All Ages

Downtown Gloucester Block Party

Food, music, live entertainment, dance, craft and fun come together for a great

Main Street, Downtown Gloucester Massachusetts comes alive when the Street is closed off to allow live music, street performers, kid activities, non-profits, food vendors and more! Many of shops and businesses on Main Street will be open for business and will welcome partygoers. Other Gloucester businesses and non-profits will be represented on the Street as well. come for a night full of Live music, great food, and fun activities with lots of local flavor!

When: 
Saturday, July 12, 2025 6-10pm
Saturday, August 9, 2025 6-10pm
Friday, August 29, 2025 6-10pm

Heritage Day in Gloucester

Maritime Gloucester & Ocean Alliance hosts a day of free exciting demonstrations and interactive fun for all ages in Gloucester Massachusetts.

Maritime Gloucester is hosting their annual Heritage Day in honor of the Gloucester Schooner Festival 2025. Step aboard a schooner, learn about traditional shipbuilding and fitting out, watch America’s oldest marine railway in action, or explore the unique biology that makes our oceans so amazing. You can find it all at Maritime Heritage Day! Maritime Gloucester will be hosting a variety of local community organizations with an exciting array of demonstrations and interactive options for all ages.

When: 
Saturday, August 30, 2025 10am-4pm

Schooner Festival Fireworks

The Gloucester Schooner Festival will light up Gloucester Harbor with Fireworks!

Following the Gloucester Schooner Festival's Parade of lights in Gloucester Harbor, A fireworks display will light up the sky over Gloucester Harbor to celebrate a great day of maritime history and tradition.  Good vantage points for viewing fireworks include Gloucester's Boulevard, Stage Fort Park, Pavilion Beach

When: 
Saturday, August 30, 2025 9:15pm

Gloucester Waterfront Festival

Come to Stage Fort Park in Gloucester Massachusetts for the Annual Waterfront Festival.

Get ready for a weekend of art, flavor, and seaside charm as the 44th Annual Gloucester Waterfront Festival returns to the historic Stage Fort Park on August 16 & 17, 2025. Set against the stunning backdrop of Gloucester Harbor, this beloved festival invites visitors to explore an extraordinary array of over 200 juried booths featuring American-made arts, crafts, specialty foods, and more! 

When: 
Saturday, August 16, 2025 9am-6pm
Sunday, August 17, 2025 9am-5pm
Location: 

Summer Concert Series at Stage Fort Park

Compaq Big Band is just one of the perfromers in the Summer Concert Series at Stage Fort Park in Gloucester Massachusetts!

Come enjoy a Summer evening sea-side concert at Stage Fort Park in Gloucester Massachusetts! The Cape Ann Community Band under the direction of David Benjamin, plays their annual summer concerts Sundays at the at the Antonio Gentile Bandstand, Stage Fort Park, Hough Avenue, Gloucester MA.

When: 
Sundays, July 6-August 24, 2025 6:30pm
Saturday, August 16, 2025 6:30pm
Location: 

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

Bike Safety Rodeo at Lynch Park

Kids and families are invited to Lynch Park in Beverly Massachusetts for a the bike safety rodeo hosted by Beverly Police!

Free! Fun safety course, bike inspections, and free helmets in the parking lot at Lynch Park. The George Robertson memorial bike rodeo is hosted by the Beverly Police Department, with generous contributions by the Beverly Kiwanis. All who attend will be instructed in bicycle safety, and all can participate in a safety obstacle course. There will also be bike inspections, free helmets (quantities limited) and more!

When: 
Friday, August 8, 2025 4-6pm
Location: 

Beverly Homecoming Kids Carnival

Lynch Park in Beverly Massachusetts becomes a midway of carnival kids games during Beverly Homecoming!

