All Ages

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

Climb Up Gloucester City Hall Tower

Take a Free tour of Gloucester Massachusetts City Hall's renovated tower as part of Trails and Sails 2024!

Experience the WOW factor when you climb up Gloucester’s City Hall clock and bell tower and emerge at the bell level. Views, weather permitting, are awesome. Members of Gloucester’s City Hall Restoration Commission will be on hand to inform you of the history of this architecturally significant building that had graced Gloucester’s skyline for more than 150 years. Please note that while the tower is not handicapped accessible the WPA Murals in City Hall are accessible and are one, if not, the best collection of WPA murals in the Commonwealth.

When: 
Saturday, September 27, 2025 Noon-3pm

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

Maritime Adventure Days

Maritime Adventure Free Days at Custom House Maritime Museum Newburyport Massachusetts

Maritime Adventure Free Days offers families and kids a unique opportunity to explore maritime history through interactive activities, guided tours, and hands-on workshops. A day of fun and discovery at the Custom House Maritime Museum for the family. These free Saturday events include experiencing a traditional Wampanoag dugout canoe being made by a team of craftsmen. Part of Trails & Sails

When: 
Saturday, September 13, 2025 9am-1pm
Saturday, September 20, 2025 9am-1pm
Saturday, September 27, 2025 9am-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: 

Step Aboard the Friendship of Salem

Permission to come aboard the Friendship of Salem is granted at Derby Wharf in Salem Massachusetts!

Explore the FRIENDSHIP OF SALEM, a replica tall ship based on a 1796 Salem vessel at Salem Maritime National Historic Site. Learn about the voyages of the original FRIENDSHIP and the lives of the crewmembers onboard. The two-decked, three-masted, square-rigged, 342-ton vessel represents New England’s influential role in the development of global and domestic maritime trade. Ongoing repair work is taking place on the FRIENDSHIP, so capacity limits are in place on deck.

When: 
Wednesday - Sunday, September 13-28, 2025 1:30-4:30pm

Salisbury Days Car Show

Come to Salisbury Beach Massachusetts for a classic car show that lasts all weekend!

Calling all fancy cars, motorcycles, and those that love them! Salisbury Days is hosting a classic car & motorcycle show at Salisbury Beach, along and around the Broadway Loop. Hope to see you there! No registration required. FREE for spectators and Exhibitors. Trophies for Peoples Choice & Best in Show. ALL music - Live streamed from @Tayles & Co Radio / Cool 94.1. Show to run in conjunction with other Salisbury Days events and Trails & Sails

When: 
Saturday, September 20, 2025 10am-2pm

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

AtlAtl Days in Danvers!

See an ancient weapon demonstration at the Rebecca Nurse Homestead in Danvers Massachusetts as part of Trails and Sails!

Come to Rebecca Nurse Homestead to try your hand at ancient hunting practices! The technique of using an atlatl, or spear throwing stick, is an ancient global technology. Join us, along with the Eugene Winter Chapter of Mass Archaeological Society, as they teach you the finer points about hunting in the ancient world! Stop by the Rebecca Nurse Homestead and hunt a woolly mammoth or woolly rhinoceros. Fun and educational for adults and kids of all ages. Wooly mammoth tooth and mastodon tooth and tusk will be on display along with samples of Native American Artifacts found in Danvers. This event is FREE as part of Trails & Sails! If you would like to visit the Nurse Homestead museum, paid admission is required.

When: 
Saturday, September 20, 2025 9am-3pm

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