Maryland’s wild oyster season is back—here’s where to eat, drink and celebrate on the Bay

It’s official: Maryland’s wild oyster season has begun. The season started on Oct. 1 and runs through March 31. This is the legal window when licensed watermen harvest oysters directly from the Chesapeake Bay. While farm-raised oysters grown on aquaculture leases are available year-round, the tradition of eating oysters in fall and winter connects diners to the pride of Bay culture.

Oysters are considered a keystone species in their ecosystem because they play a central role in the ecosystem. Each adult oyster can filter up to 50 gallons of water a day, which helps remove algae and particles that cloud the Bay. Cleaner water helps grasses grow, and that provides habitat for fish, crabs and other marine life.

Historically overharvested, Maryland’s oyster population today shows impressive signs of recovery. A May report from the Maryland Department of Natural Resources (DNR) said overall abundance has risen considerably since 2018, and Maryland’s 2025 stock assessment estimated more than 12 billion oysters in state waters, including 7.6 billion adults (the previous assessment in 2018 counted about 4.5 billion). That is an increase of about 7.5 billion oysters—almost equal to one oyster for every person on Earth, just in the Bay.

For tourists, that means you can have the tasty chance to participate in the comeback story, simply by eating these famously nutrient-dense bivalves. If you’re planning a trip, here are the best ways to enjoy oyster season in Maryland, one half-shell at a time.

Enjoy curated dining and wine pairings on the water

In D.C. and Annapolis, two small businesses turn the Chesapeake Bay into a dining room: Sea Table, founded by chef-sommelier Troy Knapp, takes private groups of roughly six or fewer onto sleek yachts for five-course meals with wine pairings. The menus are up for customization, but Knapp’s classic five-course menu combines gourmet spreads of cheeses, cured meats and fresh seafood. During my voyage, I savored citrus-soaked watermelon and the most well-curated charcuterie board I’ve ever seen, with over 20 selections of layered meats, pickles and dried fruits. Knapp’s wine instinct leans toward the Old World—he favors cool-climate bottles, which he says bring out the brightness in seafood.

Meanwhile, sister company Nautiste, founded by captain Hannah Puckett, hosts private groups up to 12 on restored vintage yachts. The two work collaboratively across both businesses. Puckett has trained with the Oyster Master Guild and brings the passion of a sommelier to oysters. She teaches guests about “merroir”—the idea that oysters, like wine, take on different flavors depending on where they grow. On her voyages, she describes how oysters from the infinite creeks, rivers and tributaries formed by the Chesapeake’s 11,000 miles of shoreline result in variations of brininess and texture. She then turns to Knapp, certified sommelier, for the beverage pairing. His wine list draws heavily from small producers in France, with bottles chosen for freshness, minerality and balance. He likes selections that he says feel alive on the palate and pours wines that keep guests reaching for another oyster or another bite.

Both companies run year-round, and while reservations in high-season months sell out weeks in advance, you can still reserve a private Sea Table experience in October. These small-group trips are perfect for engagements, milestone anniversaries, birthdays or client dinners—and even better when timed with sunset, when the Bay is at its most beautiful.

Attend the annual Baltimore Fishbowl Oyster Shellebration

In the fall, Baltimore’s new favorite newspaper plays host to an event that feels like a love letter to the Bay’s bivalves. The Oyster Shellebration brings together local oyster farms, chefs and winemakers for an evening of slurping, sipping and conversation. Guests can work their way along raw bars piled high with Maryland oysters, then sample prepared dishes that show how versatile shellfish can be. Wines and beers flow freely, selected to highlight the oysters’ salty-sweet flavors. The atmosphere is lively but intimate: it’s part food festival and part neighborhood party. Tickets usually sell out. This year’s edition takes place at True Chesapeake Oyster Co., a restaurant that sprang from an oyster farm and is located in the renovated Whitehall Mill complex in Baltimore.

Follow the Talbot County Oyster Trail

On Maryland’s Eastern Shore, Talbot County—home to harbor towns like Easton, Oxford, St. Michaels and Tilghman Island—has built a literal trail for oyster lovers. The Talbot County Oyster Trail is a mapped route connecting restaurants, raw bars and markets where you can taste the Bay’s signature shellfish in every form: raw, roasted, fried, stewed or tucked into savory pies.

