In 2003, James Smallwood stepped into 33 Wine Shop & Bar at 1913 Park Ave. as a corporate cost analyst with curiosity to spare but little experience navigating a wine list. But as years of business dinners grew into dedicated self-study and moonlighting at restaurants, Smallwood’s early curiosity grew into a devotion to wine that would eventually reshape his life. Smallwood traded his corporate role at AT&T and dove fully into the world of wine, completing formal classes, earning sommelier credentials and eventually guiding a friend’s restaurant as wine director and general manager.
By 2013, Smallwood had acquired 33 Wine Shop, originally started by Jake Hafner of Civil Life Brewing Co. For Smallwood, the business was more than a bar, it was a place that modeled the kind of hospitality, education and community he wanted to cultivate.
Jessica Spitzer’s path to 33 Wine Shop was just as unconventional. With a background in nonprofit work and reentry programs, she never envisioned herself running a wine bar. That changed in 2019 when she met Smallwood at the bar. Their relationship grew quickly, and by early 2020, Spitzer began helping with the administrative side of the business. Then the pandemic hit. What began as administrative support blossomed into a full-fledged wine education. With Smallwood’s mentorship, Spitzer honed her palate, earned her introductory sommelier credentials and now shapes both the operational and tasting experience at the bar.
Together, Smallwood and Spitzer have upheld 33 Wine Shop’s tradition: a local bar where exceptional wine meets warm, welcoming service. The pair prioritizes approachable wine education, guiding guests through tastings, classes or personal introductions to unexpected bottles. Their popular wine club reflects that philosophy. With three tiers and a monthly red and white selection handpicked by the owners, the club encourages exploration over customization. “We want our guests to discover wines they may never have tried otherwise,” Spitzer explained.
Smallwood believes 33 thrives where restraint meets quality: Old World wines kept in ideal conditions, with a tightly curated, effortlessly classic cocktail selection. At 33, every bottle rests in a carefully maintained, temperature-controlled cellar – a rarity that Smallwood insists is non-negotiable. “It’s uncommon to find a space like this,” Smallwood said of the cellar, “but keeping it temperature-controlled is absolutely essential.” But beyond the cellar, the bar’s charm lies in its human moments: the door’s creak that signals a greeting, a detail Smallwood refuses to alter, and favorite wines are remembered. Over the years, countless friendships and even marriages – Smallwood and Spitzer’s included – have begun within the bar’s walls.
Approaching its 25th anniversary, 33 Wine Shop & Bar continues to prosper under the care of its husband-and-wife duo. For Smallwood and Spitzer, it’s more than a business. It’s a community gathering place, a classroom and a love story – both with wine, and with each other.
This article appears in October 2025.