Upcoming Events
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Upcoming Events *
Hours: Wednesday - Saturday 4-10pm
Ollie's Birthday!!
Ollie’s Wine & Whiskey Bar Turns ONE!
Join us as we celebrate Ollie’s 1st Birthday with a full day of great drinks, great company, and a toast to an amazing first year!
All-Day Birthday Celebration
Stop in anytime throughout the day to celebrate with us! We’ll be raising a glass to one incredible year with the community that made it all possible.
🍷 Mix & Mingle – 5:30 PM
Join us in the evening for a special Mix & Mingle starting at 5:30 PM. It’s the perfect chance to connect with friends, meet fellow wine and whiskey lovers, and celebrate together in true Ollie’s style.
Expect:
Curated wine and whiskey selections
A relaxed, social atmosphere
Birthday cheers and good vibes all evening
Whether you’ve been with us since day one or it’s your first visit, we’d love to celebrate with you. Come raise a glass and help us kick off year two! 🥂
Stay tuned for more details and surprises.
Cheers to one amazing year — and many more to come!
LIVE MUSIC - The Vast Majority
The Vast Majority - Featuring Terry and Leslee Bay
NO COVER CHARGE
Silverton Rotary Evening Meeting
Silverton Rotary Evening Meeting
Join members and guests for the Silverton Rotary Evening Meeting, a great opportunity to connect with fellow professionals, community leaders, and friends in a relaxed and welcoming setting.
Enjoy meaningful conversation, community updates, and the chance to learn more about the projects and initiatives that support and strengthen the Silverton community.
Guests and prospective members are always welcome. Come mix, mingle, and discover how Rotary continues to make a positive impact locally and around the world.
We look forward to seeing you there!
DYAO - Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
Tequila Academy
$25 at the door w/Patron Spirits
Join us for an evening of discovery and flavor as we dive into the world of tequila with Patrón Tequila. This guided tasting experience will explore how tequila is crafted—from the harvesting of blue agave to the art of distillation and aging.
Guests will sample a curated lineup of Patrón tequilas while learning about the unique characteristics of each expression, how terroir and production methods influence flavor, and the best ways to taste and appreciate premium tequila.
Along the way, enjoy expertly crafted cocktails, tasting notes, and fun insights that will deepen your appreciation for this iconic spirit.
Perfect for tequila lovers and curious beginners alike, Tequila Academy is equal parts education, tasting, and a great night out.
Live Music - Steven Reynolds
🎶 Live Music at Ollie’s Featuring Steven Reynolds
Saturday, May 2 • 7–9 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.
DYAO - Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
Live Music - Uncle DJ
🎶 Live Music at Ollie’s
UNCLE DJ - Featuring Yurly Murashko NO COVER
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.
Mix & Mingle Night
Join us for Ollie’s Mix & Mingle an evening designed for good conversation, comfortable vibes, and meeting great people in your age group. Easy introductions, Comfy seating, warm lighting, Delicious cocktails + mocktails
Music at a volume where you can actually talk.
Simple conversation starters all around
Pet Crawl
Ollie’s Wine & Whiskey Bar – Pet Celebration
Join us at Ollie’s for a tail‑wagging good time
We’re opening early and rolling out special treats for pets and humans alike.
🐶 Pet Crawl – Early Opening at 11 AM
Kick off the day with your furry friends. Grab a drink, mingle with fellow pet lovers, and enjoy the festive atmosphere.
🍷 FREE Wine Tasting – 4 PM to 6 PM
Featuring Cubanisimo Winery. Sample a curated selection of their wines and discover new favorites.
🐕🦺 FREE Pup Shakes
Because the pups deserve something special too. Fresh, pet‑safe, and delicious.
Sip & Cinema - TOP GUN
SIP & CINEMA
Join us for a cozy movie night featuring Top Gun 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
Cocktail
Mocktail
DYAO - Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
DYAO - Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
Lexi Tucker - LIVE
$15 tickets advance purchase only
Lexi Tucker is a singer/songwriter from Silverton, Oregon, whose roots run deep in country music. Born and raised in the countryside, Lexi grew up surrounded by the sounds of classic country legends and began singing as a little girl. Her heartfelt lyrics and soulful voice reflect her upbringing and love for storytelling through song.
Now writing and performing her own original country music, Lexi brings authenticity and charm to every performance. Her songs capture the spirit of small-town life, love, and the open road — all delivered with a voice that feels both nostalgic and fresh.
Join us at Ollie’s for an unforgettable evening of live country music with Lexi Tucker. Sip your favorite wine or whiskey, relax, and enjoy the warm, down-home vibes that make Lexi’s shows so special.
❤️ Don’t Miss It
Come celebrate community, music, and good spirits at Ollie’s. Whether you’re a country fan or just looking for a great night out, Lexi Tucker’s live performance will make you feel right at home.
Buy Ticket
DYAO - Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
DYAO - Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
Silverton Rotary Evening Meeting
Silverton Rotary Evening Meeting
Join members and guests for the Silverton Rotary Evening Meeting, a great opportunity to connect with fellow professionals, community leaders, and friends in a relaxed and welcoming setting.
Enjoy meaningful conversation, community updates, and the chance to learn more about the projects and initiatives that support and strengthen the Silverton community.
Guests and prospective members are always welcome. Come mix, mingle, and discover how Rotary continues to make a positive impact locally and around the world.
We look forward to seeing you there!
