Kentucky's Best Wine List Lives in a 1938 Landmark
Chevy Chase · Lexington · Upscale American · Visit Website ↗
Reviewed June 4, 2026
Wingman Metrics
Walking into Coles 735 Main, the wine list signals that someone here actually cares — this isn't a steakhouse afterthought with a Caymus and a prayer. The list runs 80 to 130 bottles deep, holds a Wine Spectator Restaurant Award, and covers enough ground to reward both the Napa loyalist and the person quietly hoping to find an Oregon Pinot on a Kentucky Main Street. The room — a restored 1938 building — matches the ambition.
California dominates, as you'd expect from a steak-forward menu, with serious representation from Napa Valley (Stag's Leap, Duckhorn, Cakebread, Caymus, Turley) and Sonoma (Belle Glos). What's more interesting is the Pacific Northwest showing — Penner-Ash out of Oregon and the Underground Wine Project's 'Idle Hands' from Red Mountain, Washington bring genuine depth to the list. France and Italy are present but supporting cast, with Bordeaux and Burgundy filling the high-end slots and Tuscany and Piedmont covering the red-meat-friendly middle tier. The gaps are in the Southern Hemisphere, where Argentina and Chile appear to exist mainly as price anchors rather than thoughtful selections.
Fourteen pours by the glass is a legitimate program, ranging from around $12 to $23 — solid spread for a mid-market fine dining room. We'd want to know more about how frequently those selections rotate, and with no active specials program to speak of, the glass list feels like it could use a shot of energy. That said, having 14 options in Lexington, Kentucky puts Coles comfortably ahead of most competition in the market.
Underground Wine Project 'Idle Hands' Red Mountain, Washington 2015 — Not publicly listed
Red Mountain Washingon reds consistently punch above their weight class, and the Underground Wine Project is a producer worth knowing. In a list weighted toward Napa, this is the bottle that actually has something to say — and likely priced below the Napa heavyweights while delivering comparable structure and intensity.
Penner-Ash Wine Cellars Pinot Noir, Oregon
Penner-Ash is a Willamette Valley producer that serious Oregon Pinot drinkers know well, but it tends to get overlooked on lists dominated by California names. In a room full of people ordering the Stag's Leap, this is the bottle that rewards curiosity — more nuance, more complexity, and a story worth telling at the table.
Cakebread Cellars Chardonnay 2018
At $95 on the list against a $45 retail price, this is a 111% markup on a wine that's already everywhere. Cakebread Chardonnay is fine — it's also on every hotel restaurant list in America. The markup here is the real problem: you're paying a heavy premium for a label, not a discovery.
Stag's Leap Wine Cellars 'Artemis' Cabernet Sauvignon 2018 + Filet Mignon
Artemis is the approachable entry point into the Stag's Leap portfolio — structured enough to hold up to a prime filet, polished enough not to overpower it. At $165 on the list it's not cheap, but at roughly 74% over retail it's also the most fairly priced of the Napa heavyweights on this list. This is the move if you're celebrating.
✔️ The Bottom Line
Coles 735 Main is doing real work on a wine list in a market that doesn't always demand it — a sommelier on staff, proper glassware, and genuine depth beyond the Napa greatest hits make it the best wine destination in Lexington by a comfortable margin. The markups are steep in spots and there's no specials program to speak of, but for a date night or a special occasion dinner in Kentucky, this is the room.
South Lexington / Harrodsburg Road · Lexington · Italian, Contemporary Italian, Seafood
Giuseppe's isn't a wine destination, but Monday night half-price bottles make it one of the better value plays in Lexington — show up then, lean on the seafood, and you'll leave happy. Any other night, the markups ask a lot and the list doesn't ask you to think very hard.
Solid Range
Steep
Basic Stemmed
Willing but Green
Occasional
Acceptable
Lansdowne / Nicholasville Road · Lexington · Italian-American
Sutton's isn't a wine destination, but it's a perfectly reasonable place to drink a bottle of Chianti while someone else handles the cooking. The Tignanello alone earns this list a second look if you know to ask for it.
Plays It Safe
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Downtown / Gratz Park · Lexington · New American / Southern
Jonathan at Gratz Park is the kind of reliable wine room you'd expect from a historic inn with a real sommelier — competent, well-stocked, and leaning safe. Pricing is on the steeper side and the list won't surprise you, but in Lexington, this is still one of the better places to order a full bottle with dinner.
Solid Range
Steep
Basic Stemmed
Knowledgeable & Friendly
Set & Forget
Proper
Palomar / Harrodsburg Road · Lexington · Italian, Seasonal American-Influenced
Bella Notte isn't a wine destination, but it's a reliable neighborhood spot with one genuinely smart move: Thursday half-price bottles turn a steep list into a real value play. Go on a Thursday, order the Decoy Cab with a wood-grilled steak, and you'll leave happy.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Active Program
Acceptable
Downtown · Lexington · Italian
ItalX is a dependable Italian wine list for a night out downtown — not exciting, but not embarrassing either. Send a friend here knowing they'll drink well enough, as long as they steer toward the Italian reds and away from the obvious tourist traps.
Solid Range
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Summit at Fritz Farm · Lexington · New American / Southern
33 Staves is a perfectly competent hotel wine list in a city where nobody's really coming for the wine. Drink it for what it is, keep your expectations calibrated, and save the serious bottle hunting for somewhere else.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
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
Belmont Shore · Long Beach · Upscale American
Nick's on 2nd is a dependable neighborhood wine stop — solid list, familiar producers, nothing that'll blow your mind but nothing that'll disappoint a table of mixed drinkers. Send a friend here for a date night, just tell them to order the Duckhorn and leave the Jordan for someone else.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Downtown Jackson · Jackson Hole · Upscale American
The Blue Lion is a reliable wine program in a genuinely lovely setting — live guitar, historic house, serious game on the menu. The markup on some bottles is hard to forgive, but if you order with intention there are real wines here worth drinking. Send your friends, just brief them on what to avoid.
Solid Range
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
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