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

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: 

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: 

Annual Plant Sale | Generous Gardeners

Generous Gardeners is having a plant sale just in time for the growing season in Gloucester Massachusetts!

Generous Gardeners is having a plant sale to just in time for the growing season in Gloucester Massachusetts! Join us for a Plant Sale on Stacy Boulevard on Saturday, May 17, 2025 from 9am to noon. The event will be held rain or shine. Locally grown plants plus dahlia tubers will be available for sale.

When: 
Saturday, May 17, 2025 9am-Noon
Location: 

Bluefin Blowout Family 5k to Benefit Alzheimer's Association

The Bluefin Blowout Family Fun Run in Gloucester Massachusetts raises funds to combat the diseases of Alzheimer's and all other dementias

On Sunday, May 18th, 2025, come to Stage Fort Park, Gloucester for the Bluefin Blowout Family Fun Run 5K, Presented by the Lyon-Waugh Auto Group - Benefiting the Alzheimer’s Association. Run, walk, or stroll from Stage Fort Park to Hammond Castle and back to Stage Fort Park for a 5K loop. Enjoy the beautiful Cape Ann waterfront and fresh ocean air while raising money for the Alzheimer’s Association.

When: 
Sunday, May 18, 2025 7am
(race starts at 8:30)
Location: 

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Summerquest Camp for kids aed 5-14 at the Crane Estate in Ipswich Massachusetts

Todd Farm Market

Come to Todd Farm on Sunday - A classic New England Fleas Market in Rowley Massachusetts!
From early Spring to late Fall, Todd Farm is a great Sunday destination for families!  Head to the farm and explore the outdoor award-winning Market featuring up to 240 vendors from all over New England and New York!
5:00 am to 3:00 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

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

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

The Lady of Salem: Maritime Art

Learn about the history of Salem Massachusetts through this unique public art installation self-guided tour!
Discover Salem’s Golden Age of Sail as you uncover clues! Celebrate America’s Maritime History! The Ladies of Salem will have you looking up at whimsical and beautifully designed figureheads gracing lampposts downtown. “What is a figurehead ?” you may ask? It’s a large carved wooden decorative...
8:00 am to 10:00 pm

Rowley Farmers Market

Rowley Farmers Market - a seasonal open-air market every Sunday July-September on Rowley Common
The Rowley Farmers Market is an open air market held on Sundays on the Rowley Town Common.  There's always a great selection of fresh local produce, food stuffs and locally hand-made goods. Come pick up some great locally grown food, freshly baked bread by Faith Anne's Unique bread, specialty teas...
9:00 am to 1:00 pm

Newburyport Farmers' Market

Newburyport Farmers find organic locally grown produce, meat, dairy Newburyport
The Newburyport Farmers Summer Market celebrates local fresh produce every Sunday morning rain or shine!  Start your Sunday browsing fresh North Shore local produce, meats, cheeses, and seafood in an open air market atmosphere! Food and beverage vendors offer fresh hot coffee, breakfast treats and...
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

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...
9:00 am to 6:00 pm

North Andover Farmers' Market

North Andover Farmers Market every Sunday Through October 2, 2022
The North Andover Farmers Market is the perfect destination for anyone living in the Merrimack Valley or the North Shore to shop and enjoy locally-sourced products. The market will take place in the center of town at the intersection of First Street and Main Street. The market has become known for...
10:00 am to 1:00 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

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

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

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...
1:00 pm to 4:30 pm

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...
1:00 pm to 3:30 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

Sunday STEAM Club at North Shore Children's Museum

Visit Peabody MA, NorthShore, North Shore Children's Museum
Join in on Sundays at 2:30 for STEAM Club for ages 5-11. Each week participants will explore science, technology, engineering, art, and math with our NSCM staff! Every STEAM club session will see your kids participating in hands-on activities while exploring a new topic. Space is limited, please...
2:30 pm to 4:00 pm

Sundays in Patton Park

North Shore Free Concerts for North Shore Families at Patton Park in Hamilton Massachusetts
Come enjoy community and music each Sunday in Patton Park! Dust off your lawn chairs and bring your picnic down to the park on Sunday evenings. We have a fantastic line up of bands this summer ---presented by Institution for Savings Bank and sponsored by The Community House, Town of Hamilton, HW...
5:00 pm to 7:00 pm

Summer Concert Series at Lynch Park

Free Summer Concerts hosted by Bev Rec at Lynch Park in Beverly Massachusetts
Enjoy free concerts this Summer at Lynch Park in Beverly, Massachusetts!  Families are encourages to grab a chair and a blank and head to the park for a free concert at Lynch Park's ampitheater.
Where: Lynch Park
6:00 pm to 8:00 pm

Tuesday, August 19

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

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

Tuesdays are for Everyone at Salisbury Beach

Tuesdays are for everyone special events and activities at Salisbury Beach in Massachusetts
Come to Salisbury Beach every Tuesday, July through August for FREE seaside, family friendly activities! Starting July 11th, every Tuesday, thorugh August 22 there will be free family friendly programing at the Salisbury Beach Center.
10:00 am to 8:00 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

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

Wednesday, August 20

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

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
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