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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 14-29, 2024

Landmark 5k Road Race and Kids Fun Run

Landmark School's annual 5K Road Race is a family fun event that helps support the mission of Landmark School.

Landmark School's 5K Road Race and Kids 1K Fun Run are part of their Homecoming & Fall Festival. It is one of the largest events of the academic year, bringing together students, parents, alumni, faculty, friends, and members of the broader North Shore community. This event is also part of the Landmark Cares fundraiser, which helps students who have dyslexia reach their full potential.

When: 
Saturday, September 21, 2024 10:30am-Noon
Location: 

Powow Scenic Vista Hike

Take a Trails & Sails hike to the top of Powow Hill in Amesbury Massachusetts!

Come join the Lake Gardener Improvement Association for a guided up Powow Hill. We will hike to the top of Powow Hill, the highest point on the Essex County seacoast! Hike through hundreds of acres of unspoiled greenspace to reach the summit vista, from which you can see three states and the Atlantic! The approximately hour-long hike will bring you from the beach at Lake Gardner to the summit. And the summit is within easy walking distance of the restaurants, brewpubs, and shops of downtown Amesbury!

When: 
Saturday, September 22, 2024 2-3:30pm
Location: 

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 22, 2024 8AM-1PM

Choate Island Day

The annual Choate Island Day celebration hosted by The Trustees at The Crane Estate is coming up on Saturday, September 28th! With a ticket to this family-friendly event, you can access Choate Island, the crown jewel of the Crane Wildlife Refuge located behind Crane Beach in Essex Bay. Hop on the bus at Crane Beach, and then take the Essex River Cruises riverboat over to the island. Enjoy guided or self-guided tours allow you to explore the island and tour three historic buildings, with a kid's scavenger hunt, light refreshments, and history & wildlife stations and talks along the way.

When: 
Saturday, September 28, 2024 10AM-3PM
Last Admission at 1pm

Useful Plants of Pioneer Village – Food, Medicine & More

Learn about colonial medicine at Pioneer Village in Salem Massachusetts

An amazing number of the plants at Pioneer Village are nutritious food, or good medicine, and/or useful in other ways. Some are native and were already here when the settlers came, others were introduced. In this fun and informative walk you will learn about these wonderful plants and some of their uses, whether they are wild and weedy or cultivated and tame. Appreciating the useful plants around us helps us to treat plants and the environment with care and respect, so they are here for future generations. You will leave with new-found awe for our plant neighbors and the many gifts they offer us!

When: 
Sunday, September 29, 2024 2-3pm
Location: 

Hike to Bootleggers Field

Join the park interpreter for a for a hike to Bootleggers Field at Madslay State Park in Newburyport, Massachusetts For ages 8 & up.

Join the park interpreter for a moderate walk, but longer hike to apark location rarely visited! Join the park interpreter on a 3 mile (round trip) hike to the northeast section of the park, known as Bootleggers Field. We’ll explore some of the mysteries of that area plus enjoy the river view, come and experience this journey! The trails are mainly flat with some sloping terrain, a walking stick is recommended. For ages 8 years & up.

When: 
Saturday, September 28, 2024 1-3pm

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Appleton Farms offers great farm-based Vacation Week Programs for kids ages 5-11

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

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

Maudslay in Bloom Self-Guided Walk

 Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
7:00 am to 7:00 pm

Crane Outdoors: Kayak Adventure on the Castle Neck River

Take a guided kayak paddle adventure on the Castle Neck River with the Trustees of Reservations!
One of the best was to enjoy the natural beauty of the Massachusetts North Shore is kayaking the placid waters of the Great Marsh—the largest continuous stretch of salt marsh in New England, extending from Cape Ann to New Hampshire. The Castle Neck peninsula on the Crane Estate is a vast barrier...
9:00 am to 5:00 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

Newburyport Spring Festival 2025

Celebrate the onset of Spring in beatuiful downtown Newburyport Massachusetts
The Newburyport Chamber of Commerce invites you to welcome Spring's arrival to Newburyport at the 2025 Spring Fest!
10:00 am to 4:00 pm

