The Ultimate Connecticut Would You Rather Questions for Locals

I love Connecticut. I know that’s not always the cool thing to admit out loud, but I really do. I love the weird pride we have, the constant arguing about pizza, the way half the state pretends it’s not New England and the other half pretends it’s not New York. I love the landmarks, the history, the random roadside nonsense, and the fact that no matter where you are, someone nearby has a very strong opinion about something.

Get our free mobile app

I also love Would You Rather questions. I love how quickly they turn friendly conversations into arguments, how they reveal who people really are under pressure, and how nobody is ever satisfied with the options. So naturally, I thought: why not combine two of my favorite things? Connecticut… and chaos.

So here we go. A very Connecticut edition of Would You Rather, inspired by the places, people, history, food, and lore that make this state what it is.

Would you rather defend New Haven pizza to a room full of New Yorkers, or explain Hartford’s layout to someone who’s already angry?

Would you rather get stuck behind a tractor on a back road in Litchfield County, or sit in I-95 traffic forever knowing you’re only five exits from home?

Would you rather live in Mystic during peak tourist season, or try to park in West Hartford Center on a Saturday night?

Would you rather fight a goose on the New Haven Green, or make eye contact with a deer on the Merritt Parkway and know it’s about to make a bad decision?

Would you rather only eat Connecticut-style lobster rolls forever, or be forced to admit the warm butter version is also good?

Read More: Everything You Need to Know About the I-95 Morning Show After Dark Coming to Newtown 

Would you rather give a guided tour of the Mark Twain House with no prep, or explain to out-of-staters why there are casinos in the woods?

Would you rather be haunted by a Revolutionary War ghost from Old Wethersfield, or trapped overnight in an abandoned wing of the Brass Mill Center in Waterbury?

Would you rather attend every single town hall meeting in your town, or argue about property taxes with your neighbor until one of you moves?

Would you rather survive a winter storm with Eversource updates every 12 hours, or lose power with zero communication and vibes only?

Would you rather admit you secretly enjoy the Merritt Parkway, or pretend Route 8 isn’t slowly stealing years off your life?

Would you rather only drink coffee from a local CT café forever, or be banned from mentioning Dunkin’ ever again?

Would you rather explain Connecticut to someone who thinks it’s just “between New York and Boston,” or listen to someone call it “basically New Jersey”?

This is what I love about Connecticut. It’s small, but it’s packed. History, attitude, scenery, chaos, pride, and just enough dysfunction to keep things interesting. And honestly, Would You Rather feels like the perfect way to celebrate it���������������because no matter what choice you make, someone from another town is going to tell you you’re wrong.