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! 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.

Sip 'n Paint Class!

Sunday, Mar 1st , 5 PM - 8 PM

Looking for a creative way to unwind? Join us at The Urban Winery of Silver Spring for a fun and laid-back evening of painting, sipping, and socializing! Whether you're a seasoned artist or a first-timer, our Sip 'n Paint Class is the perfect way to relax, have fun, and discover your artistic flair with the guidance of our amazing instructor, Emily Gould.

✨ Your Ticket Includes: 🎨 2-3 hours of step-by-step painting instruction🖌️ All art supplies + a 16″ x 20″ canvas🍷 A glass of Urban Winery wine to sip on💲 Only $45 per person

Live Music! The Jeff Carmella Trio

Friday, Mar 6th, 7 PM - 9 PM

The Urban Winery hosts The Jeff Carmella Trio with Bam Felman on drums and Bill Enderlin on bass, playing blues, rock, and country hits!

Jeff leads the group as it delivers a delightful mix of blues, rock, and country favorites that you’re sure to recognize and enjoy.

Live Music! Rich Battaglia

Saturday, Mar 7th - 7 PM - 9 PM

Rich Diego Battaglia has been performing in the area for over 30 years. Originally from Philly, he studied classical guitar and voice at Temple University. His set list is extensive and includes a lot of John Prine, Paul Simon, Jackson Brown, Leonard Cohen, Donovan, Bob Dylan, Beatles and Rolling Stones. He will also sneak in (unannounced) some original songs, and an occasional Lute piece from the Renaissance.

Vino Vinyasa Wine and Yoga Class!

Sunday, Mar 8th, 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!

Maryland Wine Class

Sunday, Mar 8th, 5:30 PM - 8 PM

March is MD Wine Month! Join our Sommelier, Damon as we explore all that MD wine has to offer in an hour and a half class.

We will taste a variety of wines paired with small bites as we chat about the process & history of winemaking, the deductive tasting method, and answer any wine related questions you may have in our round table discussion! Taste. Learn. and Create new experiences here with us at The Urban Winery

Boards & Barrels Game Night: Sip N’ Play SnapKu

Wednesday, Mar 11, 6:30 PM - 8:30 PM

Sip N’ Play SnapKu is popping up as a featured experience during Boards & Barrels Game Night at Urban Winery — a proud SnapKu Ambassador — and you’re invited! As part of Urban Winery’s weekly Boards & Barrels Game Night, jump into SnapKu — a fast-paced, haiku-inspired word game that sparks laughter, creativity, and connection, perfectly paired with great wine and great company.

Live Music! Julie Mack Brazilian Jazz

Thursday, Mar 12 from 7 pm to 9 pm

Get ready to unwind at The Urban Winery’s Live Music Night featuring the mesmerizing vocals of Julie Mack and the dynamic Brazilian Jazz Band, Encantada! Renowned for their electrifying shows, Encantada blends Brazilian samba, bossa nova, and baião with the smooth elegance of U.S. jazz for a one-of-a-kind experience.

Sip and Shuck - Oysters and All Night Happy Hour

Friday, Mar 13th, 6 PM - 8 PM

Get ready to indulge in the perfect pairing of oysters and wine! Our favorite oyster shucker will be on hand along with all night Happy Hr.

Get ready to savor the sea at The Urban Winery from 6-8pm. Guests can indulge in oysters freshly shucked onsite (or grilled), bringing the briny magic of the coast straight to your plate. Pair each bite with our carefully curated wines for a perfect match. And of course, our full regular menu will be available. Happy Hour pricing continues into the evening until we close.

Live Music! 909

Saturday, Mar 14th, 7 PM - 9 PM

909 is Montgomery County’s premier 90s rock band - join us to hear some great tunes and enjoy great wine and food along with.

909 is Montgomery County’s premier 90s rock band. With seasoned musicians, note-perfect covers of 90s rock hits, and a high energy show, they’ve been lighting up venues across MoCo. So come out to this free show and relive your favorite hits, or discover new songs you might just love!

Live Music! Jeff Weintraub

Thursday, Mar 19 from 7 pm to 9 pm

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! Evelyn Acht

Saturday, Mar 21st from 7 pm to 9 pm

With a soulful voice and acoustic guitar, German-American musician Evelyn Acht invites listeners into her world. Inspired by 70s singer-songwriters like Joan Baez and Joni Mitchell, Evelyn blends original songs with meaningful covers, sharing stories from her life that are gentle, honest, and quietly powerful.

Live Music! Wendy and the Lost Boys

Friday, Mar 27th, 7 PM - 9 PM

Get ready to rock out with Wendy and the Lost Boys at a great live music event - it's gonna be one for the books!

Wendy and the Lost Boys get you dancing with their New Orleans-style fun and funky sound. Originals and faves from artists such as Jon Cleary, Tab Benoit, and the Meters keep things rockin, with tunes from Steely Dan, Bonnie Raitt and Freddy King rounding out the mix. With David Uffelman, vocals; Steve Wilmarth, guitar; Nick Newlin, keys; Wendy Lanxner, bass & vocals; and Carrie Slenkovich on drums.

Live Music! The Juliet Lloyd Duo

Saturday, Mar 28th, 7 PM - 9 PM

The Juliet Lloyd Duo showcases Juliet’s powerful vocals and songwriting alongside guitarist Steve Quintilian.

The Juliet Lloyd Duo delivers intimate performances that blend heartfelt originals with dynamic covers. Performing regularly across Maryland and the greater DC/VA region, the duo brings a warm, engaging energy to the winery.