Woudstra Market Food Truck 8.7.2025
2025-08-07 16:00 - 20:00 (America/Chicago) | Oscar Carl Vineyard, 1473 Buchanan Ave, Sioux City, IA, 51106, United States
This amazing Food Truck from Orange City, Iowa, specializes in BBQ pulled pork, brisket, mac & cheese, bratwurst, and the most amazing loaded baked potatoes!!! (Pronounced WOW-d-stra – you’ll be saying Wow! What great food!)

Heartland Coffee & Nosh 8.14.2025
2025-08-14 16:00 - 20:00
We love it when Heartland Coffee & Nosh comes to Oscar Carl! They’ve always got something great that pairs perfectly with our wines!

Pickled Palette Paint & Sip 8.20.2025
2025-08-20 18:00 - 20:00
We’re excited to host Pickled Palette for another fun Paint & Sip in the creative setting of our lower level Vineyard View! For more info and tickets, click here. (Contact Pickled Palette at 712.224.2757 with any ticket questions.)
Easy-peasy parking on our lower level. Just follow the road between the split-rail fence and the gray building, curve around and you’ll arrive at your destination. You’ll be able to order wine and other beverages, along with our selection of food at the main floor bar. Or you can bring your own snacks. Be ready to have some fun and let your creativity flow!

SMASH Food Trailer 8.21.2025
2025-08-21 16:00 - 20:00
SMASH by Chef Clay – an experience to experience!!

Heartland Coffee & Nosh 8.28.2025
2025-08-28 16:00 - 20:00

Heartland Coffee & Nosh 9.4.2025
2025-09-04 16:00 - 20:00

Heartland Coffee & Nosh 9.11.2025
2025-09-11 16:00 - 20:00
We love it when Heartland Coffee & Nosh comes to Oscar Carl! Especially 3 weeks in a row!! They’ve always got something great that pairs perfectly with our wines!

SMASH Food Trailer 9.18.2025
2025-09-18 16:00 - 20:00

Chazz's Smoke Shack 9.25.2025
2025-09-25 16:00 - 20:00
Holy Smoke! We’re excited to host this award-winning BBQ team! What wine will you pair with your choice? Small Town BBQ, Big Time Flavor! Old fashioned stick burned BBQ. Come and getcha some!

Pickled Palette Paint & Sip 10.22.2025
2025-10-22 18:00 - 20:00

Big Daddy Trivia Night 11.17.2025
2025-11-17 17:30 - 19:00

Pickled Palette Paint & Sip 11.19.2025
2025-11-19 18:00 - 20:00

Big Daddy Trivia Night 11.24.2025
2025-11-24 17:30 - 19:00

Lighting of the Christmas Tree *Rescheduled* to 11.30.2025 at 1:30pm
2025-11-30 13:30 - 14:00
It’s beginning to feel a bit like Christmas!! Our 12-ft tall pencil Christmas Tree has become a popular spot for holiday photos for friends and family. Start your own tradition today! We’ll have some special holiday treats and even a visit from “Oscar” and “Carl” all decked out for the holidays, We’ll tell the story of the tree and turn the lights on at 1:30pm. Come join us for some good old fashioned holiday cheer! Cheers to Christmas!

Big Daddy Trivia Night 12.1.2025
2025-12-01 17:30 - 19:00

Big Daddy Trivia Night 12.8.2025
2025-12-08 17:30 - 19:00

Big Daddy Trivia Night 12.15.2025
2025-12-15 17:30 - 19:00

Pickled Palette Paint & Sip 12.17.2025
2025-12-17 18:00 - 20:00
We’re excited to host Pickled Palette for another fun Paint & Sip in the creative setting of our lower level Vineyard View! For more info and tickets, click here. (Contact Pickled Palette at 712.224.2757 with any ticket questions.)
Easy-peasy parking on our lower level. Just follow the road between the split-rail fence and the gray building, curve around and you’ll arrive at your destination. You’ll be able to order wine and other beverages, along with our fabulous selection of food at the main floor bar. Or you can bring your own snacks. Be ready to have some fun and let your creativity flow!

Permanent Jewelry Pop-Up by Jaci's Jewelry
2025-12-20 13:00 - 16:00

Big Daddy Trivia Night 12.22.2025
2025-12-22 17:30 - 19:00

Big Daddy Trivia Night 12.29.2025
2025-12-29 17:30 - 19:00

Big Daddy Trivia 2.5.2026
2026-02-05 18:00 - 19:30

New Stage Players Presents: "A Taste for Wine & Murder!" 2.6.2026
2026-02-06 19:00 - 21:00
Click here for tickets!