Get ready for a day of festive fun at the Lynch Park Carnival! Join BevRec for an exciting event packed with thrilling games, delicious treats, and a lively atmosphere. Bring your children to experience the joy and wonder of a classic carnival. Indulge in cotton candy, test your skills at various game booths, and enjoy the vibrant entertainment and activities. There’s something for every child, so mark your calendars and join us for an unforgettable day at the Lynch Park Carnival! Game tokens are available on site for purchase. Cash only

When: 
Friday, August 8, 2025 10am-2pm
Location: 

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

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

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

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

Crescent Farm Corn Maze

Crescent Farm corn maze in Haverhill Massachusetts
Imagine the biggest puzzle you’ve ever seen. Now imagine a day in the sunshine with your friends or family. Now add an adventure that takes teamwork and memory skills. All these things and more can be found at Crescent Farms Corn Maze. Crescent Farm Corn Maze trails cut into 9 acres of corn. Inside...
9:00 am to 9:00 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

Gloucester Gratis Days at Hammond Castle

Bring your kids to the Hammond Castle Museum in Gloucester Massachusetts during April Vacation
In keeping with John Hays Hammond, Jr's original vision for his seaside castle-home to serve as a museum offering the Gloucester community access to ancient works of architectural art, Hammond Castle Museum will offer Gloucester residents free, self-guided tours each Tuesday throughout the regular...
10:00 am to 4:00 pm

Saturday, September 13

Visit the Manchester-by-the-Sea Museum

Manchester-by-the-Seab Museum tours in Massachusetts. A Trails and Sails event.
Discover Manchester-by-the-Sea’s history, architecture & art through our exhibits, tours & collections.
10:00 am to 4:00 pm

Waterpower at the Saugus Iron Works Tour

Free Ranger guided tours at Saugus Iron Works Colonial Industrial Site in Massachusetts
How did water drive early industries in colonial Massachusetts? Join a park ranger for a special tour focused on waterpower at the Saugus Iron Works in Massachusetts. Hear the crash of the hammer and the bang of the bellows as we demonstrate a variety of waterwheels at the Iron Works. Learn how...
10:00 am to 1:00 pm

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...
11:00 am to 2:00 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

Farm-Forest-Ice Cream Hike

Join this Trails and Sails Hike through the woods in Ipswich for an ice cream treat! A Sails & Trails event.
A group hike from Marini Farm through the forest to White Farms for an optional ice cream. Don’t miss this great opportunity to explore the farm, forest, and nature of Ipswich. The group will meet on Linebrook Road in Ipswich. Bike entrance to Willowdale State Forest just west of Marini Farm.
11:00 am to 2:15 pm

Saugus Iron Works House Tours

Free Ranger guided tours of the Saugus Iron Works House in Massachusetts
Join National Park staff at Saugus Iron Works National Historic Site for a 30-minute tour of The Iron Works House.
11:00 am

Farm Days Festival

Farm Days is a family event held at Appleton Farms in Ipswich Massachusetts
Join us for our Annual Fall Celebration at Appleton – Farm Days! Spend the afternoon exploring the farm, listening to music, enjoying great food & beer, hiking our trails, entertaining the kids and more. Please Note: Tickets are per vehicle, not per person, and include access to the farm and...
12:00 pm to 5:00 pm

Team Haverhill’s River Ruckus

Come celebrate Haverhill's River Front at the River Ruckus in Haverhill Massachusetts!
Team Haverhill’s River Ruckus is an annual festival featuring live music, classic cars, Kids Zone, great local foods, and spectacular fireworks over the Merrimack River. Presented by Team Haverhill, a community-based volunteer organization, the festival attracts over 5,000 visitors and residents...
12:00 pm to 8:30 pm

Plumfest 2025

Plumfest is an annual celebration of music and community on Plum Island in Newburyport
PlumFest is a non-profit volunteer-run organization incorporated as a Charitable Foundation to bring local musicians, island residents and visitors together to showcase the natural beauty and artistry that make Plum Island such a special place. As an early participant in the “porch-fest” movement...
12:00 pm to 6:00 pm

Family Day at the Industrial History Center!

Open House at the Amesbury Carriage Museum and Industrial History Center Massachusetts - a Trails and Sails Event
Join Amesbury Carriage Museum for a hands-on fun-filled day for the whole family at our Open House! Try out our hand-powered machines – test your skills at drilling or winding a bobbin, just like workers did in the mills!
12:00 pm to 4:00 pm
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