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 4:00 pm

Long Hill Garden Tours

Tour the Gardens at the Trustees of Reservations Long Hill Gardens in Beverly, Massachusetts!
The Trustees of Reservations invite you to join our expert guides for a tour around Long Hill’s stunning Sedgwick Gardens and learn more about the special plants. Visit Long Hill’s breathtaking gardens and stately historic house for a guided tour. Enjoy the rich history of this grand country estate...
11:00 am to 12:00 pm

CraneOutdoors: Choate Island Kayak and Hiking Adventure

Take a guided kayak paddle and hike to Choate Island with the Trustees of Reservations!
Join The Trustees of Reservations for a paddle and a hike – what better way to spend an afternoon? Kayaking the pristine, sheltered waters of the Essex River Basin offers one of the top on-the-water experiences to be had in Northeast. Add to that a hike on the area’s largest island and you have the...
1:00 pm to 4:30 pm

TitO presents Petrushka & the Caterpillar

Theater in the Open presents Petrushka and the Catapillar at Maudslay State Park in Newburyport Massachusetts
What happens when your favorite stories need a new ending? Everyone's favorite clown upends iconic fables and fairytales in our signature storytelling style – with tons of imagination, humor, and heart. Join Petrushka and the gang as they retell old stories for our times!
2:00 pm to 4:30 pm

Nice n' Easy Hike at Maudslay State Park

Take a nice n' easy stroll at Bradley Palmer State Park with your family!
Take a nice n' easy stroll at Bradley Palmer State Park with your family! Join the Park Interpreter for an easy hike along the Carriage Road or Accessible Trail. Points of interest will be highlighted. The walk will be fully accessible to strollers and wheelchairs. Best for ages pre-K and up.
2:00 pm

Sunday, June 1

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 4:00 pm

CoastalExplorer: Shoreline & Shipwreck Scholars

Families learn about shipwrecks at Castle Hill and Crane Beach in Ipswich Massachusetts
Coastal exploration with a side of shipwreck! Participants will be guided on a Castle Hill hike to Steep Hill Beach, where we will explore the beach and discover treasures washed up by the waves. Piece together clues to learn what is living under the sand and below the water line. We will use field...
10:00 am to 12:00 pm

Vintage Base Ball Opening Day

Come see how baseball used to be played at Spencer Pierce Little Farm. Photo: Matthew Muise Photography
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...
11:00 am to 3:30 pm

Long Hill Garden Tours

Tour the Gardens at the Trustees of Reservations Long Hill Gardens in Beverly, Massachusetts!
The Trustees of Reservations invite you to join our expert guides for a tour around Long Hill’s stunning Sedgwick Gardens and learn more about the special plants. Visit Long Hill’s breathtaking gardens and stately historic house for a guided tour. Enjoy the rich history of this grand country estate...
11:00 am to 12:00 pm

CraneOutdoors: Choate Island Kayak and Hiking Adventure

Take a guided kayak paddle and hike to Choate Island with the Trustees of Reservations!
Join The Trustees of Reservations for a paddle and a hike – what better way to spend an afternoon? Kayaking the pristine, sheltered waters of the Essex River Basin offers one of the top on-the-water experiences to be had in Northeast. Add to that a hike on the area’s largest island and you have the...
1:00 pm to 4:30 pm

Tri-town Pride Parade

Tri-Town Pride Parade ends at the Town Common in Topsfield Massachusetts
The Tri-Town Pride Parade is an annual celebration of love, diversity, and inclusivity in our community, encompassing Boxford, Middleton, Topsfield, and surrounding towns in Massachusetts. Sunday, June 1st at 1:00 PM the parade will wind its way through the charming downtown area of Topsfield,...
1:00 pm

Pajama Story Time at Manchester Public Library

Kids are invited to the pajama time book reading at the Public Library in Manchester by the Sea Massachusetts.
Join Miss Audrey for a cozy pajama storytime and craft the first Thursday of every month from 6-7. This program is for kids ages 4 and up and their families. 
6:00 pm to 7:00 pm

Monday, June 2

Maudslay in Bloom Self-Guided Walk

 Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
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

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 4:00 pm
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