Five ways to do Halloween around Fairfield County without voluntarily being chased through a field
Halloween has become a strangely high-pressure holiday. Somewhere along the way, eating candy and putting on a costume stopped being enough. Now there are haunted forests, extreme haunted houses and corn mazes specifically designed to make you question every decision that led you there. Respectfully, some of us would just like a pumpkin.
Luckily, October around Fairfield County has plenty of ways to participate without spending the evening wondering why you paid money to be terrified. Here are five that are festive, charming and appropriately spooky.
PAINT THE TOWN | WESTPORT
One of Westport’s sweetest Halloween traditions turns downtown itself into the decoration.
On Saturday, October 24, kids take over storefront windows for the annual Halloween Window Painting Contest.
Young artists get their own section of glass to transform with ghosts, pumpkins, witches and whatever else qualifies as spooky in their world. The best part comes afterward. The paintings stay up through Halloween, which means a regular Main Street walk turns into one giant, wonderfully imperfect seasonal gallery. Even if nobody in your house is competing, make a Saturday out of it. Grab coffee, walk around while everyone is painting and come back later to inspect the finished work.
Professional window displays are lovely. A nine-year-old being handed paint and three square feet of glass is better.
HAVE A PROPER PUMPKIN SATURDAY | WILTON
The Great Wilton Pumpkin Fest is fall in its most New England form.
There are pumpkins, cider, donuts, lawn games, a scavenger hunt and pumpkin decorating, all set around the Wilton Historical Society’s historic property. Then there are the things you did not necessarily expect to become fascinated by, like open-hearth cooking and blacksmithing demonstrations. This is the kind of afternoon where kids can decorate a pumpkin while the adults stand nearby saying, “Wait, how are they actually making that?”
Pick out a pumpkin before you leave and bring it home for the front step. October assignment completed.
LET ELM STREET HANDLE TRICK-OR-TREATING | NEW CANAAN
On Sunday, October 25, Elm Street belongs to the costumed population.
New Canaan’s Halloween Block Party closes the street to traffic while local businesses hand out candy, music plays and families take over downtown.
The real appeal is how easy the whole thing feels. Little kids can wander. Strollers have room. Dogs inevitably arrive in costumes. Parents can actually stop and talk without simultaneously monitoring a toddler and an SUV. Parents and grandparents are encouraged to dress up too.
Whether you choose to take them up on that invitation is between you and the costume aisle.
WATCH HOCUS POCUS WITH BETTER SNACKS | FAIRFIELD
There are movies we watch because they are excellent.
And then there are movies we watch because October arrived and apparently the Sanderson sisters now have custody of us. On October 28, SHU Community Theatre is turning its screening of Hocus Pocus into a Taste-A-Long experience, with Halloween-inspired bites timed to moments in the movie. It is nostalgic, festive and considerably easier than hosting your own Halloween movie night.
Gather the people who can quote the movie without prompting and allow someone else to handle the snacks. That is our preferred level of seasonal hosting.
SAVE THE WEIRD FOR FRIDAY NIGHT | FAIRFIELD
Then there is Halloween for grown-ups.
On October 30, The Rocky Horror Picture Show gets the full live-show treatment at SHU Community Theatre. If you have somehow made it this far without seeing Rocky Horror with an audience, understand that this is not a sit-quietly-and-watch-the-movie situation.
The chaos is part of it. Costumes are encouraged. Participation is expected. Being slightly overdressed is nearly impossible. For one October night, weird is the dress code.
There.
Halloween spirit achieved.
Nobody had to run through a cornfield.