10 Ways to Celebrate Halloween | Newtown Moms

The second half of October is filled with Halloween related events and we have them all listed on our calendar. Below you’ll find a mix of ten ideas that will get you in the Halloween spirit. Enjoy!


10. Over the course of the next two weeks, there are tons of Trunk or Treats scheduled. Our calendar includes all the details for the following:

  • 10/20: 9th Annual Trick or Trunk, Masuk High School, Monroe
  • 10/25: St. Joseph’s Catholic Academy Trunk or Treat, Brookfield
  • 10/25: Stew Leonard’s Trunk or Treat, Danbury
  • 10/26: Trunk or Treat, Brookfield Volunteer Fire Department, Brookfield
  • 10/27: St. Paul’s Church Trunk or Treat, Brookfield
  • 10/31: Halloween Trunk or Treat, New Milford Green, New Milford


9. Plan a night to go on a Haunted Hayride at Legends of Fear in Shelton. Fun for adults & older children, this annual event runs the last weekend in September through the first weekend in November. For tickets, head to the website. 


8. The Enchanted Castle is back at the Burr Homestead in Fairfield! Run by the Junior League of Eastern Fairfield County, the Castle is a family friendly event that features Cinderella, The Little Mermaid, Pirates, Beauty & the Beast, and Aladdin. Perfect for kids ages 2 – 10, but fun for the whole family.


7. Take your child(ren) to a Music Together Halloween Singalong. There are several opportunities throughout the next two weeks listed on our calendar, including two FREE events at local senior living facilities. Costumes are encouraged and they’ll even be a photo booth for snapping a cute picture of your child. This event is for kids up to age


6. If you have the time, take the short trip to Cortlandt Manor to The Great Jack O’Lantern Blaze. Walk through an illuminated display of more than 7,000 jack’o’lanterns. 

5. If you’re looking for a scare this October, Harrybrooke Park’s Haunted Trail will definitely take care of that. This event is put on by a number of non-for-profits in New Milford with proceeds directly benefiting these organizations.


4. Head to City Center Danbury on Saturday 10/26 to participate in Halloween on the Green. Event includes a costume parade, costume contest, goodie bags, food trucks and more.


3. Bethel is holding their annual Trick or Treat Street on Saturday 10/26 starting at noon. Starting at the Municipal Center, families can enjoy music, games, and a haunted house. Afterwards take part in the Candy Crawl through downtown Bethel.


2. The 9th Annual Sandy Hook Halloween Walk is in the process of being planned for Saturday 10/26 from 11AM – 2PM. Trick or treat early at the business in Sandy Hook Village. Tickets for this kid-friendly event will be available online soon. Stay tuned here for updates.


And last, but certainly not least is trick or treating on Main Street in Newtown. An estimated 3,000 people trick or treat on Main Street each year and this is one event in town that does not disappoint. Many of the homes along Main Street go all out with decorations and it is truly an experience for any kid or grown-up.

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