Big Napa Energy in a Cowboy Hat
Town Square · Jackson · Steak House · Visit Website ↗
Reviewed by the RagingWine Tasting Desk · May 1, 2026
RagingWine reviewed The Million Dollar Cowboy Steakhouse’s wine list and gave it The Reliable — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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Wingman Metrics
You walk in past saddle bar stools and cowboy memorabilia and the wine list lands in your hands like a greatest hits album of Napa Valley. It's confident, unapologetic, and completely on-brand for a place called the Million Dollar Cowboy Steakhouse. This is not a list that wants to surprise you — it wants to satisfy you.
The list sits in the 150-250 bottle range and leans hard into California, particularly Napa Cabernet Sauvignon, which makes total sense when the menu is anchored by prime ribeyes and a bison tenderloin. You've got the usual suspects — Caymus, Silver Oak, Jordan, Stag's Leap, Far Niente — all solid producers, all well-chosen for the steakhouse context. Duckhorn Merlot shows up as a nod to those who aren't all-in on Cab, and Cakebread Chardonnay handles the white wine corner reasonably well. What's missing is any real depth outside California: no serious Burgundy, no Rhône, no Barolo to break the pattern — but that's a stylistic choice, not an oversight, and at least they own it.
The by-the-glass program runs 12-20 options, which is respectable for a steakhouse in a mountain tourist town. Expect the pours to skew heavily toward California reds with a Chardonnay or two rounding things out. There's no visible rotation or seasonal swap happening here — what you see is what you get, night after night.
Jordan Cabernet Sauvignon — $50-$70 (bottle est.)
Jordan consistently punches above its price point — elegant, structured, and built for red meat without demanding the triple-digit price tag that Opus One will. It's the smart move on this list.
Duckhorn Merlot
Everyone at a steakhouse is reaching for Cabernet, which means Duckhorn's Merlot gets overlooked. It's plush, serious, and frankly a better fit for the filet mignon than a tannic Cab would be.
Opus One
At $300+ in a restaurant, Opus One is nearly always a markup victim, and this list is no exception. It's a great wine — you can get it cheaper at a retail shop and drink it at home. Here, you're paying for the name on a big night out.
Stag's Leap Wine Cellars Cabernet Sauvignon + Cowboy Bone-In Ribeye
Stag's Leap brings enough structure and dark fruit to stand up to a big bone-in cut without steamrolling the beef. It's classic Napa doing exactly what Napa was born to do.
✔️ The Bottom Line
The Million Dollar Cowboy Steakhouse has a sommelier, a Wine Spectator credential, and a list that knows its audience — which is Jackson tourists who want great steak and great Napa Cab, full stop. Send a friend here if they want a proper California red with a serious piece of beef; just warn them to skip Opus One and let Jordan do the work.
Jackson · Jackson · Canadian, French
Wild Sage is a genuinely surprising wine destination for Jackson — a lodge-dining room that earns its Wine Spectator badge with France and California depth that few mountain-town restaurants bother to build. Prices trend high, but if you're already eating here, lean into the Burgundy section and let the fireplace do the rest.
Solid Range
Steep
Basic Stemmed
Willing but Green
Set & Forget
Proper
Jackson · Jackson · Italian
Glorietta is doing something genuinely uncommon for a mountain resort town: running a focused, Italy-first wine program that actually earns its Wine Spectator credential. Prices run steep — this is Jackson Hole, after all — but if you're after serious Italian wine with your house-made pasta, this is your spot.
Old World Focus
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Jackson · Jackson · American
The Silver Dollar Grill isn't going to blow any wine nerds away, but it's a dependable, well-maintained list that respects its audience and earns its Award of Excellence. If you're in Jackson and ordering a serious piece of Wyoming beef, you'll drink well here — just come in with a budget and skip the Caymus.
Solid Range
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Hartland · Hartland · Steak House
Palmer's is a reliable steakhouse wine list that delivers exactly what its suburban clientele wants — well-known California names, solid execution, and nothing too weird. If you're a wine adventurer, you'll want to temper expectations; if you're celebrating with a ribeye and a Jordan Cab, you'll leave satisfied.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Downtown Milwaukee · Milwaukee · Steak House
Ward's House of Prime is exactly what it says it is: a classic Milwaukee steakhouse with a wine list built to match big cuts of beef. The Wine Spectator Award of Excellence is well-earned, but don't come looking for adventure — come looking for a great California Cab and a slab of prime rib.
Plays It Safe
Steep
Basic Stemmed
Willing but Green
Set & Forget
Proper
Milwaukee · Milwaukee · Steak House
Five O'Clock is a reliable, old-school institution that does exactly what it promises — big steaks, big Cabs, zero fuss — and the Wine Spectator nod confirms the list is more than an afterthought. Just don't come here looking for discovery; come here looking for a great bottle of California Cabernet with a perfect ribeye, and you'll leave happy.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
One wine list review, one adventure pick, one quick tip, and a personal note. Every week. Under 500 words.