Best Places to Trick-or-Treat in Connecticut - Fairfield County

Lake Drive—Darien

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—Darien

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

 
There are some super trick-or-treat neighborhoods in Connecticut worth suiting up for. Photo by Ben Wildeboer, via Flickr (CC BY-NC-ND 2.0)

Jackman Ave—Fairfield 

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—Greenwich  

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—Greenwich 

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. 

Ponus Ave—Norwalk

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

On October 30th, the whole town will come 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. 

 
There are so many Connecticut neighborhoods that embrace Halloween, and make the trick-or-treat experience special. Photo courtesy of Mommypoppins.com

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! 

Hilltop Circle—Trumbull

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.

 
Westport offers one of the best trick-or-treat neighborhoods in Connecticut! Photo courtesy of the Westport Downtown Association

Compo Beach Area—Westport

Compo Beach offers a trifecta: short driveways (check!), flat terrain (check!), and 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—Westport

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 pm. I have heard that the crowds can be a little overwhelming for the toddler crowd, but it is great for older kids! 

Griswold Avenue—Bethel

Come on down to Trick or Treat Street in the Historic District. The Bethel Chamber of Commerce invites you to trick-or-treat at local businesses from 1-3 pm. There will be a costume contest, a DJ playing live music, and tons of tasty treats.

Trick-or-Treat with the Horses—Wilton

 
Trick-or-treat at the stables in Wilton, CT this Halloween. Photo courtesy of Rising Starr Horse Rescue

Here's something different. Put on your costume and trick-or-treat equestrian style at Rising Starr Horse Rescue. There will be 32 stalls/horses with treats for you. Suggested donation of $10 for the charity and a unforgettable memory for free!

Best Places to Trick-or-Treat in Connecticut - Litchfield County

Trunk or Treat on the Town Green—New Milford

Instead of trick-or-treating in neighborhoods, volunteers register their vehicles, decorate them, and then park around the town green on Halloween night from 5:30-7:30 pm.  

Meadow Street—Litchfield

The town of Litchfield is one of the larger villages in Litchfield County, with a beautiful green lined by fine restaurants, galleries, and shops. Homes are quite close to one another, meaning lots of candy! In the past, thousands have gathered on Meadow Street while the fire and police services close off the street to traffic.

South Street—Roxbury

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. 

Main Street—Kent

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 to trick-or-treat from house to house. Don't forget to get your glow necklace from the State Trooper. He hands them out on Main Street from 5-7 pm.

Best Places to Trick-or-Treat in Connecticut - New Haven

Trick-or-Treaters enjoy decorations in a New Haven neighborhood. Photo courtesy of Newhavenindependent.org

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 thousands of 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!  

Strathmore Woods—Cheshire

Tons of kids meander through secluded closed loops of this small neighborhood. Residences provide the ambiance with great Halloween lights and displays.

Quinn Street—Naugatuck 

You will need to plan out parking in advance 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!

Trick-or-Treat the Derby Neck Library—Derby

Stop by the Derby Library as you make your way around town. If you come in costume, you will receive a goody bag between 3-5 pm.

Best Places to Trick-or-Treat in Connecticut - Hartford County

Boosolini, the resident ghost, kicks off the popular parade in Collinsville. Photo courtesy of Collinsvillehalloween.com

Collinsville—Canton 

OK, so the Collinsville Halloween Parade actually happens on October 29th, but, it's 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 it is ranked number 2. This event usually occurs the Saturday before Halloween. The resident ghost - Boosolini - kicks off the event and cannons shoot treats at the crowds. 

Annaliese Avenue—Southington

This neighborhood really comes together to have fun on Halloween. It's a busy trick-or-treating street with many decorated home for families to enjoy. There are also many small side streets to trick-or-treat down as well.

Broad Street—Windsor

Downtown Windsor is hopping every year for the Nightmare on Broad Street event. At this massive Halloween event on the green, kids can trick or treat, watch a Halloween movie, take a hay ride and more. The neighborhoods around downtown are hot destinations for trick or treating too, so bring a big bag if you are walking through Elm, Maple or Sycamore.

Best Trick-or-Treat Neighborhoods in Eastern Connecticut

Olde Mistick Village is the perfect place to trick-or-treat! Photo courtesy of Old Mystick Village, via Facebook

Olde Mistick 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. 

Bartlett Drive—Madison

You know you 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. 

Halloween Spook-tacular Trick-or-Treating at the Tanger Outlets—Mashantucket

Kids can trick-or-treat in the outlet from store to store during the day, from 4-7  pm. There will be a magician performing, as well as some fun Halloween music.

Originally published October 2017

Updated October 2022