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

Owl Prowl Hike at Appleton Farms

Learn all about owls at Appleton Farms in Ipswich Massachusetts for kids older than 12
Join us for a very special evening hike to see the owls who might be out and about in the dark winter woods and fields of Appleton Farms. This hike will take place along the trails of Appleton, known to have multiple species of owls. Before our hike, you’ll learn about wintertime nocturnal animals...
4:15 pm to 5:45 pm

Friday, January 23

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

Winter Family Field Trip: Terrific Animal Tracking

Families will learn about identifying animal tracks at Joppa Flats Education Center in Newburyport Massachusetts!
Mammals such as squirrels, rabbits and deer leave many signs that they are active in winter. Learn how to interpret the tracks and signs or clues of active animals in winter. Stay active and warm with a group challenge about hibernation. Conduct an experiment about snow insulation.
10:00 am to 12:00 pm

Kidleidoscope at Breakheart Reservation

Kidleidoscope is a program designed for preschoolers at Breakheart Reservation in Saugus Massachusetts
Come join our park interpreter for a story time and nature walk! Complete a small craft and explore the woods! Walks are gently paced and approximately 1 mile, though not accessible for strollers. Appropriate for families with children 3-5 years old. Meet at the Visitor Center.
10:30 am to 11:30 am

Unraveling Winters Wild Tales - Animal Tracking for Families

Kids will learn about tracks and signs and how they can tell a story at Ipswich River Wildlife Sanctuary in Topsfield Massachusetts!
Welcome to the wild world of animal tracking! Participants will learn how to identify animal tracks by focusing on key details such as number of toes, toenail impressions, and overall size of the print.
3:00 pm to 4:30 pm

Saturday, January 24

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

Nice n' Easy Hike at Breakheart Reservation

Nice and Easy winter hike at Breakheart Reservation in Saugus Massachusetts
Join the Park Interpreter for this weekly guided hike! Each trip will highlight natural and historic features unique to Breakheart. Hikes are moderately paced and range from 2-3 miles over sometimes uneven and rocky terrain. Best for ages 8 years and up. Meet at the Visitor Center.
9:30 am to 11:30 am

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

Gloucester's So Salty 2026

Celebrate Gloucester Massachusetts recognizably salty character with local cultural institutions in the heart of downtown.
Celebrate the fish city’s recognizably salty character with local cultural institutions and businesses during the 5th Annual Gloucester’s So Salty festival sponsored by the Cape Ann Museum in partnership with Discover Gloucester! This annual event brings over 2,000 people to the downtown area each...
10:00 am to 4:00 pm

Native Seed Sowing at Long Hill

Seed Sowing Workshop at The Trustess of Reservations' Long Hill Gardens in Beverly Massachusetts
Join Cole Campbell, production horticulturist at Native Plant Trust, for this native seed-sowing workshop at Long Hill Public Garden in Beverly, MA. Learn about our native plant seeds, and then get your hands in the soil to sow some seeds that you can take home with you.
11:00 am to 12:30 pm

Sunday, January 25

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
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