Sip n’ Play SnapKu at Game Night!

Wednesday, October 14 • 6:30 PM - 8:30 PM

We are proud to serve as a Local SnapKu Ambassador, hosting SnapKu Game Night — a witty, interactive word game experience

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 (monthly every 2nd Wednesday) is a great way to meet new people, try something new, and enjoy handcrafted wine and food in a relaxed, welcoming space.

Live Music! Band Brulee

Friday, October 16 • 7 PM - 9 PM

A great jazz-infused, Americana-marinated, alt-pop band from Washington DC



Vino Vinyasa Wine and Yoga Class!

Saturday, October 17 • 10:30 AM - 12 PM

Get ready to unwind and find your inner zen as class instructor Catey Miller of Fuel Fitness LLC helps you tap into your sensory awareness as she guides your body to flow and move while building strength, flexibility, balance, and focus. Whether you're a beginner or experienced, this event is open to all levels.

Following the invigorating Vinyasa yoga session, treat your taste buds to a delightful wine tasting experience. Sample a variety of exquisite wines that have been carefully selected to complement your yoga experience. 

Live Music! Rock Salt and Bluegrass

Saturday, October 17 • 7 PM - 9 PM

Enjoy some great tunes over drinks and dinner as Brad & John take the stage!

Rock Salt & Grass brings folk-rock energy and bluegrass soul to every stage. Featuring Brad Pitt and John Schneider, the duo delivers tight harmonies, lively rhythms, and crowd-favorite classics that keep audiences singing along.

Sip 'n Paint Class!

Sunday, October 18 • 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.

Bring your friends, enjoy a glass of wine, and let the creativity flow!

Salsa Class!

Wednesday, October 22 • 5 PM - 6 PM

Try something different at The Urban Winery — a beginner salsa class designed for all levels. Come dance, connect, and have fun!



Get ready to move and have fun with an energetic beginner-friendly salsa class by Salsa with Silvia! No previous dance experience or partner is needed.The instructor will guide participants through the basic steps and rhythms of salsa in a welcoming and easy-to-follow way. Just bring comfortable shoes and come ready to dance!

Live Music! Czars of Leisure

Friday, October 23 • 7 PM - 9 PM

Enjoy some great tunes over drinks and dinner as Greg takes the stage!

Czars of Leisure is the recording and musical project fronted by Greg Roth, a singer/songwriter/multi-instrumentalist producing “thrift store rock”, which mixes the secondhand stylings of 70s power pop, 80s new wave, 90s college/slacker alternative, and 00s indie/garage rock



Live Music! Gilly and the Book Jazz Quintet

Saturday, October 24 • 7 PM - 9 PM

Enjoy some great tunes over drinks and dinner as Gilly and the Quintet take the stage

The Gilly and Book Quintet is a premier straight-ahead jazz quintet based in the DMV area. Comprised of dedicated local music educators and professional performers, the group features John Gillenwater (trumpet), Alex Silverbook (saxophone), Greg Casement (drums), Michael Grasso (keyboard), and Bob Dodelin (bass).

Live Music! Joe Kenney

Friday, October 30 • 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.

RSI Presents: Cellar Sessions - Halloween DJ Night!

Saturday, October 31 • 7 PM - 11 PM

Join us at The Urban Winery for an unforgettable Halloween with a variety of DJ's

Come taste the wine, food, & dance with us to selections from several DJ's. Costumes welcome!

Live Music! Julie Mack Brazilian Jazz

Thursday, November 5 • 7 PM - 9 PM

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.

With Julie’s rich, velvety voice and the band’s infectious energy and top-tier musicianship, this will be an unforgettable evening. Sip, sway, and immerse yourself in the vibrant rhythms of Brazil—right here at The Urban Winery.

Live Music! Flo Anito

Friday, November 6 • 7 PM - 9 PM

A classically trained vocalist, pianist, and cellist, Flo blends influences from jazz, folk, pop, and Americana into a sound all her own.

Flo Anito has performed at premier venues including Wolf Trap, Strathmore, Merriweather Post Pavilion, Blues Alley, The Fillmore, and The Birchmere, and recently completed her first European tour. An award-winning songwriter with multiple Wammie nominations, her powerful voice and captivating stage presence continue to wow audiences on both sides of the Atlantic.

