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Vineyard Hill Trail Race

Essex County Greenbelt Association hosts a 5k/10k Race at Vineyard Hill in South Hamilton Massachusetts

The Essex County Greenbelt Association is hosting the annual Vineyard Hill Trail Race, featuring both 5k and 10k options. Located on the town line of Hamilton and Topsfield, this 5K/10K course takes runners over Vineyard Hill, through sections of Bradley Palmer State Park, along the Bay Circuit Trail, and across Greenbelt’s scenic Shaw Field. The trails are generally wide and rolling, though Vineyard Hill itself adds a challenge to the course!

When: 
Saturday, August 23, 2025 9am
Race Day Registration Opens at 7:30

Cape Ann Yukan Run Triple Threat Run

The Yukan Run Triple Threat Race Series is a half marathon or 5k.  There's something for everyone in the race series - serious runners, enthusiasts and even walkers are invited to race!  Proceeds from the races go to local charities.  Sign up for one or both, it will be a great morning filled with healthy fun!

When: 
Sunday, August 3, 2025 7am-Noon

Annual Newburyport High Street Mile

The Annual High street Mile includes categories for kids races and is part of Newburyport Yankee Homecoming!

Now in its 32nd year, this one mile road race, occurring during Newburyport's Historic Yankee Homecoming Festival. It features multiple races including a children's heat with medals for all the little finishers! Cash prizes for overall and age group winners! There will be snacks and beverages at the finish line and beer tickets for a free beer and post race viewing party at the Winner's Circle Sport's Bar post race! Proceeds to benefit Winner's Circle Running Club and Newburyport All-Sports Boosters.

When: 
Sunday, August 3, 2025 9-11:30am

Derek Hines Flag Day 5k

Run the Flag Day 5k and raise funds for Massachusetts Veterans who have sustained serious injury in the line of duty

The 1st LT Derek Hines Soldiers Assistance Fund is excited to return to Cashman Park for the 14th Annual Flag Day 5K road race. The 5K walk or run will be hosted on June 14, 2025 at Cashman Park in Newburyport, MA. We look forward to gathering in person this year as we continue to honor 1st LT Derek Hines and provide financial assistance for Massachusetts’ soldiers, and their families, who have incurred serious, career-ending, and life-altering injuries while on active duty.

When: 
Saturday, June 14, 2025 4pm

Annual Walk/Run for HAWC

The annual walk for HAWC in Salem Massachusetts is a major fundraiser for the organization!

HAWC hosts their annual fundraiser run and walk in Salem, Massachusetts.
 Join as as we come together to raise critical funds for HAWC's life saving programs and services while celebrating HAWC's work and the resilience of survivors of domestic/partner abuse. Each year HAWC provides free and confidential services to over 2,000 survivors in 23 cities and towns here on the North Shore.

When: 
Sunday, June 8, 2025 10am-1pm
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: 

Twin Lights Half Marathon

Twin Lights Half Marathon starts at Good Harbor Beach in Gloucester and follows a route along the Gloucester's beautiful back shore.

Come enjoy beautiful ocean views as you run along the scenic coastline on Cape Ann and race towards our huge finish line arch! The Twin Lights Half Marathon offers a spectacular course with the seashore visible for much of the race's 13.1-mile route. Runners will also enjoy an up-close look at many of the sights that have deep roots in the nation's maritime history.

When: 
Sunday, May 4, 2025 9am

Lungstrong 5k & 1.5 Mile Walk

Join the Lungstrong 5k in Beverly Massachusetts

Support the fight against lung cancer and join us for our 10th annual LUNGSTRONG LIVE & VIRTUAL 5K Run & 1.5mi Walk! This family-friendly event gives 100% of race proceeds and donations to Mass General Cancer Center for Thoracic Cancer Research under the direction of Dr. Justin Gainor. MGH is deeply committed to rapidly bringing advances to their patients and is making remarkable progress in identifying genetic mutations and developing targeted therapies for lung cancer. Your participation will help make a difference in the lives of patients today and it is with much optimism that one day lung cancer will be a treatable disease and no longer fatal.

