A Weekend Wine & Oyster Itinerary

Maryland has been making wine seriously since the 1970s, but it is in the last decade that the combination of improved viticulture, climate shifts, and a serious new generation of winemakers has produced wines worth seeking out. The Chesapeake oyster harvest, meanwhile, peaks in October, when the water temperature drops and the oysters fatten into something extraordinary. These two pleasures, combined in a 48-hour itinerary, are among the best things you can do from The Alderton in autumn.

Friday evening: arrive at The Alderton and check into your room. Dinner at The Compass Rose — order the raw bar, ask sommelier Daniel Harrow to open a Maryland Gruner Veltliner from Black Ankle Vineyards, and start with the oysters from the Choptank River. These are the best bivalves in the Chesapeake in October: sweet, cold, saline, and substantial.

Saturday: drive west to the wine country of Carroll and Frederick counties. The three producers worth your Saturday are Boordy Vineyards (Maryland’s oldest, with a serious Cab Franc), Black Ankle Vineyards (the best Gruner in the state), and Portofino Winery in Woodbine (a small, family-run operation making excellent dry rosé). All three have tasting rooms open Saturday from 11 am. Lunch at the Portofino patio if the weather holds.

Saturday evening: return to Annapolis and walk to one of the City Dock oyster bars for a second raw bar session. The October Choptanks and Patuxents are at their peak, and the contrast with the Silver Queen corn oysters from the Eastern Shore is worth tasting side by side. Ask the shucker which are coldest.

Sunday morning: brunch at The Compass Rose. The Crab Benedict and a Bloody Mary made with house-pickled vegetables is the correct conclusion to a weekend built around the Chesapeake’s two finest harvests. Leave no later than 1 pm and you will beat the Sunday traffic on Route 50.