Alexandra Occhicone and Arianna Milanese always talked about opening a restaurant together, but neither of them thought they’d actually go through with it.

Until they did.

“I saw this place was for rent and I sent the video to Alex as a joke,” Ari says. “But then my fiancé pushed us to do it, so we met with the landlord.”

What was once a dream very quickly turned into reality, and in just eleven short months, The Bar on West & Main opened its doors to the Pleasant Valley, NY community.

“We were so nervous because we didn’t know how the town would respond to our opening and how much support we would get, but our customers really showed up for us,” says Ari.

Owners Alex Occhicone and Ari Milanese

Both have strong ties to the Pleasant Valley area, so when they saw that the building was for rent on West Road, they jumped at the chance.

“We built such strong relationships with the people here that it just feels like home,” says Alex.

Alex and Ari say that they have customers coming from all over, including Millbrook, Rhinebeck, and Newburgh. Additionally, a few videos on their Tiktok account have gone viral, resulting in customers coming from even further away.

“This one couple came from Connecticut one Sunday and said that they came across our Tiktok and wanted to check us out,” Ari says. “It’s pretty cool to see people come from all over.”

The inspiration to open West & Main came from Alex and Ari’s vast experience in restaurant hospitality. Both have spent their careers working in restaurants in varying capacities.

“I have always had a love for the industry,” says Alex. “I love catering to people. I love seeing people happy, and doing something that brings people together has always been a true passion of mine. Ari shares a very similar passion to mine, so we just took a chance.”

Ari grew up working in her grandparents’ restaurant, Milanese, in Poughkeepsie. There, she says she learned her hospitality skills from her grandfather.

“I was raised in the atmosphere of building personal relationships in the restaurant business. My grandfather would walk around and do magic tricks and make people laugh. I think because of that I just love talking to people, I love meeting new people and making them feel comfortable,” she says.

Ari and Alex say that the biggest challenge of opening was getting everything to come together at once in time for the opening.

“We thought we were ready, and then we realized that we forgot to buy a phone!” Ari laughs.

“We found one on Facebook marketplace and then it didn’t even work!” Alex adds.

Ari says that Jay from Jason Patrick’s on Route 44 ended up giving West & Main a phone hours before they opened their doors.

Another one of the challenges that Alex mentions is the difficulty of balancing work with their lives as full-time moms. Ari and her partner, Paris, have three kids that she homeschools, while Alex and her partner Nick have four kids combined.

“We’re trying to balance our lives as moms at home, as well as work and meetings and everything you need to do in order to run a business. It’s always trying to balance it correctly and it’s really hard sometimes, but we always do it,” she says.

Alex and Ari are also quick to mention the vital role that their significant others played in opening the restaurant. Paris and Nick serve as the primary builders and fix-it-all guys, and during the build, they spent every night at the restaurant making Alex and Ari’s vision come alive.

Alex and Ari also say that one of their biggest personal challenges was transitioning from an employee position to now being the owners and being the ones who are in charge.

“I think it’s hard for me, because I don’t like being in authority. I always make Alex do everything with that,” Ari laughs.

One of the most important things to them as owners is maintaining good management. They share that because they very recently made the transition from working for somebody else to now being in charge, the dynamic of being an employee is still very fresh in their minds.  As such, they try to ensure that their management is as organized and kind as possible so their employees never feel overwhelmed or stressed out.

“A lot of customers say that to me, too,” Ari says. “I had a customer say, ‘You can tell that you guys are such good bosses, because it’s a trickle down effect and I can see it through your employees.’ That was a really nice compliment to get.”

Another element that is important for Alex and Ari is changing their menu regularly. West & Main changes their cocktail and food menus seasonally in order to stay as fresh and different as possible, and they’re currently on their second menu since opening in January.

The “West & Main Crostini”

“We like to keep it fresh and interesting with new ideas,” Alex says.

Additionally, they shared that they have a new chef starting at West & Main and they plan on altering the menu slightly to add more “cool and different” small plate offerings and appetizers.

“The chef that we have coming in has a really good following and a lot of experience, so I think that in the upcoming months, our menu is going to take a turn and we’re going to have a lot of fun new dishes,” says Ari.

Some of the current cocktails on the menu include “Let’s Get Fizzzzzical,” made with tequila, watermelon puree, lemon juice, prosecco, and club soda, “Beach, Please!” made with Malibu rum, pineapple juice, cranberry juice, peach schnapps, and creamer, and “The Best Figgin’ Mule,” a take on the classic mule, but made with fig vodka instead.

“We wanted the names of our cocktails to be quirky and fun, and we also wanted to match our cocktails to what this place is,” Alex says. “You can come in and get your rum and coke, but you can also get a really nice, fun cocktail, too.”

Some of the small plates offerings currently include, “Frickles,” or fried pickles, served with a tomato smoke bacon spread, the “West & Main Crostini,” served with whipped ricotta and a grilled peach crostini with honey drizzle and pistachios, and the stand-out, “General Tso’s Crispy Cauliflower,” which is made up of crispy beer battered florets, sesame seeds, cherry peppers, and general tso’s sauce.

“We change things seasonally, and it’s hard because some people are always like, ‘oh, why did you take this off the menu? It was so good!’ but then you get the opportunity to open your palate to something new,” says Alex.

West & Main also carries a variety of local beers on draft including Millhouse, based out of Fishkill, Sloop, based out of Poughkeepsie, Newburgh Brown Ale, based out of Newburgh, and Industrial Arts out of Beacon. Ari notes that they only do quarter kegs in an attempt to keep everything as fresh as possible, so they are constantly switching out beers.

Perhaps one of the things that West & Main is best known for is their monthly themed events.

On the first Sunday of every month, they host the “Night in the Day DJ” from 1-5pm. It’s a perfect event for those who like to be tucked in bed by 10 pm sharp and those who have young children and therefore have difficulty going to events at night.

Another popular event is Ladies Night, which takes place on the last Friday of every month and coincides with live acoustic music. The event goes from 7:30 to midnight, during which ladies specialty cocktails are available for $5.

The most popular and meaningful event by far, however, is their karaoke campaigns, which take place on the second Thursday of every month from 8-11pm. The campaigns are hosted in honor of a different local family in need every month, with 10% of all of the night’s proceeds going to that family, as well as the money from a 50/50 raffle.

“I really truly do love to give back and help people whether it’s emotionally, financially, like if I can do anything, I will,” says Ari. “I’ve done fundraisers before and when I found out we were going to be business owners and have our own space, it was like why not? There’s no reason not to.”

Ari and Alex say that giving back is one of West & Main’s core values.

Paris and Nick

“This is our town, and some of the people in our town are living absolute nightmares. It’s so important for us to give back and do that for others. That’s one event that I would never want to ever give up.”

Looking forward, Alex and Ari have their sights set on opening up an event space or wedding venue.

“That’s our dream!” Ari says. “Well, this was our dream and we made it happen [laughs], so that’s our next dream!”

The Bar on West & Main
18 West Rd. Pleasant Valley, NY 12569
(845) 723-4117