Solid steakhouse list, one eyebrow-raising markup
Downtown · Winston Salem · Upscale American Steak and Seafood · Visit Website ↗
Reviewed June 25, 2026
Wingman Metrics
The Downtown Grille looks the part — polished room, white tablecloths, the kind of place where you expect a serious wine list to match the $45 ribeye. What you actually get is a respectable but predictable selection that leans hard into crowd-pleasing California names and doesn't stray far from the mainstream. It's fine. It's just not adventurous.
The list skews American with a California center of gravity — Silver Oak showing up as a featured bottle at curated dinners tells you exactly where the restaurant's head is at. There's a nod to Argentina via Zuccardi Malbec, and the occasional wine dinner spotlights North Carolina's own Biltmore, which is a nice local touch even if Biltmore rarely makes wine enthusiasts lose their minds. Expect recognizable labels that sell themselves, not a list designed to make you discover something new. The regional gaps are real — no meaningful European depth is apparent, and if you came hoping for Burgundy or Barolo, lower your expectations now.
Glass pours start at $10 during promotional pricing, which gives you an accessible entry point in an otherwise upscale setting. The full by-the-glass program details aren't published prominently, which usually means the rotation is modest and the list doesn't change much. What's there gets the job done for a steakhouse night out, but don't expect anything that'll make you put down your phone and pay attention.
Zuccardi Malbec — Unknown — confirm on-site
Zuccardi is one of Argentina's most respected Malbec producers, making wine in Mendoza's Valle de Uco at altitude. If this is priced reasonably, it's the most food-serious bottle on a list otherwise full of safe choices — and it'll hold its own against any red meat on the menu.
Biltmore Estate Wine
Most people order this as a novelty and promptly forget about it, but featuring a North Carolina wine at a wine dinner shows the kitchen takes it seriously. Biltmore's reds have improved considerably in recent years — if they're pouring one of the estate's Cabernet-based bottles, it's worth a try for the story and the surprise.
Provençal Dry Rosé
A 167% markup on a $15 retail rosé — landing at $40 on the menu — is aggressive for a wine that doesn't require a special occasion or a cellar. There are plenty of rosés at this price point in any wine shop, and you're not getting anything rare or allocations-only here. Order something else.
Zuccardi Malbec + Prime Steak
High-altitude Malbec brings dark fruit, firm tannins, and enough acidity to cut through the fat on a prime cut. Zuccardi in particular runs more structured and serious than your average Malbec — it's built for red meat and earns its place next to whatever the kitchen is putting on the grill.
✔️ The Bottom Line
The Downtown Grille is a reliable upscale night out in Winston-Salem with a wine list that matches the room — safe, polished, and built for people who already know what they like. Watch the rosé markup, lean into the Zuccardi, and you'll leave happy.
Reynolda / North Winston-Salem · Winston Salem · Upscale American
Graylyn Estate is a genuinely beautiful place to have dinner, but the wine list is an afterthought in a room that deserves intention. Order the sea bass, grab the La Crema, and try not to think too hard about what this list could have been.
Grocery Store
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Clemmons · Winston Salem · New American
Sixty Vines is a solid, reliable wine stop in Winston-Salem — the by-the-glass breadth is real and the staff knows their stuff, but the list reads like a greatest hits album rather than anything adventurous. Come for the volume, stay for the pizza, but don't expect to have your mind changed about wine.
Crowd Pleasers
Steep
Basic Stemmed
Knowledgeable & Friendly
Set & Forget
Proper
Downtown · Winston Salem · Indian
Oh' Calcutta's wine list is unremarkable on its own — but Tuesday nights flip the script entirely, and a $19 Pinot Noir with lamb vindaloo is a genuinely good time. Come for the food, plan around Tuesday, and don't overthink it.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Active Program
Acceptable
Downtown · Winston Salem · American
Cin Cin isn't a wine destination, and it doesn't pretend to be — but Wednesday half-price wine all day on bottles and glasses turns a generic list into a genuinely good deal with a burger in hand. Show up any other night of the week and order a beer.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Seasonal Rotation
Acceptable
Brookstown · Winston Salem · Italian
Quanto Basta punches above its weight for a mid-size Southern city Italian spot — the Italian-focused list is thoughtful, the prices are fair, and Thursday half-price bottles make it one of the best weekly wine deals in Winston-Salem. Come hungry, come on a Thursday, and order the Falanghina.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Seasonal Rotation
Acceptable
Silas Creek Pkwy · Winston Salem · Japanese / Sushi
Umi is a fun hibachi night out, and the wine pricing is honestly fairer than it has any right to be — but the list itself is an afterthought, and no amount of fair markup fixes a selection that's two bottles deep in personality. Order sake, or a cocktail, and come back to us when they add a Grüner Veltliner.
Grocery Store
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
One wine list review, one adventure pick, one quick tip, and a personal note. Every week. Under 500 words.