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. 

Entries will be judged on:

  • For the degree of difficulty and creativity
  • Neatness
  • Originality
  • Uses of edible confections and decorations
  • Workmanship
  • Points will be taken away for use of plastics. However, you may use a limited amount

Rules and Guidelines

  1. The contest is open to everyone.
  2. Contestants may submit entries either individually, or as a group. More than one entry may be submitted.
  3. All entries must be made entirely of gingerbread and decorated with candy or other edible embellishments. Anything that appears on the house must be edible. Contestants may decorate their entry with non‑edible figures, material, etc. However, these embellishments may not be connected to the house in any way. Everything that appears on or is connected to the house must be edible.
  4. The gingerbread house submitted may take any shape, form or size. Creativity is encouraged and contestants should model their entries on places or things, real or imaginary, basic or elaborate.
  5. Each entry must be submitted on a cardboard, wooden or plastic base. There is no standard size or shape for the bases although it must be larger than the entry.
    • Entries must be dropped off at Sawyer Free Library Children’s Room, second floor, from Saturday, December 6th to Friday, December 12th. (Library is open: Monday – Wednesday – 8AM to 6PM; Thursday, 10AM to 7PM; Friday and Saturday – 10AM to 5PM)
  6. Judging will occur prior to the start of the Middle Street Walk which begins at 10:00AM on Saturday, December 13th. Entries need to be picked up as soon as possible after the contest.
    Entries are not assured of safety while at Sawyer Free Library.
  7. Prize ribbons will be awarded in numerous categories as stated on the entry form. A special “Best of Show” award plate will be awarded. Please make sure you enter your contact information!

Entry Forms will be available at Sawyer Free Library December 6th-12th. Please be sure to fill out and place it - name down - next to your entry.

When: 
Saturday, December 13, 2025 10am - 3pm
Phone: 
978.281.0639
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

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...
7:00 am to 9:00 pm

Kidleidoscope at Breakheart Reservation

Kidleidoscope is a program designed for preschoolers at Breakheart Reservation in Saugus Massachusetts
Come join our park interpreter for a story time and nature walk! Complete a small craft and explore the woods! Walks are gently paced and approximately 1 mile, though not accessible for strollers. Appropriate for families with children 3-5 years old. Meet at the Visitor Center.
10:30 am to 11:30 am

Fearless | The Taylor Swift Experience

Fearless Taylor Swift Experience at the Sea at Blue Ocean Music Hall in Salisbury MA
Bring your Swifties to Fearless | The Taylor Swift Experience in Salisbury for Fearless | The Taylor Swift Experience—a high-energy, family-friendly tribute that celebrates the music so many kids (and adults) love.
8:00 pm to 10:00 pm

Saturday, February 14

Valentine's Day

12:00 am to 11:59 pm

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...
7:00 am to 9:00 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

The Merrimack River Eagle Festival

Come celebrate the return of the Eagles to the Merrimack Estuary! Photo: Eagle on Ice by Bill O'Connor
When winter returns to the lower Merrimack Valley, so do Bald Eagles and Snowy Owls and other exciting winter wildlife. Every year Mass Audubon hosts a grand event marking their return.  Come to Newburyport on Saturday, February 14, 2026, for a full day of fun indoor and outdoor activities that...
9:00 am to 4:00 pm

LEGO World: Wonderealms

Drop in at LEGO World: Wonderrealms at Wenham Museum in Wenham Massachusetts
This all-new experience invites visitors to explore an extraordinary LEGO world where creativity knows no bounds. From enchanted forests and futuristic skylines to pirate coves and steam-powered frontiers, each realm is packed with intricate details, playful surprises, and clever touches you won’t...
9:00 am to 4:00 pm

Discover Saturdays at Cape Ann Museum

Discover Saturdays for Families at Cape Ann Museum in Gloucester Massachusetts
Enjoy a FREE guided activity (ages 4+) in the gallery. Learn about Cape Ann’s Granite Industry, try a fun art making activity, and join in gallery tour designed for kids and their caregivers, led by a CAM Educator. Afterwards grab a scavenger hunt to explore the property and enjoy the lawn.
10:00 am to 12:00 pm

CraneOutdoors: The Castle Hill Hike

CraneOutdoors: The Castle Hill Hike at the Crane Estate in Ipswich Massachusetts
Come explore the lesser-visited corners of Castle Hill and its surroundings with us this season. This hike is a CraneOutdoors guide favorite because it’s got a little bit of all the things that make the Crane Estate such a special place…
10:00 am to 12:00 pm

Quarry Quest Treasure Hunt

Kids will enjoy this treasure hunt at the Halibut Point State Park and Quarry in Rockport Massachusetts
Enjoy an outdoor treasure hunt at one of Massachusetts most beautiful locations during February Vacation! Halibut Point State Park invites kids and families to follow clues then unscramble to find a treasure box!
10:00 am to 2:00 pm

StoryWalk at Halibut Point

StoryWalk®! Nest Robin Built, by Denise Fleming - a self guided reading tour at Halibut Point in Rockport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! StoryWalk®! Nest Robin Built, by Denise Fleming. Self-guided reading pages posted along a lovely Park trail near the visitor center. Connect with nature and each other while enjoying the...
10:00 am to 2:00 pm

February Vacation at MIT Museum

Kids will have a blast at the MIT Museum in Cambridge Massachusetts during February Vacation Week!
Come on your own, with friends, or bring the whole family to the museum for a special week of programming. The museum has a number of activities planned for the week of February 14-22, including extended Maker Hub and Learning Lab hours, tours, gallery cart demos and family workshops. With the...
Where: MIT Museum
10:00 am to 5:00 pm