Winston Salem

Divine Llama Vineyards Tasting Room & Bistro

· Winston Salem · Winery Tasting Room / Light Bites

The Wild Card

Divine Llama is a fun, farm-genuine detour if you're exploring North Carolina wine country and want something local and unpretentious. Don't come for depth or discovery beyond the estate — come for the story, the setting, and a glass of Traminette you probably wouldn't have ordered anywhere else.

West End Cafe

· Winston Salem · American Cafe

The Reliable

West End Cafe isn't a wine destination, but it's a perfectly decent place to drink something decent without overpaying for it. Send a friend here if they want wine with dinner and aren't looking to make an event out of it.

Little Pep

· Winston Salem · Wine Bar / Market

The Wild Card

Little Pep is doing something genuinely uncommon for Winston-Salem: a short, confident, all-by-the-glass natural wine list with real producer cred and fair prices. Send a curious friend here; skip sending someone who wants a Napa Cab.

Manolo's Boutique Wines

· Winston Salem · Wine Bar / Small Plates

The Wild Card

Manolo's is a genuine surprise for Winston-Salem — a focused, serious wine program that gives you by-the-glass access to bottles most restaurants lock behind full-bottle commitments. The markup is not subtle, but you're paying for curation and access, and if you pick smart, the experience delivers.

Medaloni Cellars

· Winston Salem · Winery Restaurant / Small Plates

The Wild Card

Medaloni Cellars is doing something genuinely interesting in Winston-Salem: building a single-producer list that doesn't bore you into ordering a cocktail. If you have any curiosity about what North Carolina wine can actually do, this is the place to test it.

Carolina's Vineyards & Hops

· Winston Salem · Wine Bar / Taproom

The Lazy List

Four house wines does not a wine bar make. Unless you're here for the hops side of things, the wine program at Carolina's Vineyards & Hops isn't worth centering your evening around — order a beer and call it a night.

End Posts Restaurant at JOLO Winery & Vineyards

· Winston Salem · Winery Restaurant / American

The Wild Card

End Posts is a single-producer list by design, and if you're good with that — and in the mood to dig into what one North Carolina winery can actually do — it delivers a genuinely fun afternoon. Don't come expecting a broad cellar; do come expecting to leave with a new favorite local label.

Cugino Forno Pizzeria

· Winston Salem · Neapolitan Pizza

The Lazy List

Cugino Forno isn't trying to be a wine destination, and the five-bottle list makes that abundantly clear. The prices are fair enough that you won't feel ripped off, but if wine matters to you on a night out, this is a BYOB situation — check their corkage policy.

River Birch Lodge

· Winston Salem · Lodge-style American / Seafood & Grill

The Lazy List

River Birch Lodge's wine list isn't a wine list — it's a mimosa station with a port chaser. Order a cocktail with dinner and save the Tawny for the end.

Graylyn Estate Dining

Reynolda / North Winston-Salem · Winston Salem · Upscale American

The Lazy List

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.

Sixty Vines

Clemmons · Winston Salem · New American

The Reliable

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.

Oh' Calcutta

Downtown · Winston Salem · Indian

The Wild Card

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.

Cin Cin Burger Bar

Downtown · Winston Salem · American

The Wild Card

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.

Quanto Basta Italian Eatery & Wine Bar

Brookstown · Winston Salem · Italian

The Wild Card

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.

Umi Japanese Steakhouse & Sushi

Silas Creek Pkwy · Winston Salem · Japanese / Sushi

The Lazy List

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.

Village Tavern Reynolda

Reynolda Village · Winston Salem · American

The Reliable

Village Tavern Reynolda isn't a destination wine list, but it earns its keep with real range, at least one smart Italian pick, and a Wednesday half-price program that makes it genuinely worth planning around. Send a friend here on a Wednesday — tell them to order the Arneis.

Firebirds Wood Fired Grill

Hanes Mall / Strickland Rd · Winston Salem · American Steakhouse

The Reliable

Firebirds isn't trying to reinvent anything, and the wine list reflects that — it's a dependable, California-forward selection that does its job without embarrassing itself. If you want adventure, look elsewhere; if you want a solid bottle with a good steak in a comfortable room, this gets you there.

The Katharine Brasserie & Bar

Downtown · Winston Salem · French Brasserie, European, New American

The Reliable

The Katharine is a genuinely good wine destination by Winston-Salem standards, with a Champagne list that punches above its weight class for a mid-sized Southern city. Just go in knowing you're paying hotel-rate markups — budget accordingly and lean toward the grower Champagnes and local bottles for the best return.

Bleu Restaurant and Bar

Robinhood / North Winston · Winston Salem · Modern American, Southern

The Reliable

Bleu is a reliable wine destination for Winston-Salem — not a destination list, but a thoughtful one with genuine highlights buried among the familiar. The markups sting a little, but the presence of Puligny-Montrachet and Tavel rosé on a neighborhood restaurant list tells you someone here actually gives a damn.

The Downtown Grille

Downtown · Winston Salem · Upscale American Steak and Seafood

The Reliable

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.

Sir Winston Wine Loft & Restaurant

Downtown · Winston Salem · Contemporary American

The Reliable

Sir Winston is the rare hotel restaurant that makes a real effort on wine, and for Winston-Salem, that counts for a lot. Pricing runs steep enough that you'll feel it by the second bottle, but the selection earns at least one visit from anyone who takes wine seriously.

Jeffrey Adams on Fourth

Downtown · Winston Salem · Contemporary American Steakhouse and Grill

The Reliable

Jeffrey Adams on Fourth isn't a wine destination, but it's a decent place to drink familiar wines with a great steak — and on Tuesday, that half-price deal makes the whole thing a lot easier to love. Come for the ribeye, drink the Stags Leap, and don't overthink it.

Cibo Trattoria

Downtown · Winston Salem · Italian

The Reliable

Cibo Trattoria isn't going to blow a wine geek's mind, but it's doing more than most Italian spots in Winston-Salem bother to do — and if you order smart, you'll drink well. Stick to the Italian side of the list and you'll leave happy.

Ryan's Restaurant

Winston-Salem · Winston Salem · American Steakhouse

The Reliable

Ryan's isn't trying to surprise you, and it doesn't — but two decades of Wine Spectator recognition don't happen by accident, and a well-maintained California list in a proper steakhouse setting earns its keep. Send a friend who wants a great Napa Cab with a great cut of beef; don't send one who's hunting for discovery.

Katharine Brasserie & Bar

Downtown Winston-Salem · Winston Salem · French

The Rager

Katharine Brasserie is the real deal for the Triad — a deep, well-curated list in a setting that actually honors it. The markup can sting and there's no dedicated sommelier to guide you through, but if you know what you're looking for, this list rewards the effort.

Sage & Salt Bistro

Winston Salem · Winston Salem · American

The Rager

Sage & Salt is the real deal — a Wine Spectator Best of Award of Excellence recipient that actually earns it rather than just hanging the plaque. If you're within driving distance of Winston-Salem and you care about what's in your glass, this one belongs on your list.