30-year-old Alexandra Occhicone and 31-year-old Arianna Milanese always wanted to open their own restaurant and bar, but the opportunity didn’t arise until the middle of 2022 when they found the perfect location for rent off of West Road in Pleasant Valley, NY. What followed was a seven-month process that included renovating and custom building the space, obtaining an LLC, and completing the oodles of paperwork that come along with starting a business, and on January 8, 2023, The Bar on West & Main officially opened its doors.
Building a brand from scratch
Coming up with the name was pretty easy. Alex and Ari wanted something that sounded nostalgic yet trendy, and because many locals in Pleasant Valley refer to Route 44 as “Main Street,” they decided that The Bar on West & Main had a nice ring to it.
The inspiration to open West & Main came from Alex and Ari’s lengthy experience in restaurant hospitality. They’ve spent their careers working in restaurants in varying capacities. After working together for many years, Alex and Ari began dreaming of what it would be like to own their own restaurant. With the help of Alex’s husband, Nick, and Ari’s husband, Paris, that dream very quickly came to fruition.

Photography by Julie Benedetto
“Our husbands both knew a lot about building, so we introduced them to one another and they immediately became friends and got to work to make West & Main come to life,” Ari explained. “Anything they didn’t know how to do, they learned how to do.”
It wasn’t an easy feat. When they first rented the space, it was merely four walls with a concrete floor and plumbing to one bathroom. Paris and Nick completely renovated the space – including completing the plumbing to additional bathrooms, the bar, and the kitchen; doing the wiring for the electric; and building the bar, tables, and industrial wooden shelves.
“They built everything essentially from scratch for us. It’s all custom-made,” Alex said.
The first year in business
Once opening, they hit the ground running. Within their first year, West & Main won Best of the Hudson Valley for the category of Best Bar Food, presented by Hudson Valley Magazine, and also won best appetizer at The Great Hudson Valley Cook Off.
They host themed nights throughout the month at the bar, including karaoke campaigns, which take place on the second Thursday of every month and are hosted in honor of a different local family in need each month. 10% of the night’s proceeds go to that family, as well as the money from a 50/50 raffle. Because West & Main was so successful within the first few months of being open, Alex and Ari were able to start these campaigns early on. “With the support of the community, we were and are still able to give back to the community that we love so much,” Ari said.
West & Main also hosts other themed nights, including taco Tuesdays with five-dollar margaritas, live music on Wednesdays and Fridays, and holiday themed nights and other events, including a Halloween costume-only party, black-tie New Year’s Eve party, bike nights, and late-night DJ sets.
“You have to take into account the environment that you’re in and appeal to the customers first and foremost. In the beginning, we didn’t think as much about that. We had a vision for ourselves and what we wanted, but it took a full year to figure out what works for everybody,” Alex explained.
They’re also constantly thinking about what they want to do in the future. “If we were successful, we were thinking about how to use this business to expand, but now we’re just so busy. A lot goes into this business that we didn’t anticipate,” Ari shared.
Give and take
Additionally, Alex and Ari both have small children, so learning to make sacrifices was one of the biggest lessons they had to learn. Paris and Nick built West & Main in just seven months, and for many of those days they would work their full-time jobs during the day and then go straight to the restaurant to work into the night. Likewise, it wasn’t easy on Alex and Ari either; it was both a financial strain and an emotional strain.

Photography by Julie Benedetto
“If you work hard and you’re passionate about what you do, I don’t think that there’s any way that you can fail,” Ari said. “There were times where it was tough and it still can be tough, but Alex and I respect each other as business partners and as friends. We recognize that we’re putting the same effort into this business, and we learned to make decisions together and make sacrifices for one another, too.”
Managing a work-life balance is difficult, too. Alex and Ari alternate weekends and work different days during the week so that they’re able to have time for their families and to get other everyday tasks done, but they’re never really off the clock. “We kind of divide up our jobs as far as the bar goes and we have set schedules in our personal lives, but there are times when one of us is stressed out beyond belief and has to take a step back. It’s really nice to have each other to lean on and be able to pass things off for a day or two when necessary,” Ari said.
Of course hindsight is 20/20, and for business owners, there is almost always at least one thing that they wish they knew prior to starting their business. “I wish I knew that I wouldn’t be able to go to sleep without thinking about the bar,” Ari laughed. She noted that they learned a lot during their first year, particularly about the financial side of running a business.
“I wish I would’ve realized that you have so many different people that you’re managing. They have different personalities and ways of working, and it can be hard to balance how to be a proper boss to everybody and run a business smoothly while also being empathetic and flexible,” Alex said.
On the flip side, the most rewarding part about starting the business for Alex was seeing all of their hard work and effort finally come together. “Seeing all of our work starting to take shape little by little and seeing it finally pay off, that was one of the best parts,” she said.
For Ari, one of the most rewarding parts was seeing the enthusiastic support from the community. “Seeing how many people who were watching us from behind the scenes and supporting us was surreal. It’s so cool to look around and see how many people come in to support us. People will come from all over – from New Jersey, Manhattan, Connecticut, and beyond – because they discovered us on social media. That’s really cool.” •
The Bar on West & Main is located at 18 West Road, Pleasant Valley, NY. Visit their website thebaronwestandmain.com, their Instagram @thebar.on.wm, or their Tiktok @2girls_and_abar for more information.