Written by Gia Miller and Kayla Schmidt
Jessica is a real estate agent with Rand Realty and a “community hype girl” who strongly believes that communities help people build meaningful connections and increase home values. She takes a lot of pride in teaching people about sustainable choices that can help them save money and make better choices.
Why did you want to be a judge?
I really patronize the majority of small businesses in our area, and I want to see them succeed and do well. Plus, I love anything that’s helping people make better choices, like who to visit and support.
What stood out to you during the judging process?
The other judges and the community are so passionate about small businesses.
Did you take bribes? Be honest…
Nope; I’m not bribable. I’m too opinionated to be bribed.
What was your judging philosophy?
I think it’s really important that you’re in places that make you feel good. So my goal was to highlight businesses that really gather people. Because if people want to hang out there, they must be doing great things.
Who was the most opinionated judge in your opinion?
You mean, aside from me (laughs)? I would say probably Vanessa. She really got in there.
What’s harder: keeping the winners a secret or keeping your personal opinions to yourself?
Keeping it a secret. I’m so excited, and I wish I could tell everybody right now. I want them to know they were talked about in a really positive way. In a world of negativity, talking about awesomeness is a privilege.
Did you burn your notes after judging?
No. Was I supposed to?
You’re going on the judge circuit. What type of contest would you rather judge?
Best dog costume or most delicious vegan chili?
I’m going with the most delicious vegan chili, because I always like what unique flavors people come up with to replace or mimic meat. I think it’s very creative and interesting.
Most dramatic eye roll or worst parallel parking attempt?
Oh my gosh, the worst parallel parking attempt. And let me tell you, there are some great spots in Bedford if you want to watch people struggle with parallel parking. I have literally laughed out loud before.
Funniest kid dressed up as Charlie Chaplin or most aerodynamic wheel of cheese to roll down a hill?
Oh, interesting. I’ll choose the cheese because I’m now fascinated by it; I’ll be thinking about that after this interview.
Funniest impersonation of a cat throwing up or best folded fitted sheet?
Best folded fitted sheet, and, also, can the winner teach me how? Because it doesn’t matter how many videos I watch, I cannot properly fold a fitted sheet.
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).