Live Music! Mark Keenan

Saturday, November 7 • 7 PM - 9 PM

Mark Keenan is a songwriter, singer, and guitarist with a passion for writing about family, love, pain, and redemption. Mark has written dozens of songs and has completed two albums with his band Giant City—Still Makin’ It Real in 2000 and Brothers and Friends in 2013. Influenced by the likes of Bob Dylan, Tom Petty, and Warren Zevon, Mark has been writing and performing for over 30 years, from Los Angeles to Washington. A Chicago native, Mark lives in Silver Spring, Maryland with his wife and three children.

Learn the art of making fresh classic homemade pasta!

Tuesday, November 10 • 6:30 PM - 8:30 PM

Join us for a hands-on culinary experience as we learn the art of making fresh, classic homemade pasta from scratch. Guided by pasta artisan Joseph Romo Baldini, you'll discover traditional techniques used to create authentic Italian pasta.

In this intimate class, you'll learn how to prepare, knead, roll, and shape fresh pasta while gaining tips and techniques you can recreate at home. Whether you're a beginner or a passionate home cook, this class offers a fun and delicious way to expand your culinary skills.

Sip n’ Play SnapKu at Game Night!

Wednesday, November 11 • 6:30 PM - 8:30 PM

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 (monthly every 2nd Wednesday) is a great way to meet new people, try something new, and enjoy handcrafted wine and food in a relaxed, welcoming space.

Live Music! Cuppa T Jones

Friday, November 13 • 7 PM - 9 PM

Cuppa T. Jones is a Maryland based guitarist and songwriter blending roots, Hill Country, and Delta blues with West African rhythms and soulful punch. Powered by slide guitar and hypnotic grooves, his live performances are raw, intimate, and deeply connected to the spiritual energy at the heart of the music.



A Winemaking Experience - featuring Pinot Gris

Saturday, November 14 • 4 PM - 6 PM

Making your own wine is an unforgettable journey. At The Urban Winery, we offer a hands-on winemaking experience in a welcoming downtown setting. Learn from experts, make key decisions about your wine, and leave with a product you’ll be proud to share. Just in time for Thanksgiving!

Live Music! Ray Castro

Saturday, November 14 • 7 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!

Live Music! Jeff Weintraub

Thursday, November 19 • 7 PM - 9 PM

Join us to hear local musician Jeff Weintraub as he performs his unique interpretations across a diverse range of musical genres.

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! Seth Witcher

Friday, November 20 • 7 PM - 9 PM

Hailing from Allentown, Pennsylvania, Seth Witcher is a dynamic creative force, exuding the essence of Emo-Core in his production, performance, and visual artistry. With soul-penetrating lyrics and melodies, Seth envisions his music as a guiding light through life's shadows, weaving an eclectic tapestry across Pop, Punk, Indie, Singer-Songwriter, and RnB.

In Seth's narrative, music transcends; it heals, empowers, and celebrates vulnerability. Though independent, he won a ticket to Hollywood Week on season 24 of American Idol and has shared stages with 24kGoldn, Games We Play, Ryan Cabrera, robbietheused, Earshot, J.R. Richards, and The Orchestra (Formerly ELO Part ll).

Live Music! Ghost Rodeo

Saturday, November 21 • 7 PM - 9 PM

Gear up for some great tunes as Ghost Rodeo takes the stage.

Ghost Rodeo are versatile musicians capable of rocking out any decade or genre. From blues and funk to rock hits of the 70’s, 80’s and 90’s, along with the band grooves of the Grateful Dead. They deliver a high-energy show with plenty of crowd favorites and deep cuts.

Live Music! Rebecca Berlin

Saturday, November 28 • 7 PM - 9 PM

If Sara Bareilles collided with Joni Mitchell in a bar and had an honest conversation, it might sound like a Rebecca Berlin song. Known for being earnest, raw and pleasantly quirky, Rebecca’s style is folk, with a twist of pop, jazz and musical theater and she leaves audiences with a lasting impression. Rebecca is a winner of MASC accolades for both song (2023/2025) and video (2024) content, 2024 WAMMY nominee, Focus Music’s 2024 Rising Artist Award Recipient and Winner of the 2024 South Florida Folk and Acoustic Music Festival Songwriter. Her latest, album, "Questions and Answers", was released in May 2026, and “Live from Hungary” in August 2026.