Essex

Boston Bruins Annual Pajama Drive

Drop off new pajama donations at libraries across the North Shore of Massachusetts as part of the Boston Bruins PJ Drive.

The Boston Bruins will be hosting their 19th annual PJ Drive with the goal of collecting 10,000 pairs of pajamas from February 1st - March 15th, 2026. The drive will benefit Cradles to Crayons and Wonderfund MA, two non-profits that ensure positive living conditions for children. Local businesses and organizations can register to host their own drive and fans are encouraged to help by purchasing a donation from Cradles to Crayons' Amazon Wishlist.

When:

February 1 - March 15, 2026

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Essex Firemen's Spaghetti Supper

Come to the Essex Massachusetts Fire Deaprtment for the annual spaghetti fundraiser!

The Annual Essex Fire Department Company Spaghetti Supper is A great night to enjoy a home-cooked meal with neighbors and friends while supporting a great cause! The town’s volunteer firefighters put out quite a spread of all-you-can-eat homemade spaghetti and meatballs accompanied by salad, beverage and dessert. Everyone welcome! Donations accepted at the door. Winter boots and coats will be collected to help those in need. Your generosity will be greatly appreciated.

When:

Saturday, November 22, 2025 4-7pm

Location:

Essex Fire Department

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Fall Foliage Cider & Donut Cruises

Take a guided tour of the Essex Massachusetts Marshes with Essex River Cruises this Autumn

Essex River Cruises hosts a narrated sightseeing tour that winds down the beautiful Essex River aboard Essex River Queen, a pontoon boat. We’ll cruise up close to Hog/Choate Island to get a view of the area's magnificent dark spruce forest. See the leaves change into brilliant hues of yellow and orange. Enjoy complimentary hot cider and donuts from Russell Orchard of Ipswich. Don’t miss this magnificent opportunity to view some of New England’s most spectacular fall foliage.

When:

Saturdays & Sundays through October 2025 1-3 pm

Monday, October 13, 2025 1-3pm

Location:

Essex River Cruises & Charters

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Essex Turkey Trot 5K Race & Fun Walk

The Essex Massachusetts Lions host their annual 5k Turkey Trot!

The Essex Lion's Club hosts the annual turkey trot in beautiful Essex Massachusetts! This year the race is a 5K and a 5k fun walk. Race starts at 11:00am for runners and 10am for walkers. Registration is at Woodman’s Restaurant (upstairs), 121 Main Street, Essex, from 9:30 am to 10:30 am, or pre-register online.

When:

Sunday, November 23, 2025 10am

Location:

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Overlooking the Essex River Tour

Tour Cogswell's Grant Coastal Farm in Essex Massachusetts as part of Trails & Sails

On this walking tour, explore the landscape history at Cogswell’s Grant in Essex, Massachusetts, from the presence of indigenous people through the colonial period to the present. Walk through hayfields down to the salt marsh and the Essex River, discover the rich history of the people and families who lived and farmed here, and learn how coastal farming has evolved over the centuries. Part of Trails & Sails. Reservations Required

When:

Saturday, September 27, 2025 11am-12:30pm

Location:

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Kite Day at Cogswell's Grant

Kite Day at Cogswell Grant is a wonderful fall afternoon event for North Shore families

Come fly a kite at Cogswell's Grant in Essex Massachusetts! Bring your own kite or build one of your own, and watch professional kite flyers from Kites Over New England. Kite-building workshops will be held with all materials included, where kids and adults can make their own kites and learn how to fly them.

When:

Saturday, September 13, 2025 10am-4pm

Rain Date, September 14, 2025

Location:

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Happy as a Clam 5k & Kid Fun Run

The Happy as a Clam Road Race invites children and families to race in Essex

The 15th Happy as a Clam 5k Race, Walk and Fun Dashes - powered by Great Marsh Brew Co, our exclusive Flagship Sponsor - is Friday, September 15, 2023! This event is open to anyone who wants to support a community school and all the wonderful enrichment programs the students hope to enjoy throughout the year. The 5K route meanders through the beautiful back roads of Essex. The Kids' Fun Dashes are always a hit, with even the littlest ones smiling from start to finish. Come out, lace up, and pound the pavement for the students of EES. It's sure to be another fun race this year!

When:

Friday, September 12, 2025 5pm

Location:

Essex Elementary School

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July 4th Boat Parade in Essex

The Chebacco Boat Parade is a great Fourth of July tradition in Essex MA

The Chebacco Lake and Watershed Association will sponsor its annual Fourth of July Boat Parade on at 10am Sunday, July 4th. All boats will meet at Gregory Island Cove on the South Side of Gregory Island (small cove) and proceed around the lake counterclockwise. Prizes will be awarded for Most Patriotic, Most Creative and best costume or costumes.

When:

Friday, July 4, 2025 10am

Location:

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Essex River Day

Essex River Day 2025 is CANCELED - No Rain Date! Essex River Day was created to celebrate one of our most valued resources - the Essex River. This simple idea has grown into an annual event to kick-off the start of summer! Head down to Memorial Park at 24 Martin Street next to Essex Town Hall on Saturday, June 17th from 5pm-9pm (Rain Date: Sunday, June 18th) for live music by Brick House, games by Ipswich Family YMCA, 5 Star Phresh Phood truck, brews from our own Great Marsh Brewery and a bonfire lit at dusk. Special thanks to Greater Cape Ann Chamber of Commerce and Essex Lions Club for their event support.

When:

Wednesday, June 14, 2025 5-9pm

Location:

Memorial Park (Essex)

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Magical Beginnings Learning Centers

Magical Beginnings has numerous learning center locations on the North Shore of Massachusetts

At Magical Beginnings Inc., we provide a nurturing, high-quality childcare experience designed for the North Shore families who demand excellence. Our innovative environment encourages children to explore their creativity, build social skills, and achieve key developmental milestones through play and interactive learning. We foster an inclusive community where infants, toddlers, and preschoolers enjoy individualized schedules and multi-age classroom settings, promoting peer learning and long-lasting relationships. With a strong focus on safety—including a strict nut-free policy—and active parent engagement through platforms like Class Dojo, we ensure that every day is both enriching and secure for your child.