*Sold Out* Graze - A Charcuterie Company Presents: "Galentine's Sip & Savor 2.10.2026
2026-02-10 17:30 - 19:30
**Sold Out**

Galentine's Paint & Sip with Pickled Palette 2.11.2026
2026-02-11 18:00 - 20:00

Big Daddy Trivia 2.12.2026
2026-02-12 18:00 - 19:30

Galentine's Shimmer & Soul Social 2.13.2026 **CANCELLED**
2026-02-13 18:00 - 20:00
Galentine’s Shimmer & Soul Social **CANCELLED**
Forget the superstitions of Friday the 13th—we’re reclaiming the night for a different kind of glow. This Galentine’s, join us for The Shimmer & Soul Social, an evening dedicated to the Spark of Friendship – a celebration of those rare women who bring light into our darkest days and turn the ordinary into something brilliant just by being there.
When you arrive and enter the cozy Galentine-ready Vineyard View, you’ll choose your first glass of one of our signature wines, your Keepsake Stir Stick, and your own Shaker of Edible Glitter. Throughout the night, we’ll guide you through “The Three Stirs”—intentional moments to swirl luster dust into your glass, creating a shimmering glow while you “stir up” the stories and shared history that keep your inner circle bright.
At 7:00 PM, the room will dim for a candlelit reading of our Shimmer Script: The Spark of a Familiar Friend, followed by a room-wide collective stir to celebrate the women who keep our fires burning.
Your Ticket Includes:

✨ Two Shimmering Pours: Oscar Carl Vineyard award-winning wine enhanced with your choice of edible luster dust.
🪄 The Keepsake: A Galentine’s Stir Stick to take home.
🧂 The Home Magic: A portable shaker of edible luster glitter to keep your future pours bright.
🧀 The Galentine’s Grazing Box: A curated spread featuring sweet and savory charcuterie, edible chocolate-chunk cookie dough, topped with a lovely pansy blossom.
📖 The Shimmer Script: A high-quality printed copy of our tribute to friendship.

(Wine Club members save $5/ticket with discount code “LeoJamesWineClub”)

Valentine's Day Romantic 3-Course Italian Dinner *SOLD OUT* at Oscar Carl Vineyard
2026-02-14 18:00 - 20:00
Experience the romance of a 3-course Italian dinner paired with wine for you and your sweetheart in the cozy Vineyard View of Oscar Carl.
Experience the transformation of Oscar Carl’s lower level Vineyard View into a romantic Italian bistro, complete with candlelight and tablecloths, Chiavari chairs, and classic violin music. A fresh Italian meal served to your table, where you and your sweetheart are seated, looking lovingly into each other’s eyes. Cheers to love, good food and great wine!
When you arrive and are escorted to your table, you’ll choose your wine – 2 glasses, a flight, or a bottle to share with your sweetheart.* (Beer, spirits or N/A substitutions are available.) Choose between marinara with meatballs and pasta or chicken fettucine alfredo, prepared and served by Aggie’s amazing team. Each meal comes with an Italian garden salad and garlic breadsticks, and finishes with a decadent Italian dessert – tiramisu. Bene!
If you are attending with other couples, just message or call so we can seat you as you prefer. Tables for 2, 4, or 6 are available.
*Each ticket is for one meal, plus 2 glasses of wine or a flight. “Bottle to share” is perfect if you and your sweetheart like the same wine. (If you don’t drink it all, you can take the rest home with you in a sealed bag.) One bottle is equivalent to 4 glasses, so a bottle serves 2 tickets.
(Leo James Wine Club members enter promo code “LeoJamesWineClub” to save $5/ticket!)
Click here for tickets and more information. Cheers!

Big Daddy Trivia 2.19.2026
2026-02-19 18:00 - 19:30

Siouxland GO Presents: Wine Tasting Social 2.19.2026
2026-02-19 18:00 - 19:30
Join Siouxland GO for their February Social at Oscar Carl Vineyard for a guided six wine tasting with education on each selection. Light meat and cheese pairings will be provided.
This is a great opportunity to connect with other professionals and enjoy a relaxed evening in a unique local setting.
$10 per person at the door ($5 for SGO members)
