Live Music & Dining in The Haymarket Lounge
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Escape to Urban Wine Country where concerts, comedy, wine, and food come together.
What's Happening at City Winery
Live Music & Comedy
Experience live music, concerts, and stand-up comedy at City Winery Boston, featuring touring artists, established favorites, rising talent, and top comedians throughout the year. From rock concerts and live R&B to jazz, soul, folk, comedy shows, and more, our stages offer something for every audience. Settle in with dinner and award-winning wines while enjoying your performance from a seat with great sight lines.
Restaurant Specials
Brunch
10am - 3pm Saturdays & Sundays
Make City Winery your weekend brunch spot. Every Saturday and Sunday from 10 AM–3 PM, enjoy brunch classics and a DIY mimosa bar.
Burgers & Barrels
Sunday through Thursday
Join us and enjoy our Burger & Barrel special for $25. Choose from the CW Burger, Classic Smash, or Truffle Burger, perfectly paired with a tap wine of your choice.
Looking for more pairing inspiration? Read The Case for Your Summer BBQ to discover our favorite wines for burgers, barbecue, and all your summer grilling favorites.
Gameday Specials
Looking for the best place to grab food and drinks before a TD Garden event? City Winery Boston offers Pregame Specials on all Celtics, Bruins, and event nights at the Garden. Enjoy $1 oysters, clams, and shrimp from our raw bar and $8 wings, paired with award-winning wines and craft cocktails.
$20 Wine Flights
For just $20, experience a variety of wines with our thoughtfully curated flights of reds and whites
Wine and Food Events
Discover unforgettable moments with our immersive wine experiences, lively brunches, themed dinners, and expertly curated pairing events.
On Tap: Musings on Everything City Winery
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Dinner Party Trio: A Harvest Dinner in Three Pours
Dinner Party Trio is our new series: three City Winery wines chosen to follow one another through a single evening, each paired with recipes, so you have everything you need...
Dinner Party Trio: A Harvest Dinner in Three Pours
Dinner Party Trio is our new series: three City Winery wines chosen to follow one another through a single evening, each paired with recipes, so you have everything you need...
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Chicago Deep Cuts Fall 2026
Fall in Chicago has a way of turning the calendar into an argument for staying in the city instead of leaving it, and this stretch of the City Winery lineup...
Chicago Deep Cuts Fall 2026
Fall in Chicago has a way of turning the calendar into an argument for staying in the city instead of leaving it, and this stretch of the City Winery lineup...
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September Specials and How to Pair Them
This month's specials are on the board at every City Winery location, and there's a pour, or a few, in each market's wine program built to sit right alongside them.
September Specials and How to Pair Them
This month's specials are on the board at every City Winery location, and there's a pour, or a few, in each market's wine program built to sit right alongside them.
Wine & Collectibles
Harvest Season Exclusive
Receive an invite to our exclusive Thanksgiving Wine Tasting in early November when you purchase our Harvest Case or Half Case.
Merch Shop
Get cozy with a unique, one-of-a-kind City Winery hoodie or T shirt. No two are alike.
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Read MoreApril 20, 2026
"City Winery founder Michael Dorf talks about building two iconic music businesses from nothing and why sleeping under your desk is sometimes the right move."
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Read MoreJanuary 5, 2026
“Michael Dorf reflects on the evolution of City Winery, the rise of comedy programming, new restaurant concepts including El Bar, and the future of live music.”
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Read MoreApril 10, 2023
"City Winery is on track to become the most environmentally efficient direct-to-consumer winery."
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Read MoreFebruary 2, 2023
“City Winery to host fundraiser & performances in honor of Black History Month & Women's History Month”
