Celebrate a Year of Wine, Music, and Milestones

2025 is shaping up to be an unforgettable year at Sweet Cheeks Winery! With a lineup of events that blends the best of wine, food, music, and celebrations, there’s something for everyone to enjoy. Whether you’re a wine enthusiast, a loyal club member, or visiting for the first time, our events are crafted to bring people together and create lasting memories.

Here’s your complete guide to all the incredible events we have planned. Mark your calendar and join us for an exciting year at Sweet Cheeks Winery!

April 13 – Mimosas & Matrimony Wedding Showcase

Time: 10:00 AM – 4:00 PM

Details: Planning your dream wedding? Join us for our third annual boutique wedding showcase, co-hosted with Event Crush and Destination Events. Sip on mimosas while exploring our beautiful venue and connecting with talented vendors who can bring your vision to life.

Highlights:

  • Live music
  • Swag bags for the first 50 couples
  • Raffles, light bites, desserts, and couple portraits in the vineyard
  • Food trucks and dessert booths available from 12:00 PM – 4:00 PM

Tickets: $10 pre-purchase | $15 at the door

Buy Tickets

May 10-11 – Mother’s Day Weekend

Time: 11:00 AM – 6:00 PM

Details: Celebrate Mother’s Day with wine, music, and family fun! Treat mom to a day at the vineyard with tasting stations, live music from Storm Tipton, and kid-friendly activities sponsored by Nurturely.

Highlights:

  • Live music: Storm Tipton (12:00-2:00 PM, 2:30-4:30 PM)
  • Oregon Wood Fired Pizza available for purchase
Make a Reservation

May 24-26 – Memorial Day Weekend

Time: 11:00 AM – 6:00 PM

Details: Kick off summer with a weekend of wine, live music, and exclusive discounts! Whether you’re stocking up on your favorites or sipping on our newest releases, this weekend is all about enjoying the vineyard vibes.

Highlights:

  • Live music: Storm Tipton (12:00-2:00 PM, 2:30-4:30 PM)
  • Oregon Wood Fired Pizza available for purchase
    • Discounts:10% off 4+ bottles for consumers
    • 25% off 4+ bottles for wine club members
    • Free FedEx Ground shipping on 6+ bottles
Make a Reservation

June 14 – Summer Concert Series: The Talbott Brothers

Time: 6:00 PM – 9:00 PM

Details: Enjoy an evening of soulful Americana music with The Talbott Brothers. Grab a glass of your favorite wine, settle in under our iconic oak tree, and let the music transport you.

Tickets: $35 per person

Buy Tickets

June 29 – Summer Club Release Pickup Party (Club-Exclusive Event)

Time: 11:00 AM – 6:00 PM

Details: Celebrate the summer wine release with fellow club members! This exclusive event features tastings of our newest releases paired with curated bites.

Tickets will be available at a later date

July 5 – Summer Concert Series: Haley Johnsen

Time: 6:00 PM – 9:00 PM

Details: Oregon’s own Haley Johnsen brings her unique blend of Americana and Alt-Pop to Sweet Cheeks. Don’t miss this unforgettable evening of live music, delicious wine, and good vibes.

Tickets: $35 per person

Buy Tickets

August 9 – Summer Concert Series: Irie Love

Time: 6:00 PM – 9:00 PM

Details: Feel the island vibes with Irie Love’s soulful reggae tunes. Gather your friends and enjoy a summer night under the stars with great music and wine.

Tickets: $35 per person

Buy Tickets

August 30 – September 1 – Labor Day Weekend

Time: 11:00 AM – 6:00 PM

Details: Wrap up summer with a relaxing weekend at the winery! Enjoy live music, food, and your favorite Sweet Cheeks wines.

Highlights:

  • Live music: Storm Tipton (12:00-2:00 PM, 2:30-4:30 PM)
  • Food by MBOSQ available for purchase
Make a Reservation

September 19 – Club-Exclusive 20th Celebration Event (Club-Exclusive Event)

Time: 11:00 AM – 6:00 PM

Details: We’re celebrating 20 amazing years of Sweet Cheeks Winery with an exclusive event just for our wine club members. Enjoy live music, delicious food, and, of course, wine!

Highlights:

  • Live music: Teresa Cunningham Band
Make a Reservation

September 20-21 – 20th Anniversary Celebration

Time: 11:00 AM – 6:00 PM

Details: It’s time to celebrate 20 years of Sweet Cheeks Winery! Join us for a weekend-long party featuring wine specials, live music, games, and more. Let’s toast to the memories we’ve made and the exciting future ahead.

Make a Reservation

Plan Your Year with Sweet Cheeks Winery

2025 is a year you won’t want to miss at Sweet Cheeks Winery. From exclusive wine club events to public celebrations, our calendar is packed with opportunities to sip, savor, and celebrate.

Be sure to RSVP or purchase tickets early—many events sell out quickly!

Let’s make 2025 a year to remember. We can’t wait to raise a glass with you!