All Ages

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

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

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: 

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: 

Harvest Market at Appleton Farms

Harvest Farmer's Market at Appleton Farms in Ipswich Massachusetts. Fresh Local Fall Harvest Produce and other foods

Join us in a celebration of the Harvest season at our annual Harvest Market! Our Harvest Market features a bounty of Appleton’s organic produce accompanied by other local edibles & gifts from area artisans, crafters, and producers of fine foods. The Appleton culinary team will also have sweet & savory treats available for purchase to keep you fueled while you shop!

When: 
Saturday, November 1, 2025 12-4pm
Location: 

Salem Witches' Magic Circle

Join the Witches of Salem on the Salem Common to celebrate the Magic Circle - a Halloween tradition!

Halloween is the night when the veil between the world of the living and the world of the dead thins and magicla things happen!  Join Christian Day and Brian Cain with drumming by the Dragon Ritual Drummers as Witches from around the globe gather for the sacred and magical ritual of Halloween! This event is free and open to all who wish to attend with an open heart and a love for their dead. There is also no limit on the number of participants.

When: 
Friday, October 31, 2025 5-8pm
Location: 

Wicked Wednesdays at the Phillips House

Wicked Wednesdays at Historic New England's Phillips House in Salem Massachsuetts part of Haunted Happenings

Join Historic New England for Wicked Wednesdays! Get wicked at Phillips House as part of Haunted Happenings family-friendly events. Ticket includes historic games, fall crafts, and a family- themed tour of the house. Coxstumes Welcome! This is a drop-in event. Tours are offered every half-hour. Last tour departs at 5:00 p.m.

When: 
Wednesday, October 29, 2025 3-6pm
Location: 

The Open Door Autumn Breakfast

The Open Door Autumn Breakfast is a fundraiser that helps families in need on the North Shore

Cruiseport Gloucester and The Open Door invite you to a celebration of community spirit! Each year, The Open Door Autumn Breakfast kicks off the holiday giving season and raises funds for Holiday Meal Baskets (and beyond). Each basket provides local people with all the ingredients they will need to make a special meal, and Holiday Baskets are available for BOTH Thanksgiving and the winter holidays. LIMITED SPOTS AVAILABLE, purchase tickets in advance to guarantee your spot.

When: 
Wednesday, October 22, 2025 7:30-9am
Location: 

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Appleton Farms offers great farm-based Vacation Week Programs for kids ages 5-11

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

Saturday, November 15

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

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

Waldorf Enchanted Fair - Moraine Farm

Enchanted Fair at Waldorf School at Moraine Farm. Beverly MA
The school campus will be transformed into the magical Enchanted Fair! Come join us for family-friendly games, crafts, music, fireside stories, food, and shopping. All activities, crafts, and food will be purchased using tickets. Pre-order your fair tickets today! Tickets will also be available for...
10:00 am to 4:00 pm

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.
1:00 pm to 3:00 pm

Low-Sensory Play at North Shore Children's Museum

Low-Sensory Play at NorthShore Children's Museum in Peabody Massachusetts
Join us for a low-sensory play session. For some children, visiting places like NSCM can be over-stimulating. This special play session will have reduced noise, crowds, and stimulation. While medical diagnosis is not required, we encourage that these limited tickets be used for families with a...
2:00 pm to 4:00 pm

Sunday, November 16

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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