Live Music! Fast Eddie & The Slowpokes

Friday, May 1st - 7 - 9 PM

Fast Eddie & The Slowpokes are guaranteed to get you up on your feet! The Slowpokes playlist is inspired by classic blues material.

Join us at The Urban Winery to hear Fast Eddie & The Slowpokes blues playlist, inspired by classic blues material from Chicago to West Coast Swing, Motown to Muscle Shoals, and all the rock n’ roll in between.

Live Music! Jazz by the Glen Echoes

Saturday, May 2nd - 7 - 9 PM

The Urban Winery hosts Jazz by the Glen Echoes - a vestigial five-piece jazz combo

Jazz by The Glen Echoes features Mike Jolkovsky, Chuck Ciorba,

Marius Pruessner, Mike Morrison, and Boyce Thompson -- performing

reimagined standards, noteworthy novelties, and the begrudging original.

MAHJONG LEARNING SERIES

Sunday, May 3rd - 2 PM - 4 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!

Dates & Times (classes are approximately 2.5 hours, each):

Tuesday, 5/3 @ 2:00pm - 4:00p

Tuesday 5/10 @ 2:00pm - 4:00pm

Tuesday 5/17 @ 2:00pm - 4:00pm

(Two lessons recommended, with a third session of guided play. Contact certified American Mahjong instructor, Kerrianne Rejevich for lesson details & pricing - letsmahj.dmv@gmail.com or DM @LetsMahjDMV on IG)

Live Music! Beyhan

Friday, May 8th - 7 - 9 PM

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! Freddie Long

Saturday, May 9th - 7 - 9 PM

Get ready for an awesome night at THE URBAN WINERY with the talented Freddie Long performing live! Join us on May 9, 2026 at 7:00 PM (Eastern Time) for great vibes, good tunes, and a relaxed atmosphere. Whether you're a longtime fan or just looking for a fun evening out, this is the place to be. Bring your friends and enjoy some fantastic live music in person

Cupcake Making Workshop Mother's Day Special Event

Sunday, May 10th, 2 - 3:30 PM

Please join us and Karissa from Sweet Dreams to make cupcakes! Bring your moms, bring your kids! 5 cupcakes to enjoy - onsite and to bring home. You will be guided in making your cupcakes and a variety of flavors will be offered for you to choose from. And of course, you can order drinks (we offer mocktails too) while you decorate! Kids welcome (ages 5+) between 5-12 are free. Please note we need a minimum of 12 participants (registered a week prior) and if we don't hit this minimum, will need to cancel/reschedule.

Sip n’ Play SnapKu at our SnapKu Game Night!

Wednesday, May 13th - 6:30 - 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! Julie Mack Brazilian Jazz

Thursday, May 14th - 7 - 9 PM

With Julie’s rich, velvety voice and the band’s infectious energy and top-tier musicianship, this will be an unforgettable evening. Whether you're a jazz lover or just looking to enjoy a relaxing night with great wine, speciality Brazilian cocktails and food, and amazing music, this event is not to be missed. Sip, sway, and immerse yourself in the vibrant rhythms of Brazil—right here at The Urban Winery.

Live Music! Evelyn Acht

Saturday, May 16th - 7 - 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.

Sip 'n Paint Class!

Sunday, May 17th - 5 - 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!

Corks and Cars Show with live music

Wednesday, May 20th - 5-9 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 Rock, Salt and Grass from 5-8pm. 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.

Live Music! Jeff Weintraub

Thursday, May 21st - 7-9 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! That 80's Synthpop Band

Friday, May 22nd - 7-9 PM

That 80s Synthpop Band brings the nostalgia with favorites synth/alt tunes from the 80s, including songs by Depeche Mode, Duran Duran, and Flock of Seagulls. Get ready to sing and dance while reminiscing about Friday Night Videos, the Walkman, neon clothes, and asymmetrical haircuts.

Crepes and Bubbles

Sunday, May 24th - 12 PM - 3 PM

Join us and The Crepe Factory for a variety of crepes and bottomless mimosas!

The Crepe Factory will be on hand making you a variety of delicious crepes and enjoy bottomless mimosas while you enjoy this unique brunch!

Live Music! Cole Larravide

Friday, May 29th - 7-9 PM

Cole Larravide is a Maryland-based singer/songwriter. He has performed at many world-famous venues including Blues Alley (DC), The Cavern Club (Liverpool), Whisky A Go Go (LA), The Fillmore (Silver Spring), The Birchmere (Alexandira), The Hamilton Live (DC), and The Cobblestone (Dublin). Cole has also performed as an opening act for Three Dog Night, Grand Funk Railroad, Tommy James & The Shondells, Ruthie Foster, 10cc, Gary Puckett & The Union Gap, Hot 8 Brass Band, and The Beatles original drummer Pete Best. He recently recorded an upcoming album at Muscle Shoals Sound Studio.

Live Music! Bell Lipton Trevey Band

Saturday, May 30th - 7-9 PM

Bell Lipton Trevey present their music in the stripped-down style of “MTV Unplugged.” Comprised of players from the Springfield, VA based band Gotcha Covered, they cover classic rock, pop, Motown, alternative, blues, and country sounds from across the decades for audiences of all ages. They blend our voices with acoustic and electric guitars, keyboard, saxophone, banjo, and harmonica.

Vino Vinyasa Wine and Yoga Class!

Sunday, May 31st - 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!