When: 
Sunday, May 18, 2025 10am-1pm

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Landmark Summer Experience at Landmark School in Beverly Massachusetts

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

Marblehead Christmas Walk

The Marblehead Christmas Walk is several days of local Holiday events in Marblehead Massachusetts
The Marblehead Chamber of Commerce invites you to Marblehead to enjoy several days of holiday festivities, family events and activities!  Come for one or all days with highlights that include Santa's arrival by lobster boat,Festive shopping, Tree Lightings, a holiday parade, Artisan Markets,...
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

Deck The Halls: Hammond Castle

A holiday themed tour of Hammond Castle Museum in Gloucester Massachusetts
Travel back in time to a castle filled with lush, opulent textures inspired by the great medieval and Renaissance castles of Europe. Wander through rooms adorned with White Birch and Christmas trees, sparkling fairy lights, hydrangea-lace garlands, and elegant bows, each space transformed with its...
10:00 am to 8:00 pm

Take a Trolley Ride with Scrooge!

Salem Trolley Christmas Carol, Fun Holiday Events north of Boston, Trolley Ride with Scrooge
Join Scrooge on the Salem Trolley as you ride through Salem Massachusetts in this rolling production performed by the Griffen Theater . Now entering into it's 39th Season, this humorous & whimsical interactive performance reanimates Dickens’ timeless seasonal holiday classic. Experience...
2:00 pm to 9:30 pm

CraneExplorer: Family Full Moon Hike in the Dunes

Walk through the Crane Wildlife Refuge in Ipswich Massachusetts with the Trustees under the full moon.
There is almost nothing more peaceful than a evening walk at the Crane Estate, and we would like to invite your family to join us for a unique hiking experience. With the full moon rising over the Atlantic, we’ll start with a sunset stroll along Crane Beach admiring this spectacle before heading...
3:30 pm to 6:00 pm

Friday, December 5

Tree Lighting in Marblehead

Marblehead's tree lighting is always a festive occasion to kick off the holidays
The Tree Lighting will take place at the new National Grand Bank Parking Lot on Pleasant Street in Downtown Marblehead this year!  Enjoy the festive atmosphere and live music as the town lights the yearly Christmas tree! Festivities begin at 5:30pm with the tree lighting at 7pm.
5:30 pm to 7:00 pm

SeaFestival of Trees | Blades Night

Celebrate with holiday with the Bruins Mascot at the SeaFestival of Trees in Salisbury Massachusetts
Come tho the SeaFestival of Tree for a special Bruins themed night! Wear your Bruins apparel, meet the Bruins mascot and skate on the Seaaside Ice indoor rink! Enjoy a scavenger hunt through a maze of sparkling trees, visit Santa, and enjoy the candy cane forest. Skate rentals available. 
6:00 pm to 8:00 pm

Hamilton-Wenham Carol Sing & Tree Lighting

Hamilton-Wenham Community hosts a community carol sing and tree lighting in Massachusetts
The Community House Of Hamilton & Wenham invites children to join us for a jolly evening of carol singing and holiday cheer, led by Kimberly Robertson, Music Director for Stage 284! Santa will be arriving in style at about 7:15pm. Free to attend!
6:30 pm

Saturday, December 6

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

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

Marblehead Christmas Walk

The Marblehead Christmas Walk is several days of local Holiday events in Marblehead Massachusetts
The Marblehead Chamber of Commerce invites you to Marblehead to enjoy several days of holiday festivities, family events and activities!  Come for one or all days with highlights that include Santa's arrival by lobster boat,Festive shopping, Tree Lightings, a holiday parade, Artisan Markets,...
9:00 am to 9:00 pm

Santa Arrives in Marblehead

Come to Marblehead to welcome Santa as he arrives for the Christmas Walk!
Come to the State Street Landing in Downtown Marblehead to welcome Santa as he arrives by lobster boat!  There's plenty of photo ops and Santa's arrival is followed by the Marblehead Christmas Walk Parade. 
9:00 am

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

Christmas at Castle Hill | A Nod to Nature

Christmas at Castle Hill | A Nod to Nature is a weekend of festivities hosted by the Trustees of Reservations at Castle Hill in Ipswich Massachusetts
Visiting Castle Hill at Christmas is a time-honored tradition. Don’t miss this year’s event celebrating the beauty of the natural world. You’ll see birds, flowers, snowflakes, and more as you view 18 spaces decorated for the holidays.
10:00 am to 8:00 pm

2025 Marblehead Gingerbread Festival

The Marblehead Gingerbread Festival is part of the Marblehead Chamber of Commerce's Christmas Walk, and the proceeds will go to benefit the Marblehead Family Fund and the Marblehead Historical Society.
Come see over 100 locally and professionally made gingerbread creations on display at the historic Jeremiah Lee Mansion in Marblehead, MA during this year's Marblehead Christmas Walk. Community members, businesses, and families are building and donating dozens of gingerbread houses, boats and local...
10:00 am to 4:00 pm
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