The basic timeline of Tom Caruso’s journey — from helping his grandfather make wine in South Philly to learning the ropes at an urban winery in Brooklyn, New York, to making wine on the West Coast before pulling up stakes and returning “home” — can be found on his winery website.

Pray Tell Wines, a project he started in 2017, returned with him, back to a tasting room at 1615 N. Hancock St., which sits on the border of the Olde Kensington and Fishtown neighborhoods in Philadelphia.

He and assistant winemaker/director of operations Sydney Adams have decided to return to the area of his childhood, back to where he helped his grandfather make wine using a hand-crank destemmer and basket press each fall. Indeed, they are located in the same building where Caruso’s mom and grandfather started their family business more than 30 years ago. 

“We’re a tiny operation — at the moment, a mighty team of two with help from family and friends to make the wheels roll forward,” he says on his winery homepage. “Since the beginning, the dream has been to bring world-class winemaking to the place I grew up and be near the people I love. To level up those early childhood days, using my whole body weight to move the hand-crank destemmer and basket press by incorporating state-of-the-art equipment and years of professional experience.

Caruso spent some time last week answering in detail a few questions from PennLive, providing plenty of depth to a full circle that covered more than 6,000 miles with a number of stops along the way.

Q, How did you come up with the winery name?

A, Being in a big Italian family means that there’s never a shortage of free opinions! When I told everyone that I was going to start my own winery project, they immediately jumped into action with suggestions like “Tommy’s Wines” for the label. At one point, I looked at someone in the room and jokingly asked, “And what do you think, pray tell?” Before I could let them finish, I stopped in my tracks and thought, “That’s it!” I love that it is an expression of earnest curiosity, but also a bit tongue-in-cheek. A daily reminder to continue to make our wines with serious ambition and focus, but never take ourselves too seriously! I design all of the label artwork myself as a paper collage. Mostly inspired by the later Henri Matisse period, where he stopped painting and started cutting things out. I love the idea that something beautiful can be made from something so simple. Feels like a beautiful synergy to winemaking.

Q, Fill in the timeline in terms of where you worked in Brooklyn, how long you were there, and what got you to Oregon.

A, Growing up, I would make wine on the sidewalk of my grandfather’s house in South Philadelphia. While my exposure to global wines was somewhat limited, as we only drank our family’s wine, my understanding of the basic mechanics of winemaking was instilled in me at a young age. It was once I moved to NYC after college that my curiosity around wine began to increase. With such a dynamic culinary scene, I began taking an interest in wines, as I loved meal pairings and this idea of tasting where the wines were from. I lived in Brooklyn near a winery, and one night I stopped by to ask if they needed any help in the cellar — bottling, volunteering, or whatever. Timing was fortuitous as it was late summer and harvest was approaching. I kept my day job as a book editor at Wiley and would work the night shift for the winery from 5:30 p.m. well into the early morning hours. For two months, we processed grapes from New York and California, which was really eye-opening to see similarities and differences in the cellar. I was so enamored with that experience and the possibility of having a proper winery in the heart of a city that an early dream came to mind of opening my own winery in Philadelphia someday.

From there, I enrolled in a sommelier program through the Court of Master Sommeliers. A six-month intensive course taught exclusively by master sommeliers, where three nights per week we would meet for four hours at a time and practice theory for two hours/blind taste 8-10 different wines for the other two hours. I passed my certification exams, yet still found myself thinking about and feeling drawn to the nuts and bolts of how wines were made. I decided to quit my day job and move to Sonoma. My first job in California was in the tasting room at [now-closed] Petroni Vineyards, an Italian-centric winery making “Brunello di Sonoma” — the only exception to the DOCG laws around naming regulations outside of Italy. Turns out the owner of the winery, being from Italy and owning a famous restaurant in North Beach, flew the entire governing board from Italy out to California and managed to convince them to allow him to use the name. Years later after his passing, I believe they’ve since revoked that naming right. In August of 2014, I began working for Bedrock Wine Company, A project started by Master of Wine Morgan Twain-Peterson. His expertise in historic vineyards across California and familiarity with everyone as the son of Ravenswood founder, Joel Peterson, was amazing to work alongside and learn from. I count myself as lucky to have been able to walk the rows of some of the most prestigious vineyards in California.

Q, From there, Oregon? How did that go and what brought you back to Philly?

Toward the end of harvest, my only developing plan was to take a road trip up to the Willamette Valley. It was always the shortest chapter in any textbook (ironic now, as I often find Pennsylvania viticulture to take that mantle), and I wanted to see firsthand what the region was all about. I went up to Oregon for a whopping 48 hours. I tasted regional icons like Beaux Freres, Penner-Ash, and Sokol Blosser. Before I left, I put my name in for an apartment in Portland. No job, no plans. Just a pure compulsion to be a part of what felt like the ground floor of something truly special — this wild west, sky’s the limit, bootstrapping region where the emphasis on “rising tides raise all ships” feeling palpable. I wanted to be a part of that community and contribute, as I absolutely loved the wines and people I had met. A week later, I moved up and began looking for work. I landed a job at Rex Hill, a winery established in the early days of the Willamette Valley’s history. With the first commercial plantings in the region going in the ground in 1965, Rex Hill was soon on board in the 1970s, working with grapes grown across the valley. I worked in the cellar and in the tasting room, which allowed me to continue learning production, but also how to talk about it to guests. I moved on to work with one of Oregon’s largest vineyard management companies. Lots of time spent walking vine rows and driving from place to place. The beauty of that was to feel the diurnal shift across the day in every corner of the region. To pick up the dirt, feel the elevation climbs [mostly in my legs], and notice so many intricacies of micro-climate/terroir shifts.

