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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

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

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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Shore School in Beverly Massachusetts offers a host of Summer programs for kids aged 5-12

Boston Bruins Annual Pajama Drive

Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.
The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses...
7:00 am to 9:00 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

CraneOutdoors: The Castle Hill Hike

CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
10:00 am to 12:00 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

Wednesday, March 18

Stargazing at Mendel Observatory

Mendel Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night
The Observatory, with the support of volunteers from the North Shore Amateur Astronomy Club, hosts public stargazing every Wednesday night (weather permitting) starting at dusk or 7:30 pm, whichever is later.  When special astronomical events of interest occur (total lunar eclipses, etc.) the Obs
7:00 pm

Thursday, March 19

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

Friday, March 20

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

Saturday, March 21

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

CraneOutdoors: The Castle Hill Hike

CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
10:00 am to 12:00 pm

Low-Sensory Play at North Shore Children's Museum

Low-Sensory Play at NorthShore Children's Museum in Peabody Massachusetts
Join us for a low-sensory play session. For some children, visiting places like NSCM can be over-stimulating. This special play session will have reduced noise, crowds, and stimulation. While medical diagnosis is not required, we encourage that these limited tickets be used for families with a...
2:00 pm to 4:00 pm

Sunday, March 22

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

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 3:30 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

Symphony by the Sea | Winter Dreams

Symphony by the Sea: Winter Dreams at the Cabot Theater in Beverly Massachusetts!
Symphony by the Sea performs a special Winter Concert inspired by Slavic fairytales and the beauty of the Russian landscape, our program explores the rich synthesis of Western musical tradition and Russian folk melodies. Tchaikovsky’s energetic and tuneful Serenade, Arensky’s touching tribute to...
Where: The Cabot
3:00 pm
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