House Decorating Contest

Sunday, December 20, 2020

1st Place Winner
2nd Place Winner
3rd Place Winner
Winner for "Best use of Lights"
Winner for "Kids Creation"
Winner for "Prettiest Decorated Doorway"


In 1953, the Pinewood Women's Club began an annual tradition in celebration of the holiday season that would last for over a decade. The annual house decoration contest, which took place each December, was an opportunity for members to show their holiday spirit and bring some winter-wow to our community.  


In a year that has been challenging for so many, the PLA Historical Committee is proud to bring this event back to our community and brighten things up around the lake during December. So, get out your big blow-up decorations, classic holiday wreaths, and utility-bill-busting lights and join us in bringing some holiday cheer to Pinewood. 


When: Sunday, December 20 


How to Participate:  

  • Enter your home - Participation is free and open to all PLA members. See below for details.  


  • Be a judge - we're looking for 1-2 additional members to serve as a judge for this event. Judges will travel to each home to view each home and award prizes.   

  • Contribute a prize - prizes are being secured and will be awarded to each winner. However, if you are a local business operator or craftsman, and would like to donate an item to be awarded, please let us know.  

Contest Information

  • Participation is open to all PLA members. Members who live outside of Trumbull may be judged via photo or video, which can be submitted at any point prior to the deadline.  

  • Entry is free, no cost or fees apply. As part of this event, we’ll be collecting non-perishable food items to donate to a local food pantry. 

  • Judges are not eligible to win.  

  • Applications must be accepted by 11:59 pm on Friday, December 18, 2020. They may be submitted via the online form or at  

  • Contest is limited to what can be seen from the street side of the house at night, including decorations in windows that are visible from the exterior. 

  • Judging will take place on Sunday, December 20, 2020. 

  • Please have your decorations on by 5pm.  

  • Participants agree to have their name and a photo of their decorated residence exterior posted on the PLA website (member portal only) and in the Partyline.  

  • Winners will be announced via PLA eNotice and mentioned in the Partyline.  


Prize Categories:


Prizes will be awarded for:  

  • First place - this will be awarded to the best overall entry. 

  • “Prettiest Decorated Doorway” – this category is a nod to the original contest category. The winner will showcase a classic holiday look and feel, throwing back to holidays past. 

  • Kids Creation – make this a family affair! The winner of this category will get the kids involved (e.g. showcase a children’s theme, incorporate children in the planning and execution, highlight decorations/displays created by the kiddos themselves, etc.)   

  • Best use of lights - this house would make Clark Griswold cheer with joy! The winner of this category will use lights in a creative and impactful way.

Note, by nature of this event, we'll be able to maintain proper social distancing. Additional measures will be put in place to ensure we are adhering to all government mandates related to COVID-19.