🎶 Live Music at Ollie’s Featuring Steven Reynolds

Saturday, November 8 • 8–10 PM • No Cover

Get ready to vibe, sway, and sing along—Steven Reynolds is bringing his soulful sound and magnetic energy to Ollie’s for one unforgettable night. Whether you're a die-hard fan or just discovering his smooth vocals and heartfelt lyrics, this is your chance to experience live music that hits you right in the feels.

🎵 Live at Ollie’s: Next of Kin

Wednesday, November 7 • 7–9 PM • No Cover

Join us for an evening of heartfelt harmonies and timeless tunes with Next of Kin, an acoustic father/daughter-in-law duo bringing country-western charm and classic favorites to life. Their easygoing style and genuine connection make for a cozy, toe-tapping night you won’t want to miss.

Whether you're here for the music, the whiskey, or just good company—this is the kind of show that feels like home.

Comedy Nights

Join us on the first Thursday of each month from September - December for great jokes, great drinks, and great pizza!

What more do you need?

🎤 Laugh with local comedians 🍷 Sip your favorite wine or whiskey 🍕 Enjoy our delicious pizza deal

Jazz by Candlelight

Featuring Andrea Lewis on Saxophone

Saturday, November 1st - 8PM - 9PM

Join us for a relaxing evening of jazz music, wine, and dessert

Cost $25 per person**

**One glass of wine and dessert included

Join us for a Spooktacular Party!

Costume Contest, Drinks, Snacks & Live Music

🎃 Ollie’s Joins the Goblin Walk

Halloween Night • 4–6 PM • No Tricks, Just Treats

Ollie’s Wine & Whiskey Bar is proud to be part of Silverton’s beloved Goblin Walk—a safe, spirited way for kids to trick-or-treat around town. From 4 to 6 PM on Halloween night, we’ll be handing out treats to all the little goblins, ghouls, superheroes, and storybook royalty who stop by.

Look for the Goblin Walk pumpkin sign in our window to know we’re ready with goodies and grins!

Whether you're tiny and costumed or just young at heart, Ollie’s is here to make your Halloween magical.

SOLD OUT SIP & CINEMA

Join us for a cozy movie night featuring Hocus Pocus on the big screen, complete with themed cocktails or mocktail and gourmet popcorn.

Cost $15 per person doors open at 6:30pm.

Price includes:

Popcorn: Witch’s Brew – purple/green/orange candy-coated with cinnamon.
Cocktail: Black Flame Martini – Blackberry vodka, cranberry juice, black sugar rim.
Mocktail: Potion Pop – Grape juice, orange soda, splash of lime.

Duo Night at Ollie’s

True North Duo
Americana-Bluegrass String Magic • No Cover

Join us for an intimate evening of harmony and heartstrings as Kristen Grainger & True North bring their crowd-winning Americana-bluegrass sound to Ollie’s. This duo performance blends poetic lyrics, lush vocals, and masterful string work—perfect for a night of wine, whiskey, and wonder.

Date: 10/18/25
Time: 7-9pm
Location: Ollie’s Wine & Whiskey Bar, Silverton, OR

No cover. Just soul-stirring music and the kind of atmosphere that makes you feel right at home.

D.Y.A.O. All-Request Dance Party

and Line Dance Lessons

🎶 Comedy & Music at Ollie’s

Featuring: Joe Stoddard

Get ready for a night of laughter, live music, and laid-back charm at Ollie’s. Joe Stoddard brings the perfect blend of comedy and acoustic flair—think witty storytelling meets toe-tapping tunes. Whether you're sipping whiskey or swirling wine, this is your midweek reset with soul and sass.

📅 Date: 10/10/25
🕗 Time: 7-9pm
📍 Location: Ollie’s Wine & Whiskey Bar, Silverton, OR

No cover. No pretense. Just good people, great drinks, and unforgettable entertainment.

🎶 Live Music at Ollie’s

Featuring Thunder Road

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🎶 Live Music at Ollie’s

Featuring Don Edwards

From hard rock riffs to heartfelt acoustic ballads, Don has been sharing his passion for guitar and songwriting since he was a teen. After years of recording, performing, and collaborating with incredible musicians, he’s just released his latest project: Don plays every instrument, sings every vocal, and handled all the recording, mixing, and mastering himself true independent artistry at its finest.

🎶 Live Music at Ollie’s

Featuring UNCLE DJ

Kick back, sip something delicious, and let the music set the mood. Uncle DJ brings a unique blend of live acoustic guitar and soulful vocals, weaving together crowd‑pleasing classics, modern hits, and a few surprises along the way. His easygoing style and warm stage presence make every performance feel like you’re hanging out with an old friend—one who just happens to have a killer playlist.

SIP & CINEMA

Join us for a cozy movie night featuring Mamma Mia 2 on the big screen, complete with themed cocktails and gourmet popcorn.

Cost $15 per person doors open at 6:30pm.

Price includes:

Popcorn: Dancing Queen – caramel, dried cherries, almonds.
Cocktail: Cherry Disco Sangria – Red wine, cherry liqueur, citrus, sparkling water.
Mocktail: Shirley Disco – Sparkling cherry juice, orange slices, soda water.