Boards and Barrels Game Night: Every Wednesday!

Every Wednesday, 6 PM - 9 PM

Join our Boards & Barrels game night! Enjoy top wines paired with new and classic games for an evening of fun and community. Pick from our game library or bring your favorite. Unplug. Uncork. Unbox.

Live Music! Jeff Weintraub

Thursday, Jan 15 from 7pm to 9pm

Jeff Weintraub, a talented vocalist and guitarist from the Washington area, delivers a dynamic mix of jazz, folk, country, bluegrass, blues, and timeless American Songbook classics. In this solo performance, he will showcase his unique interpretations of songs by artists such as Bob Dylan, Tom Waits, Richard Thompson, Paul Simon, Elvis Costello, and Randy Newman.

Live Music! Beyhan

Friday, Jan 16 from 7pm to 9pm

They play your favorite hits; songs you forgot how much you loved — including classics by the Police, Sade, the Righteous Brothers, The Meters, Ronstadt, Marley, Aretha, and Martha and the Vandellas.

So sit back and enjoy — or get up and dance — to tunes that will tug at your heart strings.

Live Music! Shorty Slim

Saturday, Jan 17 from 7pm to 9pm

From Washington, D.C., comes the smooth, soulful sound of Shorty Slim — a jazz-forward ensemble blending classic cool with just the right touch of funk and blues. With a setlist that flows effortlessly from Herbie Hancock to Miles Davis to John Coltrane, the group brings rich textures, tasteful grooves, and timeless melodies to every performance.

Vino Vinyasa Wine and Yoga Class!

Sunday, Jan 18 from 10:30am to 12pm

Enjoy the perfect blend of relaxation and fun with Vino Vinyasa. A class that combines yoga, wine tasting and a food board!

Live Music! Snakehead Run

Thursday, Jan 22 from 7pm to 9pm

Specializing in authentic blues jug and string band music that you might have heard on a street corner or juke joint in New Orleans, Memphis, or Louisville early in the last century we try to introduce listeners to where some of today’s music comes from, blending both the old and the new.

Sip n’ Play SnapKu at our SnapKu Game Night!

Wednesday, Jan 28 from 6:30pm to 8pm

SnapKu is a fast-paced, high-energy word game that puts a modern spin on the classic art of haiku. With multiple ways to play and win, it's a race against the clock to show off your creativity, wordplay, and quick-thinking brilliance! This free event is a great way to meet new people, try something new, and enjoy handcrafted wine and food in a relaxed, welcoming space.

Live Music! Julie Mack Brazilian Jazz

Thursday, Jan 29 from 7pm to 9pm

Join us at The Urban Winery for an unforgettable night of Brazilian jazz with Julie Mack & Encantada—great wine, music, and energy!

Sip 'n Paint Class!

Sun, Feb 1, 2026 5 PM - 8 PM

Unwind at The Urban Winery! Join our Sip 'n No experience needed—our instructor Emily Gould will guide you step by step.

Your Ticket Includes:

🎨 2–3 hours of instruction

🖌️ All supplies + 16″ x 20″ canvas

🍷 A glass of Urban Winery wine

💲 Only $45

Bring friends, sip wine, and create something beautiful!

Learn the marvelous game of Mahjong!

Tuesday, Feb 3, 2026 5:30 PM

Did you know Mahjong has been proven to strengthen cognitive function, including focus & memory, decision-making skills & logical thinking? On top of being a great way to spend time with friends & make new connections. Give it a try and join the exciting movement that is building communities of players!

Live Music! Joe Heilman

Thursday, Feb 5, 2026 7:00 PM - 9 PM

ONE VOICE. ONE GUITAR. ONE SOULFUL FORCE.

Joe Heilman grew up listening to his mother’s soul music & stealing his father’s Beatles and country records. So when he picked up an acoustic guitar what came out was a little bit of everything…and it still does!

The Urban Bloom Experience - A floral arranging workshop

Saturday, Feb 7, 2026 3:00 PM

Join us at the Winery for a floral design workshop with Beth Dincin Floral Design. Together you’ll explore how flowers can set a mood, express emotion, and spread joy. You’ll learn techniques to extend vase life, explore sustainable mechanics, and design a bouquet inspired by color, texture, and movement. And of course, enjoy some wine while you create!

Live Hungarian Music! Magnolia Zenekar & Szikra Banda

Saturday, Feb 7, 2026 7:00 PM - 9 PM

Come out and dance, or just tap your toes, to the irresistible music of the Hungarian folk tradition! Magnólia Zenekar plays authentic string band music from Hungary and Transylvania. Also appearing will be Szikra Banda, playing dance music of the Csángó Hungarian people with its energetic, ancient pulse. Both bands are DC-based and perform regularly at cultural events and dance parties throughout the Northeast.

Whiskers & Wine - A Valentine's Event

Thursday, Feb 12th, 5 PM - 8 PM

A Valentine's event to help pets in need. Join us for wine tastings, live music, prize drawings and more, all to benefit the work of the Montgomery County Humane Society!

Live Music! Ray Castro

Friday, Feb 13, 2026 7:00 PM - 9 PM

Ray “Mr. Swiftie” Castro is making his debut at The Urban Winery! He’ll be playing a full night fun acoustic covers of all of your favorite hits from the 90s and 2000s, as well as a some Taylor Swift covers mixed in for the Swifties in the crowd!Expect to hear some Green Day, Matchbox 20, Gin Blossoms, Counting Crows, Goo Goo Dolls, U2, Sublime, Hootie & the Blowfish and many more of your favorites from 90s & 2000s rock/alternative radio to bring you back to those times. Ray plays a fun and upbeat show, so it’ll definitely be a good time!

Vino Vinyasa Wine and Yoga Class!

Sunday, Feb 15, 2026 10:30 AM - Noon

Join us for an unforgettable morning of relaxation with Vino Vinyasa, a flow-based Yoga class that connects breath awareness with Yoga postures -- all while weaving in fun wine facts and history. Immerse yourself in the perfect blend of rejuvenating yoga practice and delightful wine tasting. We hope to see you there!

Craft Your Own Illuminated Decoupage Wine Bottle Art

Sunday, Feb 15, 2026 3 PM - 5 PM

Transform an ordinary wine bottle into a stunning piece of illuminated art!

Live Music! Black Shag Sherpas

Saturday, Feb 21, 2026 7 PM - 9 PM

Join us for an evening with Black Shag Sherpas, featuring a great acoustic performance. Enjoy wine and great music! Black Shag Sherpas is versatile, rhythmic, melodic, funky and pushy at the same time, with the male-female vocal mix.

Live Music! Cariel Coates

Saturday, Feb 28, 2026 7 PM - 9 PM

Cariel fuses jazz, R&B, soul, reggae, and bossa nova into a sound rooted in her Caribbean heritage. Her music radiates warmth and authenticity, blending original songs with creative takes on classics. Since moving to D.C. in 2016, she’s captivated audiences with her dynamic range and stage presence, earning features on ABC7, FOX News, and more for her dedication to inspiring others through music.