Best Wine Lists in Maryland

Roma Alla Pala

Downtown Easton · Easton · Roman-style pizza

The Lazy List

Roma Alla Pala is absolutely worth visiting for the pizza — but the wine list is an afterthought with steep markups on recognizable grocery-store bottles. Order the Prosecco, focus on the food, and save the serious wine drinking for another night.

T at the General Store

Royal Oak · Easton · Upscale New American with Global Influences

The Wild Card

T at the General Store is a destination for the food first, and the wine list knows that — it's curated just enough to be useful without trying to steal the spotlight. Come on a Wednesday, order the LAN Crianza, and let the chef do the rest.

Tiger Lily

Downtown Easton · Easton · Fusion (global/Asian-influenced American)

The Reliable

Tiger Lily won't win any awards for its wine program, but it earns its keep — fair prices, a thoughtful short list, and a few genuinely good picks buried in there for anyone willing to look past the Chardonnay. If you're eating here, drink the Eroica.

Scossa Restaurant & Lounge

Downtown Easton · Easton · Authentic Northern Italian

The Reliable

Scossa is a legitimately good restaurant that happens to have a wine list more interested in Napa status symbols than in what's on the plate — but with the Brunello and Barbaresco hiding in there, and a strong by-the-glass count, there's enough to work with if you look past the obvious picks. Send your friends, but brief them first.

Out of the Fire

Downtown Easton · Easton · Contemporary American

The Reliable

Out of the Fire is a dependable wine stop in a town that doesn't have many — the California-focused list is a little one-note, but the pricing is honest and there are a few genuinely interesting bottles hiding in the lineup. Send a friend here for dinner, point them to the Cab Franc, and tell them to skip the bourbon barrel novelty act.

Davis' Pub

Eastport · Annapolis · American pub fare

The Lazy List

Davis' Pub is a great place to drink — just not wine. The list is inoffensive and priced fairly, but it exists as an afterthought in a place where the real action is cold drafts and steamed crabs. Order the Brancott if you must, then pivot to beer.

Chart House

Spa Creek · Annapolis · Seafood / Steak

The Reliable

Chart House Annapolis is a reliable wine list in a genuinely great setting — you'll drink well enough, but you're paying for the view as much as the pour. Go in with eyes open on the markup and lean on the California stalwarts that earned their spots here.

Smashing Grapes

Towne Centre Area · Annapolis · Wine Bar / Mediterranean

The Rager

Smashing Grapes is quietly one of the better wine programs in the mid-Atlantic, operating in a market that doesn't always demand it — which makes it even more impressive. Send a friend here, absolutely, and tell them to skip the safe picks.

Red Red Wine Bar

Upper Main Street · Annapolis · Wine Bar / Bistro

The Wild Card

Red Red Wine Bar is a genuinely fun, accessible spot if you go in knowing what it is: a bubbly-forward wine bar built for socializing and sharing flights, not deep-dive cellar exploration. Send your friend here for a casual night out — just don't send them expecting a sprawling wine list.

Reynolds Tavern (Tea & Wine)

Church Circle · Annapolis · Tavern / Afternoon Tea

The Wild Card

Reynolds Tavern is the kind of Wild Card that earns its badge by being completely sincere — a 275-year-old tavern that stocks Vieux Télégraphe and Maryland Albariño without making a big deal about it. If you're in Annapolis and skipping wine here in favor of a generic hotel bar down the street, that's on you.

Blackwall Hitch

Eastport · Annapolis · Seafood / Raw Bar

The Reliable

Blackwall Hitch isn't a wine destination, but it's a reliable spot to drink something decent without getting gouged — especially during happy hour. Send a friend here if they want a glass on the water, not if they're chasing something to talk about.

Eastport Kitchen

Eastport · Annapolis · American Cafe

The Wild Card

Eastport Kitchen isn't a wine destination, but it's also not pretending to be one — and for a casual neighborhood café in Annapolis, the wine program punches well above its weight class. The markups are mostly reasonable, the by-the-glass selection is genuinely broad, and if you know what to order, you can drink pretty well with your burger.