Live Music! James Margolis

Saturday, August 29 • 7 PM - 9 PM

Drawing inspiration from bluesmen like Skip James, Mississippi John Hurt, and Magic Sam. James also draws inspiration from jazz, folk, outlaw country, and soul music. With a voice that has been compared to Frank Sinatra, he is known to soulfully belt while finger-picking like Doc Watson. James has been touring regionally, up and down the East Coast and beyond, performing original songs and choice covers from the blues, folk, and soul catalogs.

Live Music! Evan Crowell

Saturday, September 5 • 7 PM - 9 PM

Chill out with some great tunes as Evan Crowell takes the stage for the unofficial end of summer weekend.

Evan brings Texas-rooted folk rock to life through solo acoustic guitar and vocals. Drawing inspiration from James Taylor to Radiohead, he blends heartfelt originals with distinctive covers.



Live Music! Bless the Ashleigh

Friday, September 11 • 7 PM - 9 PM

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

Imagine Jack Johnson's sun-bleached warmth colliding with the raw emotional gut-punch of the Avett Brothers, then drifting into unexpected ambient electric territory that nods to Buckethead's textural explorations and Hendrix's tonal spirituality.

Live Music! 909

Saturday, September 12 • 7 PM - 9 PM

Join us to hear some great tunes from this great 90's band 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!

Vino Vinyasa Wine and Yoga Class!

Sunday, September 13 • 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!

Live Music! Jeff Weintraub

Thursday, September 17 • 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! Karen Collins and the Backroads Band

Friday, September 18 • 7 PM - 9 PM

Their original songs (shuffles, two-steps, and buckle-polishing slow tunes) project an authentic vintage sound. The twang continues with a list of covers that range from Hank Williams and Ernest Tubb to Patsy Cline and Loretta Lynn with a dash of Rockabilly thrown in.

The band is lead by Karen Collins, a coal miner’s daughter from Southwest VA (vocals, rhythm guitar) and features Ira Gitlin (lead guitar, vocals), James Key (bass) and Pat Puglisi (drums, vocals).

Dogs and Wine Gathering - Toby's Rescue

Saturday, September 19 • 3 PM - 6 PM

Toby's Rescue alumni are gathering for a fun in-person meet-up. This event, while focused on families who have worked with Toby's is open to all dog lovers where you can relax and enjoy some delicious wine with your canines.



Live Music! The Jeff Carmella Trio

Saturday, September 19 • 7 PM - 9 PM

Jeff Carmella blends roots rock, surf, rockabilly, jazz, blues & more, crafting a unique sound that fans love to hear.

Join us for an unforgettable evening at The Urban Winery featuring the incredible Jeff Carmella Trio. Experience live music that will captivate and energize you! And of course great wine etc...

Sip 'n Paint Class!

Sunday, September 20 • 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!

Cars and Corks Show with live music

Wednesday, September 23 • 5 PM - 9 PM

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, (beers and spirits along with mocktails too) and enjoying great food. Live music featuring Kevin Mallory from 6-8pm

Live Music! Julie Mack Brazilian Jazz

Thursday, September 24 • 7 PM - 9 PM

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

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.

Annual Urban Winery GRAPE STOMP

Sunday, September 27 • 1 PM - 5 PM

Join us at our Annual Grape Stomp. You know you've always wanted to do this!

The Urban Winery of Silver Spring hosts our annual Grape Stomp. You know you've always wanted to do this! Bring your family and friends and join in the fun. Children under 10 years old and accompanied by a ticketed adult are free. Wine and food available for purchase.