During the pandemic, 35-year-old Gillian Osnato recognized that more and more people were being drawn to Millerton, NY. Its growing popularity has made the town a true destination. “I thought that every vacation spot needed a charming candy and ice cream store,” Gillian describes. “So, I decided to go for it!”

While working with her father at his store, the T-Shirt Farm, which is also in Millerton, Gillian witnessed the “Millerton Boom” firsthand. This eventually gave the Lakeville, CT, native the inspiration to start a venture of her own. “It actually started as a joke about my dad needing a bigger space to put all the Funko Pops he was ordering and blossomed from there,” she recalls. “He has been self-employed for my whole life (and even longer) so it was natural that I would take inspiration from him.”

Photo by Aly Morrissey.

In March of 2021, Gillian opened Candy-O’s Sweet Shop, which sells candy, ice cream, chocolates, and other goodies. While her education – an undergraduate degree in English Literature – doesn’t necessarily reflect her current path, Gillian explains that she’s worked her way up to management positions in retail since she was a teenager.

“And I have always had a passion for food and the food industry,” she says. “I love how food can bring comfort and nostalgia. I embraced that idea with the candy store. I think that everyone remembers their first experience in a candy store or the candies they ate as a child that still bring that same joy to them as an adult.”

Crafting the store’s brand

This sentiment is quite aptly reflected in the shop’s branding and atmosphere. Paying homage to the 70s rock and roll scene, the name Candy-O’s is a play on The Cars album title and song “Candy-O,” while also tying in the “O” in Gillian’s last name.

The overall feel of the store is also very retro and old-fashioned, with the nostalgic sentiment especially present in the visuals for the brand. Gillian notes, “My childhood friend is a graphic designer, and she helped me conceptualize the logo to recall the design of the 70s. Bold colors, swoopy font, just a really cool vibe.”

Gillian’s father also played a key role in helping to launch the business, assisting her with the initial equipment funds and providing key advice and guidance along the way. From here, she admits that the first year of business was both surprisingly easy and reliant, for the most part, on instinct. “I can’t say that my instincts were always right, but I have lasted almost four years, so that has to mean something!”

Uniquely sweet offerings

With this trust in her intuition, Gillian didn’t have a complete plan at the beginning, but put emphasis on carrying local, high-quality products whenever possible and focused on carrying candy that you can’t find at just any store. “I think I have been able to adapt to the needs of the town in ways that I wouldn’t necessarily have if I had a rigid plan in place.”

While her approach’s flexibility has been both helpful and challenging depending on the circumstances, Gillian appreciates that she’s stuck to her original principles over time, staying true to her own standards. She carries local ice cream and locally produced chocolate, makes all her own topping sauces and coffee syrups, and has even started crafting some of her own chocolate products!

Now offering hot chocolate in the winter, in addition to coffee, cookies, and ice cream cakes, Candy-O’s has embraced seasonality and meeting the needs of the community. “When the bakery left, I brought in cookies, so people had something to bring to parties or an afternoon snack,” Gillian shares. “I started doing espresso drinks this year to provide the after-4pm people caffeine, since that is when Irving Farm closes.”

With this capacity to change course when needed, Gillian emphasizes the significance of adaptability. This is especially important in times when plans don’t work out as expected. “Sometimes you order something thinking it will be a big hit, and it doesn’t sell at all. It’s all about understanding that if you don’t take a risk you won’t know if you get a reward or not.”

Photo by Aly Morrissey.

Managing responsibilities & spreading happiness

Gillian adds that another notable challenge has been learning through the process primarily alone. “I have had many employees that I have leaned on for support through the years, but when it comes down to it, it’s all me.”

At the end of the day, it can be overwhelming having to make all the decisions while also wearing a plethora of hats around the shop. “I play every role in the business: accountant, inventory manager, window designer, human resource manager, scheduler, ice cream scooper, chocolate maker, cashier, cleaner, handywoman,” Gillian points out. “The list doesn’t end.”

In light of this, she schedules herself in shifts as she would any employee to ensure a healthy work-life balance. “Of course, there are times when I have to fill in for someone, or work 12 days in a row, or come in on my day off to finish something that needs to be done or meet a delivery,” she acknowledges. Nevertheless, Gillian aims for at least one free day a week to prevent burnout. “No one wants a grumpy candy lady!”

Because she has so many jobs to juggle, she explains, “I wish I had taken a crash course in business to solidify the things that need to be done on the back end. But by this point I think I have it down.”

Navigating these obstacles has been worth it to Gillian because she gets to wow the people, both young and old, who walk into Candy-O’s and experience its nostalgic joy. She loves seeing customers rediscover candies they used to love. Gillian recalls, “A customer once told me that he remembered his childhood candy store and the woman who worked there. He said, ‘Hey, that’s really something. People will remember you long after you’re gone.’ That’s a really lovely thought.”

Candy-O’s is located at 28 Main Street in Millerton, NY. You can also get in contact via email at info@candy-os.com or phone at (518) 592-1600. Support them on Instagram at @candyos_sweetshop! Photos below by Aly Morrissey.