Holiday

Middle Street Walk Gingerbread Contest 2025

Middle Street Walk Gingerbread Contest entries can take any shape.

Everybody is invited to enter the Gingerbread Contest for the Middle Street Walk in Gloucester this year! Groups and individuals are encouraged to get creative and come up with entries that can take any shape.  All entries will be judged prior to the start of the Middle Street at 10am. 

When: 
Saturday, December 13, 2025 10am - 3pm

Cape Ann Symphony Holiday Pops

Cape Ann Symphony Holiday Pops Concert in Ipswich and Manchester Massachsusetts

Celebrate the Holidays on Thanksgiving weekend with the Cape Ann Symphony conducted by Yoichi Udagawa. The annual Holiday Pops is a musical celebration of the season. The Cape Ann Symphony Chorus now under the direction of Brittany Betts will join the orchestra for a Holiday Pops series for the whole family. The ever popular audience sing-along concludes the performance.

When: 
Saturday, November 29, 2025 2PM [Ipswich]
Saturday, November 29, 2025 7:30pm [Manchester]
Sunday, November 29, 2025 2pm [Manchester]

Middle Street Walk in Gloucester

The lighting of the Lobster Trap Tree is part of Middle Street Walk's finale in Gloucester Massachusetts.

The Annual Middle Street Walk is a great way to experience Gloucester's Historic District and waterfront while having Holiday fun with the family. An updated schedule of this years walk will is available for download at this link.

When: 
Saturday, December 13, 2025 9am - 5pm

Trick or Treating Hayrides at Marini Farm

Trick or Treating by hayride at Marini Farm in Ipswich Massachusetts is Safe and Fun!

Come to Marini Farm for our most popular event of the year. Take a Hayride around our 7 acre corn maze. Your hayride driver will make some special stops along the way. Favorite costumed characters await the wagon to hand out Tricks and Treats. Hayrides run continuously from 10am to 4pm. Riders are welcome to wear costumes. Also includes admission to the Maze Park/Corn Maze area.

When: 
Saturday, October 18, 2025 10am-4pm
Sunday, October 19, 2025 10am-4pm
Location: 

Will Run for Pie - Turkey Trot 5K Run/Walk

Winner's Circle Running Club Annual Thanksgiving 5k in Salisbury Massachusetts

Will Run for Pie 5K – Thanksgiving Morning Tradition. Kick off your holiday with speed, smiles, and slices! The Will Run for Pie 5K Turkey Trot is a flat, fast, and festive race along the beautiful Ghost Trail in Salisbury, MA. Whether you’re chasing a PR or just here for the pie, this is the perfect way to start Thanksgiving morning.

When: 
Thursday, November 27, 2025 8:30-10am

Beverly Pumpkin Smash

Join the fun of the post Halloween pumpkin smash at Moraine Farm in Beverly Massachusetts

Green Beverly is excited to host our Beverly Pumpkin Smash! Bring your pumpkins to New Entry at Moraine Farm, and participate in our composting event! Enjoy the beautiful farm scenery while you launch your pumpkins from a trebuchet into a giant compost pile!  We also offer classic lawn games and products from local businesses.  In 2022 we diverted 40+ tons of CO2 and 30,000 pounds of organic waste from landfills. Come join the fun with and expected crowd of 2000 or more for another 'smashing' event!

When: 
Sunday, November 9, 2025 11m-2pm
Location: 

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: 

SeaFestival of Trees in Salisbury

The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s Workshop, and an indoor skating rink. The festival runs weekends through December 7, with additional special event nights throughout the season.

When: 
Saturdays, November 22-December 6, 2025 11am-8pm
Sundays, November 23-December 7, 2025 11am-5pm
Tuesday, November 25, 2025 5-8pm
Fridays, November 28 & December 5, 2025 11am-8pm
Thursday, December 4, 2025 5-8pm

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

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 am to 6:00 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

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

Ipswich Illumination

Come to Ipswich Massachusetts as points along the Ipswich River are illuminated!
The Town of Ipswich, Massachusetts, proudly presents 2025 Ipswich Illumination. This year we are celebrating harvest, hearth, & home, and our maritime history, heritage & culture.
11:00 am to 9:30 pm

Saturday, November 22

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

Flying Horse Outdoor Sculpture Exhibit at Pingree School

Pingree School in Hmailton Massachusetts hosts their annual Flying Horse Outdoor Sculpture exhibit each Fall. Sculpture: Phoenix by Robin Tost.
Pingree School hosts the 16th annual Flying Horse Outdoor Sculpture Exhibit on their campus in South Hamilton, Massachusetts .
8:00 am to 6:00 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

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

Family Open House: Nature's Gifts

Use what nature has to offer tomake toys at the Joppa Flats Education Center!
Nature provides special gifts year round from beautiful butterlies to emerging snowdrops in early spring. In this drop-in family program, visitors will meet some "treasures from the ocean" including live beach creatures, seashells from around the world and more.
10:00 am to 3:00 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

SeaFestival of Trees in Salisbury

The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 8:00 pm

SeaFestival of Trees in Salisbury | Saturdays

Experience the joy and excitement of Salisbury’s most popular holiday tradition with glittering trees, indoor ice skating, Santa visits and more,
The Seacoast’s most magical holiday tradition is back! The 13th Annual SeaFestival of Trees opens Saturday, November 22 at the Blue Ocean Event Center in Salisbury, transforming the oceanfront venue into a sparkling winter wonderland of more than 145 themed trees, a giant sand sculpture, Santa’s...
11:00 am to 8:00 pm

Sunday, November 23

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
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