Trick-Or-Treat Neighborhoods in Fairfield County

Best places for trick or treating in Fairfield County

Trick-or-Treating was a LOT of fun as a kid, but it is arguably more fun as a parent.  Personally, I’ve hit some rough, tantrum filled, patches along the way - empty neighborhoods, houses half mile apart, long driveways, no street lights, speeding cars - I never knew how many things there were to think of when planning your All Hallows Eve! Then, one year we hit trick-or-treating gold!  We found a neighborhood in Fairfield County  that was filled with kids, candy, and plenty of Halloween Spirit.  This got me thinking, what makes a trick -or- treating neighborhood great? 

Over the years,I have concocted the following recipe for a perfect Halloween night : 1 part short driveways, a splash of flat terrains, and a dash of close and decorated houses. This magical potion allows for optimal fun for everyone involved!  Grab an old pillowcase and this list of tried and true neighborhood favorites, and head for the streets. Remember - you get first pick of candy for doing all the legwork. If you are looking to have your little ones practice their "trick-or-treat" before the big day, make sure to check out the Best Places to Trick or Treat in Connecticut this Halloween.

Lake Drive
The Lake Drive/Phillips Lane loop off of Hoyt Street is popular with younger kids. This neighborhood knows how to have some family friendly fun! Wide streets with flat and short driveways make it easy for little ones to navigate (even with a mask on!) 

Elm Street
Not quite a nightmare, Edgerton, Elm, and Fairfield Street off of West Ave. is also good for little kids. Police have been known to shut down the streets in these neighborhoods so the kids can get around safely.

Jackman Ave
This densely settled  neighborhood boasts awesomely decorated houses, short driveways AND a local firehouse that opens up and hands out treats, hot chocolate, and cider. You can’t beat that! 

Orchard Street 
In the Cos Cob section of Greenwich - off of Orchard Street - the trick-or-treating is pretty amazing! The houses are decorated, the candy is flowing. What else can we ask for on All Hallows Eve?  

Maher Ave 
The close knit community along Maher Ave is prime trick-or-treating country. Unlike the sprawling estates in “Backcountry” Greenwich, this neighborhood offers sidewalks and houses that are pretty close together. 

Photo  by Laurie Rein

Ponus Ave 
Grab some friends and hit the streets that wind around Ponus Ave in West Norwalk. The streets in this close knit neighborhood are always a good place to spend your Halloween in Norwalk. 

Main Street & New Street 
The whole town comes out to celebrate in this downtown neighborhood of Ridgefield - and who can blame them. The Connecticut Post has named Ridgefield 2016’s safest town in Southwest Connecticut.  They normally close down the street to allow everyone to safely travel from house to house - most people end up on Main Street. 

Cove & Shippan Neighborhood 
The 06902 earned some bragging rights this year - Hearst Media ranked it the top zip code in the state to go Trick-or-Treating.  Word on the street is there is even a haunted house (in a private residence) located next to the Stamford Yacht Club 

Springdale Neighborhood (Minivale Rd and Bouton St) 

Photo  by Katie Kaplan

I have seen first-hand how serious the Springdale neighborhood takes its Halloween. Packs of families and children invade this “small town” of a neighborhood located in the heart of Stamford. The houses along Minivale and Bouton Street are majorly decorated! 

Hilltop Circle 
This neighborhood is touted for truly embracing the Halloween spirit with amazing decorations.  Of course, those decorations tend to also draw large crowds - so make sure you get their early if you need a parking space.

Compo Beach Area
Short driveways (check!), Flat terrain (check!) Hundreds of sugar crazed children roaming the streets (check!). You can park at the Soundview Lot and work your way through the adorable little streets lining the Sound. 

Gault Avenue
This is THE Trick-or-Treat neighborhood in Westport. Crowds start to arrive as soon as the sun starts setting - so make sure you get there early. Trick-or-Treating ends promptly at 9:00.  I have heard that the crowds can be a little overwhelming for the toddling crowd, but it is great for older kids! 


Cover Photo by Julia Raasch on Unsplash