Pray Tell Wines

Tom Caruso and Sydney Adams, working out of their Philly tasting room, which is open Thursdays through Saturdays.Pray Tell Wines

One thing became abundantly clear as my knowledge of the region increased — Oregon’s targets were set on Burgundy. From single-vineyard expressions of Pinot Noir to finely focused bottlings of clonal selections, there was an abundance of metadata for a wine dork like me. But with all of that specialization of terroir focus, I found myself wondering about blending. Blending grapes from different vineyard sites or grape varieties in an effort to elevate the wine on the table. Add more colors to the proverbial palette. I was introduced to Maggie Harrison at Antica Terra, and her philosophy and approach were exactly the curious energy I was seeking. There’s a sense of soul in her wines that I’ve always admired, so working in her cellar was truly a formative experience.

It was in 2017, while working at Antica Terra that I received a phone call from a friend and fellow winemaker. I had always wanted to work with Gamay Noir as I enjoy the levity and playfulness that the variety can have. He had found a block of some Gamay at a nearby vineyard and asked if I wanted to split it — I could make my own five barrels of Gamay in his cellar. I quit my job and jumped into the deep end. Pray Tell’s journey began with just 120 cases of that very wine. As I looked around in that experience, I began to wonder how I might build out my own operation. I rented a 1000-square-foot warehouse space in McMinnville, signed a few more fruit contracts to bring in Pinot Noir, Chardonnay, and even more Gamay the following year, and began to seek out used equipment and barrels. With no funding and a whole lot of waiting time before I could start selling wine, I answered an online job ad that read somewhat like a late-night infomercial: “Are you a winemaker looking for a part-time job?” “Yes!” It was cryptic, with no employer information other than it was a wine import company selling smaller, artisanal producers direct-to-consumer. I scheduled an interview, and before I could even say my name on the call, the voice on the other line interjected, “What’s with the 610 area code?” I replied that I was from Philadelphia, and he offered me the job on the spot. Turns out the owner I was speaking with was also from Pennsylvania, and he knew we were hard workers back east.

I worked for that company for five years while I put every penny the winery made back into the project. From 120 cases in the first year, I had increased to about 2,000 cases by 2022, working with 8-10 different grape varieties and even more vineyards. I had largely operated as a one-man band during those first seven years, selling the majority of wine in distribution across the country and finding strong reception and some lovely accolades along the way. By that point, I had felt ready to make a big jump: move the winery 3,000 miles across the country back to my hometown. I missed family, friends, the city, good sandwiches, and regular viewing of Eagles games. I was also entirely curious about East Coast viticulture. I constantly kept an eye on projects popping up in PA and across the mid-Atlantic. I became friendly with a few producers out this way and felt like the culture here was poised to become a truly unique and special wine destination. I’ve loved tasting and learning more about viticulture and winemaking here, and similar to my initial feelings toward Oregon, felt entirely compelled to be a part of this wave.

Pray Tell Wines

Says Tom Caruso of the Pray Tell Wines tasting room: ‘We also host a number of private tastings/events as well as ticketed special events such as vertical tastings, hosting visiting chefs for brunch or dinner pairing events, and feature other local business collaborations and pop ups.’Pray Tell Wines

We filled five 53-foot tractor-trailers with barrels and equipment and set out for Philly. It took us about two years to build out the winery and get all of our licensing, but we opened in August 2024. We started making all of our wine right here in Philadelphia by September, and we’re gearing up to release some really special wines in the next few weeks. It feels great to be here, and we can’t wait to show everyone what we’re up to with our first fully East Coast wines!

Q, Winemakers/owners have their goals in terms of style and wines. What are you aiming for with Pray Tell?

A, I firmly believe that we can make world-class wines in Philadelphia, working with grapes grown in PA and across the mid-Atlantic. My approach is always geared toward fulfilling three values: honoring varietal typicity, showcasing the terroir — the land, the climate, and the growing season — and finally, showing our creative decision-making during the production process. We do this with both our single varietal expressions as well as through the many different blends that we make.

Q, Do you have a couple of pics of the tasting room/production area you can send me? When is it open?

A, The tasting room is currently open to the public Thursdays through Saturdays from 3 to 8 p.m. We require all guests be 21+ and offer outdoor seating in nice weather, a parking lot for our guests to use during their visit, and we even feature local beer and non-alcoholic options. We also host a number of private tastings/events as well as ticketed special events such as vertical tastings, hosting visiting chefs for brunch or dinner pairing events, and feature other local business collaborations and pop-ups. We made a collaborative cheese with our wonderfully talented neighbors at Perrystead Dairy and have a few other projects in the works. The space is open concept, so guests sit among the production equipment and are able to get a front-row seat to harvest in the fall. We love that this serves as an opportunity to demystify the winemaking process and offer educational opportunities.

Here are winery FAQs, per the website.

I didn’t quite get into Sydney’s story as I realize those weren’t included questions, but in short, she’s worked harvest in Abruzzo, Italy, and alongside me at Pray Tell since 2022. She had been an acclaimed sommelier in Los Angeles, working for the No. 1 restaurant in the city at Anajak Thai as well as running beverage programs at other restaurants across Southern California. We had met while she was selling the Pray Tell wines through a small artisanal distribution company, and I was lucky enough to have her join me on this next chapter and journey east!

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