The 16th Annual Highlandtown Wine Festival

Come and join us for the 16th Annual Highlandtown Wine Festival on Sunday, May 5, 2019! 

The annual street festival in southeast brings more than a thousand visitors to partake in homemade wine, eat fine Italian food, listen to live music and have fun.

Presented by the Highlandtown Community Association and DiPasquale's Italian Market, The festival takes place Sunday, May 5th, from 1 to 6 p.m. at Our Lady of Pompei Convent Garden (3600 Claremont St.)

Please see the Highlandtown Wine Festival Facebook page for updates as we get closer to the event!

Food & Wine

Admission to the festival includes five complimentary tastings of homemade wines, including vintages like the Highlandtown Red and Bel Air Zin. In addition to the complimentary antipasti, DiPasquale's will have meatball subs, sausage and peppers, pasta, cannolis and their specialty arancine -- as seen on Food Network– available for sale.

The festival features a competition for amateur winemakers judged by Baltimore’s finest celebrities and connoisseurs.  Bronze, silver and gold ribbons will be awarded to the best red and white wines based on appearance, smell, taste and overall quality. Contestants also compete for the best bottle design.

Wine competition entry forms are available online at, as well as at

DiPasquale's (3700 Gough St.) and Mastellone Deli & Wine (7212 Harford Rd.).


Tickets for people 21 and over are $25 ($20 in advance), and include a souvenir wine glass and a selection of antipasti from DiPasquale’s. Children and teens can enter free with an adult, but sorry, no wine.

For tickets in person, visit DiPasquale’s, The Laughing Pint, Mastellone Deli & Wine, or Rust-N-Shine.


 Over the past twelve years, the festival has raised over $40,000 to support Highlandtown

Community Association initiatives including street improvements, grants for sculptures in

Patterson Park through the South East Community Development Corporation, the Movies in

the Park series at Patterson Park, Highlandtown Arts District activities, neighborhood greening

projects, and repair and cleaning projects at Our Lady of Pompei church.