Yappy Hour - Hello canines!

Starting Tuesday, April 7th - 5 PM - 8 PM

Join us every Tuesday on our outdoor patio (plenty of umbrellas for shade) with your best friend to enjoy extended Yappy (aka Happy) Hour.

Bring your dog and enjoy all night happy hour. Water and treats provided for our special guests!

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.

Boards & Barrels Game Night: Sip N’ Play SnapKu

Every SECOND Wednesday of each calendar month. Next one on 4-8 from 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! Joe Kenney

Saturday, April 4th - 7 PM - 9 PM

The Urban Winery hosts Joe Kenney, a Philadelphia-based award-winning multi-genre pianist, composer, and recording artist.

Joe blends a cool jazz fusion vibe with jam-band influences, to create a distinctive and dynamic energy that comes to life in captivating originals and distinctive arrangements of contemporary tunes from varying genres/origins.

Live Music! Cameron Markott

Friday, Apr 10th, 7 PM - 9 PM

With boots on a path of her own making, wandering like a modern-day gypsy, Cameron turns life’s struggles into songs of heartfelt reflection. A Berklee College of Music graduate, she has earned recognition, including the 2023 Best International Song award from the Wild Filmmakers Festival and is set to bring her first tour to ten states this season. She features an eclectic mix of music, ranging several decades of songs, in the country and classic rock genre, as well as her own music in her performances and is so excited to bring her songs to the winery.

Live Music! Rock Creek Revival Bluegrass

Saturday, April 11th, 7 PM - 9 PM

Spend a spring evening enjoying great wine, great food and great music, featuring Rock Creek Revival Bluegrass.

Rock Creek Revival is a Maryland-based band that draws inspiration from the broad history of bluegrass, from first generation pioneers like Bill Monroe and Jimmy Martin to more contemporary acts such as Hot Rize and Yonder Mountain String Band.

April Sip 'n Paint Class!

Sunday, Apr 12th - 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.

Live Music! Verona's Court

Friday, Apr 17th - 7 PM - 9 PM

Verona’s Court is a five-piece band from the DMV blending soulful vocals, pop-rock energy, and a touch of R&B. Their feel-good mix of fan-favorite covers and originals keeps crowds singing and dancing all night long.

Live Music! JJ Warren Band

Saturday, Apr 18th - 7 PM - 9 PM

Formed in July 2025, the JJ Warren Band is the newest country band breaking onto the scene.

Fronted by JJ Warren and Elle, this group brings a dynamic and high-energy approach to their music that is immediately infectious, blending classic country roots with a sharp, contemporary groove.

Corks and Cars Show with live music

Wednesday, Apr 22, 5 PM to 9 PM

Spend your evening at The Urban Winery where classic car lovers can revel in vintage vehicles while sipping wine and enjoying great food.

Corks and Cars Show. Spend an evening at The Urban Winery of Silver Spring, where classic car aficionados and all guests can revel in vintage vehicles while sipping on fine wines and enjoying great food. Live music featuring Philip LoPiccolo from 6-8pm

RSVP OPTIONAL - ALL ARE WELCOME REGARDLESS OF RSVP STATUS

Whether you're a car enthusiast or just looking for a fun evening out, this event is perfect for everyone. Don't miss out on this unique blend of wine, music, and wheels! 🛞 🍷

Live Music! Tom Rohde

Friday, Apr 24th - 7 PM - 9 PM

The Urban Winery hosts Tom Rohde, a versatile classical guitarist who performs across a wide range of settings and styles.

His repertoire highlights pieces from the classical guitar tradition—including Spanish and Latin American works and Baroque and Classical-era music—alongside arrangements of bossa nova and samba classics.

Live Music! Big Howdy

Saturday, Apr 25th - 7 PM - 9 PM

Big Howdy is an award-winning progressive bluegrass band known for its powerful lead singing, rich vocal harmonies, and instrumental chops.

With a repertoire that mixes bluegrass classics with emotionally compelling original songs, intriguingly novel instrumentals, and well-chosen contemporary material, Big Howdy presents bluegrass with modern polish while honoring the drive that lies at the heart of the music.

Vino Vinyasa Wine and Yoga Class!

Sunday, Apr 26th - 10:30 AM - 12 PM

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!