bounced once and caught is an out. Bring a picnic or partake in beer and hot dogs from our friends at Ipswich Ale!

When: 
Sunday, October 5, 2025 11am-3pm

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 nonprofits—so while you indulge, you're also giving back to the community.

When: 
Saturday, October 4, 2025 5-7pm

Walk Against Domestic Violence

Jeanne Geiger Annual Walk Against Domestic Violence in Newburyport Massachusetts

The Walk Against Domestic Violence is hosted by Jeanne Geiger Crisis Center in Newburyport, Massachusetts. We walk because it could be your best friend, your younger sister, the man who works in the office next to you, your child's best friend, or the teenage girl who works in the local coffee shop. We walk because domestic violence doesn't have a face, because it could happen to anyone, at any time. Walk with us as we advocate for change and raise awareness for domestic violence.

When: 
Sunday, October 5, 2025 9-12pm

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

Paddle Around Historic Rockport Harbor

Paddle around Rockport Massachusetts Harbor for FREE as part of Trails and Sails

Come join North Shore Adventures and Outdoor Center for some fun on the water! No experience necessary. Depart from our private beach in one of our safe, stable kayaks or paddle boards and paddle around the historic Rockport Harbor for 30 mins. See lobster boats, Motif #1, the Rockport Break water, and the gorgeous Head Lands property. This is your only chance to kayak/SUP for free!! Come join us any day Sept. 13-28 at 10:30am.

When: 
Daily, September 13-28, 2025 10:30-11am

Climb Up Gloucester City Hall Tower

Take a Free tour of Gloucester Massachusetts City Hall's renovated tower as part of Trails and Sails 2024!

Experience the WOW factor when you climb up Gloucester’s City Hall clock and bell tower and emerge at the bell level. Views, weather permitting, are awesome. Members of Gloucester’s City Hall Restoration Commission will be on hand to inform you of the history of this architecturally significant building that had graced Gloucester’s skyline for more than 150 years. Please note that while the tower is not handicapped accessible the WPA Murals in City Hall are accessible and are one, if not, the best collection of WPA murals in the Commonwealth.

When: 
Saturday, September 27, 2025 Noon-3pm

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

Maritime Adventure Days

Maritime Adventure Free Days at Custom House Maritime Museum Newburyport Massachusetts

Maritime Adventure Free Days offers families and kids a unique opportunity to explore maritime history through interactive activities, guided tours, and hands-on workshops. A day of fun and discovery at the Custom House Maritime Museum for the family. These free Saturday events include experiencing a traditional Wampanoag dugout canoe being made by a team of craftsmen. Part of Trails & Sails

When: 
Saturday, September 13, 2025 9am-1pm
Saturday, September 20, 2025 9am-1pm
Saturday, September 27, 2025 9am-1pm

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

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

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

Kimball Farm Corn Maze

Kimball Farm corn maze in Haverhill Massachusetts
At the Kimball Farm Corn Maze all are welcome to come and enjoy the challenge of finding your way through the winding corn field maze. Our originally designed CORN MAZE  is full of Crazy angles and is sure to be a fun challenge. Have no fear, there will be clues along the way.  Be daring and try...
10:00 am to 9:00 pm

Ipswich Illumination

Come to Ipswich Massachusetts as points along the Ipswich River are illuminated!
The Town of Ipswich, Massachusetts, proudly presents 2025 Ipswich Illumination. This year we are celebrating harvest, hearth, & home, and our maritime history, heritage & culture.
11:00 am to 9:30 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

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

Danvers Halloween Happenings

Hallween Happenings at Endicott Park in Danvers Massachusetts
The Town of Danvers hosts a non-scary, family-friendly Halloween event designed for children of all ages! The event will feature arts & crafts, children's games, a hay ride through the park, and treats and entertainment by the campfire! ALL members of your family who are attending must be...
4:30 pm to 8:00 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 26

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

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

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

Kimball Farm Corn Maze

Kimball Farm corn maze in Haverhill Massachusetts
At the Kimball Farm Corn Maze all are welcome to come and enjoy the challenge of finding your way through the winding corn field maze. Our originally designed CORN MAZE  is full of Crazy angles and is sure to be a fun challenge. Have no fear, there will be clues along the way.  Be daring and try...
10:00 am to 9:00 pm

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
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