Jimmy’s Soft Serve Gets Into High Gear Ahead of Wine & Food Fest

There are two kinds of people in this world: fools, and those who look at the dessert menu first so they know how much room to save beforehand. In that same culinary spirit, before we open the gates of this summer’s Wine & Food Festival we thought you deserved a sneak peek at some of the sweet treats that’ll be on hand for you to close out your dining experience at our Burger and Beer Bash on Thursday, June 7. (Or hey, just go straight for the desserts and gorge yourself. This, too, is a valid option.)

First up, we reached out to Jimmy Annicharico, founder and namesake of Jimmy’s Soft Serve, a pair of Westchester’s best-loved ice cream trucks that have been serving up cones and bowls, shakes and floats, shaved ice and sundaes for a full decade now.


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What are you most looking forward to about participating in the Wine & Food Festival and specifically the big Burger & Beer Bash?

I’m most looking forward to seeing some of the people in the business I’ve met along the way. Those we’ve collaborated with who I can now call friends and catch up with while there, and have a great time while also showing off our business and what we are about to the people Burger Blast who might not be familiar with my truck.


You’re currently celebrating the 10th anniversary of Jimmy’s Soft Serve. What can you tell us about maintaining staying power in an industry where making it past twelve months is generally considered an accomplishment?

Yes we are excited to announce this is our 10-year anniversary! We have great support from our customers who are honestly the greatest and without them I wouldn’t be here! That has help us maintain a presence year after year and given me that spark to think I’m doing something right and keeps me going. Customer service is my number one thing I pride myself on. I live by the old school way that the customer is always right, which is something that I see fading away from businesses these days and it seems like it’s more of a burden for some to make them happy in a world where one bad experience can lose ONE great customer!

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It’s always good to see local businesses opening second locations. What were some of the challenges with adding a second food truck to the Jimmy’s roster?

I pondered expanding for several years and I finally decided to take the leap! (gulp) We are a private event ice cream truck for corporate, birthdays, A-list celebrities, weddings, etc., so we were getting a lot of calls for events while the other original truck was already booked. I never wanted to turn away customers, so that’s where the second truck came into play. That being said, with two trucks comes two headaches at times, and trying to manage employees and coordinating the following days’ events accordingly … I’m not gonna lie, it’s hard work! It’s not as easy as people from the outside looking in think. Owning your business has pros and cons; it’s not all ‘rainbows and unicorns’ which is a motto we use here. You have to be willing to put the loooong hours and expect the unexpected, because just when you think everything is going great it can quickly escalate. You have to learn to keep “cool” and not cry over spilled milk.

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Jimmy’s has also been recognized for its quality with several Best of Westchester nominations. What makes your soft serve experience unique to our area?

Being nominated for Best of Westchester was a great feeling honestly, and to be alongside some of the best in the business is an honor in it self. Along with Best Food Truck, one of the categories we were nominated for was Best Milk Shake, which I like to think is one of my best items. To get the nomination was pretty sweet.

We’re not your average ice cream truck. We like to get creative here and keep people guessing. I also have a great family support system and I’m lucky to have them, the whole family pitches in when necessary to which I say thank you! Also, whether it’s letting a little child come in to the truck and let them make his or her own ice cream at their birthday party, or having a corporate company treat their employees to a ice cream party, or a bride and groom coming in to take photos for their wedding album to last a lifetime, it’s all about the Jimmy’s Soft Serve experience! We’ve done parties from 6 to 6,000, and my goal is to have each one leave with smile. It doesn’t cost money to smile and I have an unlimited supply here at Jimmy’s. 



Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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