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Navigating best 3 Westport Halloween havens

Graphic by Lily Rimm ’25
The annual celebration of Halloween can be navigated with advice on specific Westport hot-spots and uniquely decorated streets.

The month of wearing spooky costumes, decorating houses with cobwebs and handing out candy is finally here. While most teenagers today become engrossed with the idea of Halloween parties, they’re missing the most important part of October’s delight: trick-or-treating. 

A truly successful Halloween adventure involves a strategy of where to find sugar satisfaction. Most importantly, an atmosphere that provides both thrill and festivity is vital. As an avid trick-or-treater, I have collected data on the best Westport spots to hit over the past two years. While there are many options for participating in the celebration, here are some specific neighborhoods that are known to take great pride in taking trick-or-treating to the next level.

  1. Compo Beach
Lily Rimm ’25

The Compo Beach area defines a close knit neighborhood. The houses are densely packed, and the narrow streets limit car traffic. The residents are known to hand out deluxe, full sized candy bars on Halloween night, and several houses on the block decorate their houses to the max. This is an ideal setting for both children and teenagers to run freely, collecting treats and being part of a collective spookily sweet energy. Some might view Compo as chaotic on Halloween night, but others are excited by the buzz and liveliness. All of this comes with salty air and great views of the Long Island Sound.

2. Gault

Lily Rimm ’25

Gault Avenue, about a five minute drive from the beach, is a picture-perfect fall enclave. Gault Avenue’s homeowners famously take pride in their annual decorations for Halloween, and therefore create a festive and cheerful atmosphere. There are just enough houses but not too much walking. The side streets off Gault lead into cul de sacs, which provide for a smaller and more enclosed Halloween experience. Rest assured, due to the popularity of the area, the police maintain a presence to provide a riveting, yet safe Halloween.

3. Gorham

Another consideration for your trick-or-treating pleasure is Gorham Avenue. Gorham is a long, quiet and wide street, which seems to go on forever. It’s possible this one street could satisfy even the most zealous trick-or-treater. It is close in proximity to downtown, which provides the option of  trick-or-treating at Main Street shops as well. Gorham’s houses are not too far apart, making it especially convenient for younger trick-or-treaters. 

A truly successful Halloween adventure involves a strategy of where to find sugar satisfaction.

— Lily Rimm '25

Halloween truly provides a unique chance to connect with one’s community, and relish in the simple pleasure of a well earned treat. Regardless of what neighborhood you choose, may your Halloween be filled with just the right combination of tricks and treats. 

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