The Red Lion Inn
Historic Charm Meets a Dependable Pour
Stockbridge · Stockbridge · American · Visit Website ↗
Reviewed April 16, 2026
Wingman Metrics
First Impression
Walking into The Red Lion Inn — a place that's been around since 1773 — you half expect the wine list to be as frozen in time as the wallpaper. It's not. The list is tighter and more focused than the sprawling dining room might suggest, leaning into California, France, and Italy with enough conviction to earn its Wine Spectator Award of Excellence. It reads like someone actually made choices here, which counts for a lot in a Berkshires inn.
Selection Deep Dive
The 150-plus bottle list is anchored by California heavyweights and French classics — Caymus, Jordan, and Stag's Leap carry the Napa banner while Louis Jadot and Joseph Drouhin handle Burgundy duty reliably if not thrillingly. Italy gets a serious nod with Antinori's Tignanello on the list, which signals real ambition. The gaps are mostly in the Southern Hemisphere and anything remotely natural or obscure, but this is a historic New England inn, not a Brooklyn wine bar — the focus suits the room. John Reilly on staff as sommelier gives the list a credibility anchor that most country inns can't claim.
By the Glass
With 12 to 20 options by the glass, there's enough range to navigate a table with divided loyalties — a Chardonnay drinker and a Cab person won't have to negotiate. The Chateau Ste. Michelle Riesling showing up in the glass pour rotation is a smart crowd-pleaser that also happens to be genuinely good. We'd like to see more rotation and adventurous pours, but the program is functional and staffed well enough that you can ask questions and get real answers.
Chateau Ste. Michelle Riesling — $40
One of Washington State's most consistent producers at a price point that doesn't require a second mortgage. Off-dry, food-friendly, and criminally underordered by the Cab crowd — grab it with the lobster bisque.
Antinori Tignanello
Most people at an inn like this are defaulting to a Napa Cab without looking further. Tignanello — a Sangiovese-Cabernet blend from one of Tuscany's greatest estates — is sitting right there and will out-charm anything in the California section at a comparable price. It's the move.
Caymus Vineyards Cabernet Sauvignon
Caymus is fine wine, no argument — but it's also the most marked-up recognizable label on any American restaurant list. You're paying for the name recognition here, and in that price range, the Jordan or Stag's Leap will deliver more interesting drinking for less ego.
Jordan Vineyard & Winery Cabernet Sauvignon + Roast Prime Rib of Beef
Jordan's Cab is built for exactly this moment — classic, structured, not overextracted, with just enough fruit to stand up to a proper prime rib without fighting it. This is the kind of pairing that makes a cold Berkshires night feel like a very good decision.
✔️ The Bottom Line
The Red Lion Inn's wine list won't blow your mind, but it's honest, well-kept, and staffed by someone who actually knows what's on it — a genuinely rare thing for a destination inn. If you're making the trek to Stockbridge, this is a safe and often rewarding place to drink.
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