Written by Gia Miller and Kayla Schmidt
Jennifer, of Northern Westchester Moms, is incredibly passionate about local businesses. She spends her days supporting local businesses on her website and social media pages, doing her part to help each one succeed.
Why did you choose to return as a judge?
The first experience was so magical. To see local businesses get a highlight and a shout-out, and to see those purple stickers all over town, has been really amazing, inspiring and exciting, so I couldn’t wait to do it again.
What stood out to you during the judging process this year?
It was actually a lot harder to pick people this year because we had such a good first round. And it was a little trickier because I pushed myself to think about different people we could highlight and be more thoughtful with my responses.
Did you take bribes? Be honest…
No way, Jose! Never! I’m way too honest.
What’s harder for you, keeping the winners a secret or keeping your personal opinions to yourself?
Oh, keeping my personal opinions to myself!
If you could sum up the experience in one word or phrase, what would it be?
So much fun! It is so much fun to chat about our community and our local businesses. It’s magical; it reminds me why I live here. And let’s be honest, it’s not always easy to live here. Sometimes it’s expensive, and there’s a lot going on. But it’s also really magical.
You’re going on the judge circuit. What type of contest would you rather judge?
Best dog costume or most delicious vegan chili?
Most delicious vegan chili, because I’m a vegetarian and I love vegan food.
Ugliest ugly sweater or preschool talent show?
Preschool talent show. I love little people; they’re the most adorable little things. They’re brutally honest, and they’re just so stinking cute because they’re not jaded by the world yet.
Best creative cocktail or most exquisite hula dance?
The most exquisite hula dance because I don’t drink alcohol.
Most creative excuse for being late, or best secret handshake?
My son and I have a secret handshake. So I do love a secret handshake.
Funniest kid dressed up as Charlie Chaplin, or most aerodynamic wheel of cheese to roll down a hill?
Well, I love cheese, but the first one would just be adorable, right? It’d be just so stinking cute.
Funniest impersonation of a cat throwing up or best folded fitted sheet?
Best folded fitted sheet because that’s the hardest thing in the world to do. But I can do it if I really concentrate.
Most unusual pet in a bathing suit or beatboxing championship?
Beatboxing. People who can beatbox are my heroes. I don’t know how they can make their mouths do all those sounds, but it’s incredible.
This article was published in the January/February 2026 edition of Connect to Northern Westchester.
To view all 2026 Connect to the Best winners, click here.
Gia Miller is an award-winning journalist and the editor-in-chief/co-publisher of Connect to Northern Westchester. She has a magazine journalism degree (yes, that's a real thing) from the University of Georgia and has written for countless national publications, ranging from SELF to The Washington Post. Gia desperately wishes schools still taught grammar. Also, she wants everyone to know they can delete the word "that" from about 90% of their sentences, and there's no such thing as "first annual." When she's not running her media empire, Gia enjoys spending quality time with friends and family, laughing at her crazy dog and listening to a good podcast. She thanks multiple alarms, fermented grapes and her amazing husband for helping her get through each day. Her love languages are food and humor.
Kayla Schmidt
Kayla Schmidt is a sophomore at Horace Greeley High School. She is part of the newspaper and the SADD club, and she is also the co-manager of the track team. In her free time, Kayla enjoys spending time with her friends, family, and dogs, along with reading (preferably on the beach).
