With its parades, pumpkins, and trunk or treat events scattered around the state, Connecticut owns Halloween! But, how is your little ghost and goblin supposed to find the best neighborhood to go trick-or-treating in on the big night? We have scoured the region looking for the most boo-rific blocks around. So, grab an old pillowcase along with this list of tried and true neighborhood favorites, and head out for a night on the town. Remember: You get first pick of candy for doing all the legwork.
Best Trick-or-Treat Neighborhoods in Fairfield County
Trick-or-Treating along Ponus in Norwalk is always full of treats!
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!)
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.
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!
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?
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.
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.
Main Street & New Street—Ridgefield
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—Stamford
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)—Stamford
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!
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—Westport
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.
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!
Best Trick-or-Treat Neighborhoods in Litchfield County
Head to Meadow Street in Litchfield for a little Halloween fun!
Trunk or Treat on the Town Green—New Milford
A "safe alternative" to trick or treating. Instead of trick or treating in your neighborhood people are asked to register their vehicles, decorate them, and then park around the town green on Halloween night from 5:30-7:30. You can pass out candy as children "trunk or treat" from car to car.
The Town of Litchfield is one of the larger villages in Litchfield County with a beautiful green lined by fine restaurants, galleries and shops. The local school is right down the road and homes are quite close to one another, meaning lots of candy! In the past, thousands have gathered on Meadow Street while the firemen and police closed off the street to traffic. However, residents became overwhelmed and many shutter their homes for the night. That being said, it's still a nice place to wander on Halloween night but it might be better to stay closer to home if possible.
Roxbury is a darling historic village and the homeowners take Halloween seriously. On South Street you'll find creatively decorated homes as well as loads of children doing tricks for treats (or not). Some homeowners even put on their own mini haunted houses.
For the Norman Rockwell trick or treating experience head to quaint Kent. Businesses on Main Street get into the spirit with decorations and handing out candy. Children then walk over to Elizabeth Street for trick or treating from home to home. Don't miss the Thriller Flash Mob at 7pm on Main Street!
Best Trick-or-Treat Neighborhoods around New Haven
Trick-or-Treaters line the streets of this New Haven neighborhood. Image courtesy of Chris Randal via ilovenewhaven.com
Morris Cove—New Haven
Several Facebook readers gave us the inside scoop that the Morris Cove neighborhood of New Haven is THE place to be on Halloween Night! This parade takes over the street - and everyone gets involved!
North Main Street—Wallingford
Police are on the street to direct around a thousand trick-or-treaters safely around the North Main Street neighborhood in Wallingford. Local residents have even started a candy drive for families who live along North Main to help them with the expense of all that candy!
Tons of kids meander through secluded closed loops of this small neighborhood. Residences provide the ambiance with great Halloween lights and displays.
You will need to find alternate parking if you want to trick or treat along Quinn Street in Naugatuck. Local homeowners are prepared to hand out around a thousand pieces of candy every year - and they still run out!
Best Trick-or-Treat Neighborhoods in Hartford County
Cannons shoot ghost and treats into the crowd at the Collinsville Halloween Parade. Image courtesy of the Collinsville Art Party
OK, so the Collinsville Halloween Parade doesn’t actually take place on Halloween. But, its not so often that a small Connecticut town event appears on a list of the Best Trick or Treating Towns in the entire country! Not only is the Collinsville Halloween Parade on The Daily Meal’s list, but they are number 2! This event usually kicks off the Saturday before Halloween. The resident ghost - Boosolini - kicks off the event and cannons shoot treats at the crowds.
Trick-Or-Treat Safety Zone—New Britain
For the seventh year, New Britain invites thousands of children to trick-or-treat in the downtown area. There are over 30 candy distribution spots that keep the treats flowing from 5:00-7:00.
Downtown Willimantic comes alive on Halloween night! From Church Street to High Street, the neighborhood will be closed to traffic to allow over 30 merchants to hand out treats. Additionally there is a trunk-or-treat event and a jack-o-lantern competition.
Best Trick-or-Treat Neighborhoods in Eastern Connecticut
Old Mystick Village is the perfect place to get your treats!
Old Mystik Village—Mystic
It doesn’t get much more quintessentially Connecticut than trick-or-treating through Olde Mistick Village on Halloween night. Trick-or-Treaters will also have the privilege of choosing which shoppe is decorated the spookiest!
You know how have arrived when “Best Trick-Or-Treating Neighborhood” is included in your real estate listing. Well, that is JUST the case for the folks who live along Bartlett Drive.
Cover image courtesy of Chris Randal via ilovenewhaven.com. Unless indicated, all other photos are courtesy of Mommy Poppins.
Originally published October 1, 2017