Each stop tells a different part of the Chesapeake story. In St. Michaels, a maritime museum town with cobblestone streets, you might find oysters served beside craft beer. In Oxford, a ferry town dating to the 1600s, oysters appear in stews that taste like tradition. Along Tilghman Island, a working watermen’s village, they arrive on bread as a fried oyster po’ boy, or as simple fried baskets pulled straight from the Bay.

To go, pick up the map from Talbot County Tourism and plan your own route. The Trail runs year-round, but wild oyster season from October to March makes fall and winter an especially abundant time to go.

Slurp oysters and try Baltimore’s classic coddies in Hampden

In Baltimore’s Hampden neighborhood, a former mill district now known for indie shops, rowhouse charm and the annual quirky “HonFest” street fair, Dylan’s Oyster Cellar is my personal favorite go-to for Chesapeake oysters and local seafood. The restaurant started as a pop-up in 2014 and became a permanent spot on Chestnut Avenue, where it now anchors the block with a bustling raw bar. Expect oysters from across Maryland, Virginia and Rhode Island (and—we’ll allow it—some west coast oysters, too), alongside seasonal plates like blue catfish sandwiches, soft-crab sandwiches and coddies—a uniquely Baltimore snack of salt cod and mashed potatoes, a kosher take on the traditional crab cake.

Dylan’s is open for dinner daily. Sit at the counter to watch shuckers at work, or grab a table if you want more room for cocktails and small plates. On my last visit, right before oyster season began, the owner even let me shuck my first oyster as a birthday treat.

Drink Brine, a new Maryland wine made for oysters

Maryland’s Old Westminster Winery, a family-run vineyard in Carroll County, has launched something new this fall: Brine, a crisp white blend styled after Portugal’s vinho verde. Light, fresh and mineral-driven, Brine was designed to pair with Chesapeake Bay oysters and is arriving just in time for wild oyster season.

Ordering Brine supports a worthy cause: For every $28 bottle sold, $1 goes to the Oyster Recovery Partnership, a Maryland nonprofit that plants billions of baby oysters each year on sanctuary reefs and is behind landmark projects like the recently finished Manokin River project on the Eastern Shore.

To celebrate, Old Westminster is teaming up with True Chesapeake Oyster Co. (noticing a pattern here?) for a launch party on Thursday, Oct. 9.

Sip cocktails like a sailor (and try the inventive toasts)

Sailor Oyster Bar is a local hangout spot with serious atmosphere in downtown Annapolis. The bar glows with mood lighting and candles scented like copal, a Mesoamerican tree resin that somehow put me in the mood for seafood. That’s good, because there’s Siberian sturgeon caviar and small plates on the menu, along with snacks like olives and pickles. Cocktails lean adventurous—the menu boasts a rum drink called the “skull puncher” and another with illegal mezcal called “guilty as charged”—but I got a classic negroni before my eye wandered to the inventive toasts. The “bloney” sandwich stacks ribbons of mortadella with aged gouda, greens and spicy mayo, but I opted for the boquerón toast topped with aged anchovy, honey butter, dark chocolate and Fresno peppers. It tasted unexpectedly like Parmesan or pizza. I got the sense Sailor Oyster Bar—or S.O.B. if you’re one of the cool kids—is the kind of spot locals choose for a date or late-night snack with a friend. And then, of course, there’s oysters: order them by the dozen, add a shrimp cocktail, or go full tilt with caviar and bubbles. To drink, you can even gulp down an Oyster Beer Kölsch brewed locally, made just for long nights and salty bites.

Pull up a dockside table in Eastport

For a glimpse of Bay life at its most direct, head to Wild Country Seafood, a family-run dockside in Eastport, the maritime neighborhood across Spa Creek from downtown Annapolis. The neighborhood still feels tied to its watermen roots, and that spirit is alive at Wild Country Seafood, a family-run dockside market owned by longtime waterman Pat Mahoney and his family. They sell what they catch straight from their boats and keep coolers inside stocked with catfish, rockfish and real crab meat.

Outside, picnic tables in a gravel lot invite you to settle in with trays of oysters, crabs and fried seafood. I grabbed a seat near a couple visiting from New Zealand who were working through a dozen oysters together. We exchanged the kind of cross-table conversation that makes the place memorable.

Bring your appetite: Maryland’s oyster season is on

Whether you like them raw, roasted or tucked into a po’ boy, this fall, the Chesapeake’s favorite little gems are best enjoyed (and slurped!) one shell at a time.

The author’s passion for every trip she writes about is sincere. Some experiences may be hosted, but hosting organizations have no control over articles before they’re published.