Host Memorable Wine Events in Silver Spring, MD
Events At A Glance
- Saturday, August 16th - 7 – 9PM: Live Music! 909
- Sunday, August 17th - 5 – 8PM: Sip ‘n Paint Class
- Wednesday, August 20th - 5 – 9PM: Corks & Cars Show featuring Bruno Sound
- Thursday, August 21st - 7 - 9PM: Live Music – Jeff Weintraub
- Sunday, August 24th - 11AM - 1PM: Vino Vinyasa Wine & Yoga Class
- Saturday, August 30th · 7 - 9pm - Live Music - Spyros Koliavasilis and his Greek Rebetika Duo Melos
- Thursday, September 4th · 7 - 8:30pm - Live Music - Philip LoPiccolo- Acoustic
- Saturday, September 6th - 7 - 9PM: Live Music – Wendy and the Lost Boys
- Sunday, September 14th - 11AM - 1PM: Vino Vinyasa Wine & Yoga Class
- Wednesday, September 17th - 5 – 9PM: Corks & Cars Show featuring Live Music - Hat & Hair
- Thursday, September 18th - 7 - 9PM: Live Music – Jeff Weintraub
- Saturday, September 20th · 4 - 7pm - Annual Urban Winery GRAPE STOMP
- Saturday, September 20th - 7 - 9PM: Live Music – Red Castle Blues Band
- Sunday, September 21st - 5 - 7pm: Tasting Class : Riesling Wines
- Thursday, September 25th - 7 - 9PM: Live Music – Julie Mack
- Saturday, September 27th · 7 - 9pm - Live Music - Spyros Koliavasilis with Melos
- Sunday, September 28th - 5 – 8PM: Sip ‘n Paint Class
- Saturday, October 11th - 4-8PM: Fall Paniyiri, Live Music: Spyros Koliavasilis & Melos
Host Your Event at The Urban Winery in
Silver Spring, MD
Celebrate your memorable event at The Urban Winery—perfect for birthdays, anniversaries, bridal showers, corporate events, and more. Our urban space accommodates up to 80 guests and offers handcrafted wines, catering options, and a vibrant, unforgettable atmosphere. Book an appointment today to speak with our Event Coordinator!
The Urban Winery Calendar of Events
LIVE MUSIC! 909
Saturday, August 16
7 - 9pm
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!
Sip 'n Paint Class!
Sunday, Aug 17
5pm - 8pm
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.
Corks and Cars Show
Wednesday, August 20
5pm - 9pm
Corks and Cars Show featuring Bruno Sound! 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 listening to live music, featuring Bruno Sound. (Rain date August 27)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!
Jeff Weintraub
Thursday, August 21
7pm - 9pm
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.
Vino Vinyasa Wine and Yoga Class!
Sunday, August 24
11am - 1pm
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! Spyros Koliavasilis and his Greek Rebetika Duo Melos
Saturday, August 30
7pm - 9pm
Come listen to the velvety vocals of Spyros Koliavasilis - Maryland 2025 Heritage Award winner - and the smooth sounds of his Rebetiko duo, Melos. Melos performs Athenian style music, rebetiko (Greek blues), island music, entechno, and more.
LIVE MUSIC - Philip LoPiccolo- Acoustic
Thursday, September 4
7pm - 8:30pm
Join us for an unforgettable evening of wine, food, and music with Philip - a member of the Red Castle Blues Band which has been gigging with original songs and covers in the DMV for over a decade. Philip plays acoustic covers from the 1960s, 70’s and 80’s as soft background music.
LIVE MUSIC! Wendy and the Lost Boys
Saturday, September 6
7pm - 9pm
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 drum
Vino Vinyasa Wine and Yoga Class!
Sunday, September 14
11am - 1pm
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.
Corks and Cars Show with live music featuring Hat & Hair
Wednesday, September 17
5pm - 9pm
Corks and Cars Show featuring Hat & Hair! 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 listening to live music. Hat & Hair is an acoustic stringband based in Baltimore
LIVE MUSIC! Jeff Weintraub
Thursday, September 18
7pm - 9pm
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.
Annual Urban Winery GRAPE STOMP with Live Music to follow
Saturday, September 20
4pm - 7pm
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 and stay for some great live music starting at 7pm featuring the Red Castle Blues Band!
LIVE MUSIC! Red Castle Blues Band
Saturday, September 20
7 pm- 9pm
Join us for great wine and great live music! The Red Castle Blues Band was formed specifically to participate in the 2011 Smithsonian Folklife Festival Staff Picnic and has been gigging in the DMV area ever since. The band is influenced by the classic rocks sounds of the 1960’s and 1970’s and plays originals and rock and blues covers.
French Winer Dinner - 4 courses & wine pairings!
Sunday, September 21
5pm - 7pm
This gourmet dinner, prepared by a French chef will include 4 courses and wine pairings. Our Sommelier, Damon Callis, will be on hand to chat about the wines served along with the process & history of winemaking, and answer any wine related questions you may have. Taste. Learn. and Create new experiences here with us at The Urban Winery.
LIVE MUSIC!! Julie Mack Brazilian Jazz
Thursday, September 25
7pm - 9pm
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.