TICKETED EVENT - Winemaker’s Dinner
Winemaker’s Dinner with heaVin Estate Vineyards
Join us at Ollie’s for an unforgettable evening celebrating the craft of exceptional food, wine, and music. This exclusive ticketed event features a five‑course chef‑curated dinner, each dish thoughtfully paired with Estate wines from heaVin Estate Vineyards.
Throughout the evening, enjoy the warm ambiance of live jazz, featuring Carter Doud creating the perfect backdrop for a refined and memorable dining experience.
A limited number of seats are available. Reserve your place at the table and savor a night of culinary artistry and world‑class winemaking.
$95 per person Tickets Required
**Max’s is closed for a private event
DYAO Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
LIVE MUSIC - Melody Jordan
With warm acoustic guitar, expressive vocals, and storytelling lyrics, Melody creates the perfect soundtrack for bold pours, cozy vibes, and meaningful connection in the heart of downtown Silverton.
NO COVER CHARGE
LIVE MUSIC - Jody Carroll
Jody Carroll is a blues & Roots performer and songwriter who effortlessly creates bold interpretations of old Blues and American Folk music, his own songs, stories and improvisational
NO COVER CHARGE
Grease the Movie
$15 per person
Join us for Sip & Cinema in March as Greased Lightning is rolling in on the big screen! Grab your besties, sip something delicious, and sing along to the one and only Grease!
**Max's Hideaway is SOLD OUT only upstairs seating available $15 includes a "Pink Lady" or "Greased Lightning" unless you are feeling a mocktail then the "Hopelessly Devoted" is for you! Unlimited popcorn ALWAYS!
Mix & Mingle Night
Join us for Ollie’s Mix & Mingle an evening designed for good conversation, comfortable vibes, and meeting great people in your age group. Easy introductions, Comfy seating, warm lighting, Delicious cocktails + mocktails
Music at a volume where you can actually talk.
Simple conversation starters all around
LIVE MUSIC - Lane Norberg
Lane Norberg is a singer-songwriter from Portland, OR. Norberg's indie-folk sound has been described as "James Taylor meets John Mayer", and he has a knack for writing a killer love song.
DYAO Line Dancing
2nd & 4th Fridays
Lessons @ 7:30 PM & 8:30 PM
**two drink minimum requested
DYAO Line Dancing
Lessons @ 7:30 PM & 8:30 PM
2nd & 4th Friday’s
**two drink minimum requested
Ugly Sweater Party
Ollie’s Ugly Sweater Party
Celebrate the season with a little irreverence and a lot of soul. On Saturday, December 20th, Ollie’s Wine & Whiskey Bar invites you to don your most outrageous holiday knitwear and enjoy an evening of live music.
Expect festive cocktails, whiskey warmth, and a crowd that knows how to party — even in pom-poms and reindeer prints.
Sip & Cinema - White Christmas
SIP & CINEMA
Join us for a cozy movie night featuring White Christmas 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: Snowfall Crunch – white chocolate, peppermint, coconut flakes.
Cocktail: Holiday Snowcap – Peppermint schnapps, white chocolate liqueur, cream.
Mocktail: Frosty Peppermint Cocoa – White hot chocolate with crushed candy cane.
A Christmas Carol
A Christmas Carol by Charles Dickens like you have never seen before.
Adapted by Silverton's own Doug Ousterhout
Step back to 1843 as longtime theater teacher Doug Ousterhout (Mr. O) brings this holiday classic to life in a one-man adaptation of A Christmas Carol.
Stage 207 will be transformed into a dark, immersive world where every candle flicker and ghostly whisper pulls you deeper into Scrooge’s journey.
Your reserved ticket includes three themed cocktails (or mocktails):
• The Scrooge Sour
• The Ghost of Christmas Past
• The Tiny Tim Toddy
Join us for an unforgettable evening of storytelling, spirits, and seasonal magic.
Comedy & Music
🎶 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: 12/5/25
🕗 Time: 7-9pm
📍 Location: Ollie’s Wine & Whiskey Bar, Silverton, OR
No cover. No pretense. Just good people, great drinks, and unforgettable entertainment.
Comedy Nights
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
Oregon Ducks Football Watch Party
🍹Game-day drink deals
🏈 The Oregon Ducks on the BIG screen
So rally your crew, wear your GREEN, and let’s turn Ollie’s into a sea of feathers and football fever.
Because game day is better with good food, great drinks, and a whole lotta quack!
Oregon Ducks Watch Party at Ollie’s
Join us at Ollie’s Wine & Whiskey Bar on Saturday, November 29th at 4PM to cheer on the Oregon Ducks as they take on the Washington Huskies in one of the season’s biggest matchups. We’re turning up the volume, pouring the good stuff, and rallying the flock for a game-day celebration full of spirit and camaraderie.
Whether you’re a lifelong fan or just here for the vibes, Ollie’s is the place to be. - just bring your game face and your Duck pride.
Saturday, November 29 • 4PM Kickoff
Sip & Cinema - Mean Girls
SIP & CINEMA
Join us for a cozy movie night featuring MEAN GIRLS 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: On Wednesdays We Eat Pink Popcorn – strawberry or cotton candy popcorn with white chocolate drizzle.
Cocktail: Burn Book Cosmo – Vodka, cranberry, lime, splash of pink lemonade.
Mocktail: Pink Regina – Pink lemonade with soda water + strawberry garnish.
Live Music - Steven Reynolds
🎶 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.
Wine Tasting Murder Mystery
An elite gathering. Fine wine. Decadent cheese. And somewhere between the toasts and the laughter… a murder. Step into the shadows of the Chateau des Falles for a night of intrigue, indulgence, and whodunit you’ll never forget.