Gloucester

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

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: 

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: 

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

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

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

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

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: 

Pages

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

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

Newburyport Yankee Homecoming Marketplace

Shop to your heart’s content in our open air bazaar-like market place right in the heart of historic Newburyport’s center. Covering two square blocks, this extravaganza of food and great finds is sure to tantalize all your senses.
10:00 am to 8:00 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

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

Circus Smirkus | 2025 Big Top Tour

Theater in the Open proudly hosts Circus Smirkus' 2025 Big Top Tour in Newbury Massachusetts!
Theater in the Open proudly hosts Circus Smirkus' 2025 Big Top Tour! Every summer, a freshly auditioned company of Smirkus Troupers, ages 10 to 18, take to the road in traditional mud show fashion for a two-month performance tour of New England. Backed by professional coaches, cooks, musicians and...
1:00 pm to 9:00 pm

Saugus Iron Works Tours

Free Ranger guided tours at Saugus Iron Works Colonial Industrial Site in Massachusetts
Join the National Park staff at Saugus Iron Works National Historic Site for a tour of the colonial industrial site. On select days, you may be able to stick around and witness pop-up molten iron pour, blacksmithing, waterwheel demonstrations, and take part in hands-on river stewardship activities.
2:00 pm

Friday Night Party at Salisbury Beach

Salisbury Beach Summer Beach Party every Friday through the Summer.
Get ready for family fun every Friday night all summer long at Salisbury Beach! Starting at 7:15 PM on the Salisbury Beach stage, enjoy a full evening of summer tunes and excitement. DJ Ralphie B will be spinning your favorite hits, while hosting kid-friendly activities that will keep everyone...
7:15 pm to 10:00 pm

Waterfront Concert: Fortune

Fortune will fill the waterfront with music for Yankee Homecoming in Newburyport Massachusetts
Fortune will fill the waterfront with music for Yankee Homecoming in Newburyport Massachusetts! For well over two decades, Fortune has regularly packed venues throughout New England. Hailing from Peabody, MA, this 6-piece band has long maintained a reputation for smooth three and four part vocal...
7:30 pm to 9:00 pm

Saturday, August 2

Salem Heritage Days Festival

Salem Heritage Days is a week long celebration of Salem's history and tradition.
Celebrate the past and the present with neighbors, friends and visitors at the Annual Salem Heritage Days Festival. Events are scheduled around Salem throughout the week, kicking off with the annual Salem Maritime Festival and concluding with the Essex Street Fair, produced by the Salem Chamber of...
7:00 am to 9:00 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

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

Haverhill Farmers' Market

Haverhill Farmers Market, North Shore Farmers Market, Cape Ann Farmers Marke
The vibrant, colorful Haverhill Farmers Market is where local farmers and food producers meet to sell directly to the community. Established in 1978, the Haverhill Farmers Market mission is to provide access to farm-fresh products and promote local agriculture, as well as serve as a social...
9:00 am to 1:00 pm

Marblehead Farmers' Market

Find fresh local produce and other foods at the Marblehead Farmer's Market!
The Marblehead Farmer's Market boasts 15+ local farms, and booths with an educational spin nutrition, vendors and farms selling homemade prepared goods and craft vendors that are switched up in a rotation basis week to week. Additionally there are entertainers and exhibits by environmentally...
9:00 am to 12:00 pm

Andover Farmers' Market

Find Fresh Local Produce at the Andover Massachusetts Farmers Market North of Boston
The Andover Farmers Market is a vibrant hub connecting local farmers, artisans and the community through the joy of local food. Whether you come for carrots or conversation, it is a place to nourish the body, mind and spirit.
9:00 am to 1:00 pm

Rockport Farmers' Market

The Rockport Farmers' Market runs every Saturday at Rockport Music in Downtown Rockport!
The Rockport Farmers Market offers a variety of locally-grown produce, hand-crafted products, baked goods, and live music. It provides a community space to support local farmers and artisans.
9:00 am to 1:00 pm

Crane Outdoors: Kayak Adventure on the Castle Neck River

Take a guided kayak paddle adventure on the Castle Neck River with the Trustees of Reservations!
One of the best was to enjoy the natural beauty of the Massachusetts North Shore is kayaking the placid waters of the Great Marsh—the largest continuous stretch of salt marsh in New England, extending from Cape Ann to New Hampshire. The Castle Neck peninsula on the Crane Estate is a vast barrier...
9:00 am to 5:00 pm
Subscribe to Gloucester