Gloucester

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

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: 

Gloucester Waterfront Concert & Fireworks 2025

The FREE Annual Independence Day Fireworks Extravaganza Concert on Gloucester Harbor Fourth of July

Gloucester is gearing up for an exciting Independence Day celebration. Experience the beauty of Gloucester’s skyline with a mesmerizing fireworks display. Watch the night sky light up with vibrant colors over popular locations around Gloucester.  

When: 
Thursday, July 3, 2025 5:30pm - 11pm

Gloucester Horribles Parade and Fireworks

Gloucester Massachusetts hosts an annual Horribles Parade to celebrate Independence Day every year on July 3rd.

Gloucester hosts their annual Horribles Parade followed by a concert and fireworks over Gloucester Harbor! The parade will follow its traditional route out Centennial Avenue, left on Western Avenue to Washington Street at Tally’s Corner, right down Washington and left onto Rogers Street, left on Manuel F. Lewis Street, then a left up Main Street and a right up Pleasant Street to Prospect Street, the left on Prospect, right on Railroad Avenue and a right onto Washington Street, finishing with a left onto Centennial Avenue back to Gloucester High School.

When: 
Thursday, July 3, 2025 6pm-11pm

Saint Peter's Fiesta | Saturday

A highlight event at St. Peter's Fiesta in Gloucester, MA is the infamous Greasy Pole contest near Pavilion Beach

The Saint Peter's Fiesta is an annual festival in Gloucester, Massachusetts celebrating the city's fishing heritage, close-knit families, community, and religious traditions.  The five-day celebration includes a carnival, live entertainment, and unique traditional events like the infamous 'Greasy Pole' contest and classic seine boat races. The festival is proudly sponsored by the Italian-American fishing community of Gloucester, and has all kinds of family-oriented activities and events, making it a great early Summer destination weekend event.

When: 
Saturday, June 28, 2025 10am-Midnight

The Backyard Growcery

Join Backyard Growers at Burnham's Field in Gloucester Massachusetts for a weekly Farmer's Market

Stop by Gloucester’s new weekly farmers market, the Backyard Growcery, managed by Backyard Growers. The Backyard Growcery is located at Burnham's Field, an urban park near Gloucester’s thriving waterfront, and features small-scale North Shore farmers, bakers, a seafood vendor, an artisanal pizza maker, and more, throughout the season.

When: 
Wenesdays, June 18 - October 15, 2025 2:30-6pm
Location: 

Historic Dogtown: A Walk Back in Time

Hike the trails of Dogtown in Gloucester Massachusetts with Cape Ann Museum

On Cape Ann, the name “Dogtown” conjures up many things — vast woodlands and trails; stone walls and cellar holes; tales of witches and widows; an ill-fated bullfighter; pastures, picnics and blueberries; a sea of rocks. Dogtown is all of these things and more. But first, it is a place where proud people once lived and worked, at the center of Gloucester, for nearly 150 years – until it became “Dogtown” and died out.

When: 
Sunday, June 1, 2025 10am-Noon
Location: 

Full Moon Hike at Ward Reservation

Join the Trustees on a journey up Holt Hill under the light of the full moon at Ward Reservation in Andover!

Join the Trustees for an evening journey up Holt Hill under the light of the full moon. Together, we will trek up the trail as night falls, and gather at the top beneath the moon & stars. Enjoy the sights, sounds, smells, and unique tastes of evening in the magic of Ward Reservation. We will share stories and tales about the moon and its effect on people throughout time.

When: 
Tuesday, June 10, 2025 7:30-9:30pm
Location: 

Explore! North Shore – Trails Day Hike at Ravenswood

Giant boulders can be found all over Ravenswood Park. How'd they get there?

Join the Trustees to celebrate National Trails Day with a guided hike of Ravenswood Park in Gloucester. On this intermediate hike, you will enjoy a ~3 mile loop with moderate elevation gain, as you are guided up the rocky and narrow Ledge Trail up to a scenic overlook of the harbor and then descend via the broader and flatter Salem Road carriage path trail. You’ll pass through an old quarry, rocky trails lined with beech, pines, ferns, and rare wetland plants. This glacier-shaped landscape provides shelter for a variety of wildlife, look for scat, tracks and dens along the trail! Our naturalist guides will share the human and natural history of this property, including how the Trustees maintains the properties many trails for all to enjoy.

