Outdoor Activity

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

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

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: 

COASTSWEEP Cleanup | Short Beach Nahant

CoastSweep shoreline beach cleanup at Short Beach in Nahant, Massachusetts!

As part of COASTSWEEP Beach Cleanup, volunteers are encouraged to come to Short Beach, Nahant (located opposite the corner of Nahant Road and Castle Road) to help in the statewide effort to keep our coastline clean along the shore in Lynn and Nahant Massachusetts. Special two hour permits will be given out at our tables at the Lowlands Parking Lot on Ward Road to avoid parking tickets.  Coordinator: Vi Patek

When: 
Sunday, September 28, 2025 11am

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

Ride the Coastal Trails Network

Take a ride with the Coastal Trails Coalition through Amesbury, Newburyport and Salisbury Massachusetts!

Join Coastal Trails Coalition on a bike ride on the Coastal Trails in Newburyport, Amesbury and Salisbury on a combination of quiet streets and paved and stone dust trails, with two crossings of the Merrimack River beside US 1 and I-95. We’ll cycle through woods, salt marsh, neighborhoods, and Newburyport’s historic downtown. The total length is 12 miles on mostly flat terrain, with short climbs on the bridges over the river. If participants wish, the route can be extended to look at other parts of the system.

When: 
Sunday, September 14, 2025 10am- Noon
Location: 

Historic Port of Ipswich Tour

Ipswich Museum hosts a Trails and Sails Historic Tour of the Town of Ipswich Massachusetts as a port.

Join local history buff, Scott Jewell, on a walk around the town of Ipswich and learn about the fascinating history of its former bustling port. Once a hub of maritime trade and commerce, the fate of the port was intricately tied to the rise and fall of the town’s 18th century economy, and the fortunes (and misfortunes) of many of its residents. Part of Trails & Sails.

When: 
Saturday, September 20, 2025 1-3pm

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

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

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
10:00 am to 8:00 pm

Tree Jubilee at Marini Farm

The Tree Jubilee hosted by Marini Farm in Ipswich Massachusetts is a fun and unique charity event!
Come to Marini Farm for the Tree Jubilee fundraiser to benefit The Ipswich Humane Group.  Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and...
10:00 am

SeaFestival of Trees in Salisbury

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 8:00 pm

SeaFestival of Trees in Salisbury | Saturdays

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 8:00 pm

Salem Holiday Tree Lighting

Come to the Holiday Tree Lighting in Salem to kick off the holiday season!
Join Salem Main Streets and the City of Salem as we combine two of our most beloved annual traditions – Greet Santa at the Hawthorne Hotel and the lighting of Salem’s Holiday Tree – into one evening. Santa Claus will arrive at the top of the Hawthorne Hotel (18 Washington Square W) promptly at 6:00...
5:45 pm to 6:30 pm

Greet Santa at the Hawthorne Hotel

Salem Main Streets, SalemMainStreets.org, Visit Salem MA for the holidays
Join Salem Main Streets and the City of Salem as we celebrate two of our most beloved annual traditions – Santa’s Arrival and the lighting of Salem’s Holiday Tree – all in one evening. Santa Claus will arrive at the top of the Hawthorne Hotel (18 Washington Square W) promptly at 6:00 p.m. on Friday...
5:45 pm to 8:00 pm

Beverly Tree Lighting

Beverly Massachusetts holiday tree lighting on the Common is a favorite community event!
Come to the Beverly Tree Lighting!  Gather with your neighbors and enjoy cocoa, cookies, music and Santa, as we light the town Holiday Tree!
7:00 pm

Saturday, November 29

Cape Ann Symphony Holiday Pops

Cape Ann Symphony Holiday Pops Concert in Ipswich and Manchester Massachsusetts
Celebrate the Holidays on Thanksgiving weekend with the Cape Ann Symphony conducted by Yoichi Udagawa. The annual Holiday Pops is a musical celebration of the season.
2:00 pm

Sunday, November 30

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

Tree Jubilee at Marini Farm

The Tree Jubilee hosted by Marini Farm in Ipswich Massachusetts is a fun and unique charity event!
Come to Marini Farm for the Tree Jubilee fundraiser to benefit The Ipswich Humane Group.  Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and...
10:00 am

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
10:00 am to 8:00 pm

SeaFestival of Trees | Sundays

Browse our maze of festively decorated trees and enjoy a little holiday sparkleat the SeaFestival of Trees in Salisbury Massachusetts
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 5:00 pm

SeaFestival of Trees | Elf Day

Experience the joy and excitement of Salisbury’s most popular holiday tradition with glittering trees, Elves, Santa, Candy Canes and more!
Don’t be a cotton headed ninny muggins! Spread some Christmas cheer with Buddy the Elf, have a snowball fight, make paper snowflakes, test toys at Santa’s Workshop and more! FREE with admission.
12:00 pm to 2:00 pm

CraneOutdoors: Castle Neck Hike in the Dunes

Hiking the Dunes at the Crane Wildlife refuge with the Trustees of Reservations.
While just about everybody on the North Shore has probably been to Crane Beach, the dunes of Castle Neck are a much less explored world unto themselves. Offering one of the most accessible dune ecosystems north of Cape Cod, Castle Neck has over six miles of trails, traversing the dunes, maritime...
1:00 pm to 3:30 pm
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