Boat

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

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

Open Boarding on the Hannah (AKA the Fame)

Board Schooner Fame at the waterfront in Marblehead Massachusetts as part of trails and sails!

The Hannah, the first of several schooners commissioned by General George Washington, began her career as an armed cruiser in September 1775. To commemorate that important part of Marblehead’s history, the Fame – similar in size and appearance to the Hannah (aka Schooner Fame)– will be docked at Marblehead’s Town Landing from 9:00 am to 10:15 am on Saturday, September 20th, and Sunday, September 21st.

When: 
Saturday, September 20, 2025 9-10:15am
Sunday, September 21, 2025 9-10:15am

Make a Car or Boat Craft at APL

Kids are invited to come the Amesbury Public Library to a Car or Boat to take home!

Bring the family to create a 3D car or an origami boat in a bottle. All supplies will be outside and enjoyed during the Annual Car Show in downtown Amesbury in the quiet of the Library programming area. Build, decorate, and enjoy some books about transportation! After you’re done with your craft, be sure to check out the Carriagetown Car Show!

When: 
Saturday, September 27, 2025

Boat Tour to Misery Island

Journey on Essex Heritage’s landing craft Naumkeag to Great Misery Island in Salem Sound Massachusetts

Journey on Essex Heritage’s landing craft Naumkeag to Great Misery Island in Salem Sound. Along the way, hear stories about the rich history of the harbor and how the Misery Islands acquired their unique name. When you arrive, you’ll have 2 hours to explore the trails, open meadows, rocky shoreline, and hidden coves on the island. The Misery Islands are managed by The Trustees. Time allotted is about 3 hours round-trip (30-minute trip to and from the islands, and 2 hours on Great Misery Island). More information about the islands as well as a trail map can be found HERE

When: 
Saturdays through September 13, 2025 11am or 12:30pm

Kids Sail Free on the Schooner Lannon

Kids ride free on the 10:30am an Noon Saturday Cruise on the Schooner Lannon through Summer

Schooner Thomas E. Lannon is a fixture on the Gloucester Harbor vista throughout the day in the warm months, but to really experience the Lannon, you need to come aboard and go for a cruise!  Sail and see lighthouses, castles, scenic beaches, and magnificent waterfront homes.

When: 
Saturdays through July and August 2025, 10:30am or Noon

Essex Heritage Boat Tours to Bakers Island Lighthouse - Salem

Boat and Light Station Tour Bakers Island Tour out of Salem Massachusetts

Climb aboard Naumkeag, Essex Heritage’s landing craft for a trip to Bakers Island Light Station. Enjoy a 30-minute cruise from Salem past rugged coastline, harbor islands, and five lighthouses to Bakers Island. The light station is a 10-acre property that has been in use aiding in maritime navigation for almost 250 years. The site features an 1820 light tower, two keepers houses, and historic trails. During your visit you will have the chance to explore the natural landscape, learn about the history of the light station, and relax on the island setting.

When: 
Sundays through September 14, 2025 1-3:30pm

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 makings of an epic adventure. This combined outdoor trip in the Crane Wildlife Refuge—home to myriad birds and mammals including egrets, herons, deer, and coyote—offers an opportunity to fully experience all this beautiful area has to offer.

When: 
Sunday & Monday May 25 & 26, 2025
Saturdays, May 31 - August 30, 2025 1-4:30pm
Sundays, June 15 - August 31, 2025 1-4:30pm
No session: June 14, 21 & 28, July 13 & 27, August 16

Model Boat Building and Regatta

Kids can build a model boat and race it in a regatta on Redd's Pond in Marblehead

BRING THE KIDS - BRING YOUR FOLKS - BUILD & SAIL YOUR VERY OWN BOAT! This popular event begins with a workshop where participants construct model boats from provided kits at the Lee Mansion Gardens and ends with a competitive regatta at Redd's Pond. These small treasures are more than just toys—they really sail. This fun and educational activity is perfect for the whole family.

When: 
Thursday, July 3, 2025 10am-4pm

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Brookwood School Summer Program for kids Pre-K through 9 in Manchester 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

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

Discover Saturdays at Cape Ann Museum

Discover Saturdays for Families at Cape Ann Museum in Gloucester Massachusetts
Enjoy a FREE guided activity (ages 4+) in the gallery. Learn about Cape Ann’s Granite Industry, try a fun art making activity, and join in gallery tour designed for kids and their caregivers, led by a CAM Educator. Afterwards grab a scavenger hunt to explore the property and enjoy the lawn.
10:00 am to 12:00 pm

Maple Sugaring at Breakheart Reservation

Come to Breakheart Reservation Saugus Massachusetts to learn about maple sugaring - the process of making syrup..
Come to Breakheart Reservation for this FUN annual event! Experience the process of maple sugarin’ from tapping a tree to sampling real maple syrup.
10:00 am to 2:00 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

2nd Saturday at Lynn Museum

Lynn Museum in Massachusetts offers free admission on the second Saturday of each month.
Come to the Lynn Museum and Historical Society for FREE family fun. Join us on the second and fourth Saturday of each month for FREE admission to the Museum from 10 a.m. – 2 p.m.! You can view our latest exhibitions, purchase Lynn-themed goods in our shop, check out books in our free library, and...
10:00 am to 2:00 pm

Maple Sugaring Saturday at IRWS

Sugaring Off tours are a fun and tasty way to learn about maple sugaring at IRWS
Experience the age-old tradition of maple sugaring at Ipswich River Wildlife Sanctuary! The warm days of late winter awaken the flow of sap in the maples resulting in sweet-smelling, billowing clouds of steam rising from the sugarhouse. On a naturalist-guided walk, learn how to identify a sugar...
10:30 am to 3:30 pm

Sunday, March 15

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

Wonderful Winter Birding

Beginning winter birding is held on the 3rd Sunday of each Winter month at Halibut Point State Park in Rockport Massachusetts
Halibut Point State Park, along the Atlantic migratory path, is an excellent locale for winter birding species you rarely see anywhere else.Winter brings birds and ducks from frozen ponds up north to our seashore. See Harlequin ducks and loons among the winter visitors at this rocky coastal water’s...
8:00 am to 10:00 am

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

Boston Children's Chorus at Shalin Liu

Boston Children's Chorus will perform live at the Shalin Liu Center for the Performing Arts in Rockport Massachusetts
This season, Boston Children’s Chorus honors the unheralded voices who shaped history from the shadows. Their courage fueled the fires of justice. Through powerful music and storytelling, our singers shine a light on local and national activists, who stood for dignity, equality, and hope. Their...
3:00 pm

Monday, March 16

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

Tuesday, March 17

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

Wednesday, March 18

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

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
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