When: 
Saturday, June 7, 2025 10am-1pm
Location: 

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Appleton Farms offers great farm-based Vacation Week Programs for kids ages 5-11

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

StoryWalk Series at Maudslay

“Magnificent Monarchs” by Linda Glaser Storywalk at Maudslay State Park in Newburyport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! “Magnificent Monarchs” by Linda Glaser is featured in this StoryWalk Series. Younger kids will love this gentle, richly illustrated children’s nonfiction book aimed at preschool–third grade...
7:00 am to 8:00 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

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

Amesbury Days Celebration

Amesbury Days is a celebration of the onset of Summer and community.
Amesbury Days is a a 8-day celebration of all things Amesbury that kicks off the summer with fun and exciting community events in Amesbury, Massachusetts. Fireworks, a block party and a 5k walk/run will be just some of the highlights of this years' Amesbury Days celebration. There will be events...
9:00 am to 9:00 pm

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 4:00 pm

Sing & Dance with the Music Man

Sing & Dance with the Music Man Brian Doser in Hamilton visit Massachusetts
Come join the fun at Community House Of Hamilton & Wenham Monday, Thursday and Saturday mornings at 10am for 30 - 45 minutes of great music with Brian Doser! Sing and dance with the Music Man during a family concert, featuring familiar and original tunes, performed by local dad and musician,...
10:00 am to 10:45 am

Beverly Farmers' Market

Get fresh local produce at the Beverly Farmers Market in downtown Beverly Massac
The Beverly Farmers’ Market supports local agriculture while making healthy food available to all members of the Beverly community at affordable prices; the market promotes sustainable living practices and fosters community connections through our vendors, free activities and events. The market...
Where: Odell Park
3:00 pm to 7:00 pm

Music in the Millyard: Studio Two Beatles Tribute

Studio Two is a Beatles cover band that will play at Amesbury Town Park.
Studio Two is a headlining Beatles band that pays tribute to the early Beatles years, choosing songs from the pre-Sgt. Pepper era. Featuring graduates from Berklee College of Music and Beatles devotees, Studio Two band mates met in a “cellar full of noise” in a town slightly west of Liverpool (...
7:00 pm to 8:30 pm

Tuesday, July 1

StoryWalk Series at Maudslay

“Magnificent Monarchs” by Linda Glaser Storywalk at Maudslay State Park in Newburyport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! “Magnificent Monarchs” by Linda Glaser is featured in this StoryWalk Series. Younger kids will love this gentle, richly illustrated children’s nonfiction book aimed at preschool–third grade...
7:00 am to 8:00 pm

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

Amesbury Days Celebration

Amesbury Days is a celebration of the onset of Summer and community.
Amesbury Days is a a 8-day celebration of all things Amesbury that kicks off the summer with fun and exciting community events in Amesbury, Massachusetts. Fireworks, a block party and a 5k walk/run will be just some of the highlights of this years' Amesbury Days celebration. There will be events...
9:00 am to 9:00 pm

Powow Scenic Vista Hike

Take a Trails & Sails hike to the top of Powow Hill in Amesbury Massachusetts!
Come join the Lake Gardener Improvement Association for a guided up Powow Hill, at the summit of the highest peak on the Essex County Seacoast! This short, slow paced hike will take us from the shores of Lake Gardner through the Powow Conservation Area, to the park, created 100 years ago!
9:00 am

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 4:00 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

Kids Night at the Millyard

Amesbury Days hosts a night of fun for kids of all ages in the Upper Millyard in downtown Amesbury
Amesbury Days hosts a night of fun for kids of all ages! DJ Dance Party, Magician, Photo Booth, Games, Food & More. Join us for a magic show from 5:30-6:15 followed by a DJ Dance Party from 6:15-7:30, food, ice cream, games, balloons, face painting, and much more! 
5:30 pm to 7:30 pm

Ipswich Downtown Tuesdays

Ipswich Downtown Tuesdays includes great dining live music, dancing & extended shopping hours for shopping Downtown Ipswich Massachusetts Tuesday evenings!
Ipswich Downtown Tuesdays includes great dining, live music, dancing at the Take-Out Terrace Stage on the Riverwalk  & extended shopping hours for shopping Downtown Ipswich Tuesday evenings!  Each week will feature live entertainment on the Riverwalk, making for a fun evening out for the whole...
6:00 pm to 8:00 pm
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