LIVE MUSIC - Spyros Koliavasilis with Melos - GREEK NIGHT
Saturday, September 27
7pm - 9pm
The duo offers a refined repertoire of Greek music that they have performed at prestigious venues including the Embassy of Greece and many music festivals. They deliver the sounds of traditional music from all around Greece in a festive and family-friendly atmosphere. Taste the wide array of wines and cocktails at Urban Winery and explore the Greek Night menu.
Sip 'n Paint Class!
Sunday, September 28
5pm - 8pm
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
Let’s paint, sip, and make memories together!
Fall Paniyiri with live music: Spyros Koliavasilis and Melos
Saturday, October 11
4 - 8pm
Join us for our family-friendly Fall Paniyiri — a celebration of Greek music, food, and wine! Enjoy the velvety vocals of Spyros Koliavasilis, Maryland’s 2025 Heritage Award winner, and his Rebetiko duo, Melos, known for their refined Greek repertoire. Savor wine, beer, and cocktails at Urban Winery, plus a special Greek menu featuring souvlaki, lamb, and more. Explore local art vendors and fun activities for kids.
The Urban Winery Calendar of Events
LIVE MUSIC! 909
Saturday, August 16
7 - 9pm
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!
Sip 'n Paint Class!
Sunday, Aug 17
5pm - 8pm
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.
Corks and Cars Show
Wednesday, August 20
5pm - 9pm
Corks and Cars Show featuring Bruno Sound! 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 listening to live music, featuring Bruno Sound. (Rain date August 27)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!
Jeff Weintraub
Thursday, August 21
7pm - 9pm
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.
Vino Vinyasa Wine and Yoga Class!
Sunday, August 24
11am - 1pm
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! Spyros Koliavasilis and his Greek Rebetika Duo Melos
Saturday, August 30
7pm - 9pm
Come listen to the velvety vocals of Spyros Koliavasilis - Maryland 2025 Heritage Award winner - and the smooth sounds of his Rebetiko duo, Melos. Melos performs Athenian style music, rebetiko (Greek blues), island music, entechno, and more.
LIVE MUSIC - Philip LoPiccolo- Acoustic
Thursday, September 4
7pm - 8:30pm
Join us for an unforgettable evening of wine, food, and music with Philip - a member of the Red Castle Blues Band which has been gigging with original songs and covers in the DMV for over a decade. Philip plays acoustic covers from the 1960s, 70’s and 80’s as soft background music.
LIVE MUSIC! Wendy and the Lost Boys
Saturday, September 6
7pm - 9pm
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 drum
Vino Vinyasa Wine and Yoga Class!
Sunday, September 14
11am - 1pm
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.
Corks and Cars Show with live music featuring Hat & Hair
Wednesday, September 17
5pm - 9pm
Corks and Cars Show featuring Hat & Hair! 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 listening to live music. Hat & Hair is an acoustic stringband based in Baltimore
LIVE MUSIC! Jeff Weintraub
Thursday, September 18
7pm - 9pm
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.
Annual Urban Winery GRAPE STOMP with Live Music to follow
Saturday, September 20
4pm - 7pm
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 and stay for some great live music starting at 7pm featuring the Red Castle Blues Band!
LIVE MUSIC! Red Castle Blues Band
Saturday, September 20
7 pm- 9pm
Join us for great wine and great live music! The Red Castle Blues Band was formed specifically to participate in the 2011 Smithsonian Folklife Festival Staff Picnic and has been gigging in the DMV area ever since. The band is influenced by the classic rocks sounds of the 1960’s and 1970’s and plays originals and rock and blues covers.
French Wine Dinner - 4 courses & wine pairings!
Sunday, September 21
5pm - 7pm
This gourmet dinner, prepared by a French chef will include 4 courses and wine pairings. Our Sommelier, Damon Callis, will be on hand to chat about the wines served along with the process & history of winemaking, and answer any wine related questions you may have. Taste. Learn. and Create new experiences here with us at The Urban Winery.
LIVE MUSIC!! Julie Mack Brazilian Jazz
Thursday, September 25
7pm - 9pm
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.
LIVE MUSIC - Spyros Koliavasilis with Melos - GREEK NIGHT
Saturday, September 27
7pm - 9pm
The duo offers a refined repertoire of Greek music that they have performed at prestigious venues including the Embassy of Greece and many music festivals. They deliver the sounds of traditional music from all around Greece in a festive and family-friendly atmosphere. Taste the wide array of wines and cocktails at Urban Winery and explore the Greek Night menu.
Sip 'n Paint Class!
Sunday, September 28
5pm - 8pm
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
Let’s paint, sip, and make memories together!
Fall Paniyiri with live music: Spyros Koliavasilis and Melos
Saturday, October 11
4 - 8pm
Join us for our family-friendly Fall Paniyiri — a celebration of Greek music, food, and wine! Enjoy the velvety vocals of Spyros Koliavasilis, Maryland’s 2025 Heritage Award winner, and his Rebetiko duo, Melos, known for their refined Greek repertoire. Savor wine, beer, and cocktails at Urban Winery, plus a special Greek menu featuring souvlaki, lamb, and more. Explore local art vendors and fun activities for kids.
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Reservations suggested for parties of 5 or more
