Wineries and Breweries

From off-centered ales in Milton to estate-grown reds on the Virginia shore — a tasting trail across the peninsula, planned so everyone gets home safely.

Delmarva has always been a place that grows things. Lately, some of what it grows goes into a bottle. Over the past three decades the peninsula has built a real craft beverage scene — breweries, wineries, and brewpubs spread from northern Delaware down through Maryland's Eastern Shore to the tip of Virginia. You don't have to be a connoisseur to enjoy it. A flight of beers at a picnic table, a glass of wine in a vineyard — this is one of the easiest day trips on the peninsula, and it's close no matter where you live here.

This guide starts with the four anchors — the names everybody knows — then maps the wider scene by area. Hours, tour schedules, and tasting fees change with the seasons, so check before you go.

The Delaware Anchors

Dogfish Head Craft Brewery — Milton. The big one, and the reason Delaware is on the national craft-beer map. Dogfish Head started in Rehoboth Beach in the mid-1990s and grew into one of the country's best-known independent breweries, now brewing in Milton with a tasting room and kitchen on site. If you've never been, start here: the Milton campus has the full tour experience, the off-centered lineup you've seen in stores, and plenty of small-batch and experimental pours you can only get at the source. Tours and tasting-room hours run on a seasonal schedule, and weekends draw a crowd, so go early or go on a weekday if you can. Food is available on site, which makes this a legitimate lunch stop, not just a tasting stop.

Four-glass flight on a barrel by a window (white to rose to red).

Nassau Valley Vineyards — Lewes. Delaware's first winery, planted in the early 1990s on farmland just inland from Lewes. This is where Delaware wine started — and the vineyard setting is half the experience, rows of vines a few miles from the bay. Tastings walk you through the estate-grown lineup, and the winery hosts seasonal events through the year. Tasting hours, fees, and event schedules — check before you go. Pair it with a Lewes day: beach or the historic district in the morning, the vineyard in the afternoon.

The Eastern Shore Anchors

Burley Oak — Berlin. The Berlin brewery that put Maryland's Eastern Shore on the craft map — a farm brewery with a taproom on Main Street in one of the peninsula's prettiest small towns. The beer list leans local and rotates often; the vibe is pure small-town hangout, and Berlin itself is worth the drive even if you're not a beer person — the walkable downtown, the shops, the food. Taproom hours and what's on tap — check before you go, since rotating lists mean the menu you saw online last month isn't the one waiting for you.

Chatham Vineyards — Virginia's Eastern Shore. At the far end of the peninsula, an estate winery on a historic farm property, growing vinifera grapes in the sandy soils of the Shore. The tasting room sits in farm country, and the experience here is quieter and more pastoral than the Delaware anchors — a genuine wine-country afternoon at the tip of Delmarva. Hours, tasting fees, and any tour offerings — check before you go.

The Wider Scene, Area by Area

The four anchors are the start, not the list. The peninsula's brewery and winery count keeps growing, and new taprooms open every year. Here, by area, is the shape of what's out there.

Sussex County, beyond Milton and Lewes. Southern Delaware has the densest brewery cluster on the peninsula, and the drives between stops are short. Lewes alone has Big Oyster Brewery, with a large taproom, and a Crooked Hammock location built around an outdoor backyard and a kitchen; Crooked Hammock also operates in Middletown. Georgetown has 16 Mile Brewery. On the wine side, Salted Vines Vineyard & Winery pours estate wines at its family-owned vineyard in Frankford, inland from the beaches. Up in Kent County, Harvest Ridge Winery sits on the Mason-Dixon line in Marydel, with a tasting room open daily, and Pizzadili Vineyard & Winery pours in a Tuscan-style vineyard setting in Felton.

Beach-town brewpubs. Rehoboth, Dewey, Bethany, Fenwick, and Ocean City each have their own brewery or brewpub scene — many of them within walking distance of the boardwalk or the beach, which makes them summer-evening naturals. These tend to be food-first operations: real kitchens, full menus, beer brewed steps from your table.

Rehoboth and Dewey: Rehoboth is home to Dogfish Head Brewings & Eats — the original Dogfish Head brewpub — along with Revelation Craft Brewing and Thompson Island Brewing; Dewey Beach has Dewey Beer Co. All sit within walking distance of the beach, which makes them natural dinner-and-a-flight stops.
Bethany and Fenwick: smaller, quieter brewpub and taproom options on the quieter end of the coast.
Ocean City: brewpubs on the bay side and in midtown, built for groups and game days.

Maryland's Eastern Shore. The Shore's beverage scene stretches from the upper counties down through St. Michaels, Easton, Cambridge, and Salisbury — breweries, a handful of wineries, and farm-based operations that fit the agricultural character of the region. Distances are longer here, so plan one stop per town rather than a marathon.

Tasting-room counter scene with flight + flowers.

Breweries: farm taprooms and small-town Main Street breweries scattered from the upper Shore down to Salisbury — plan one town per outing.
Wineries: the mid-Shore pours from Kent Island down to Berlin. Windmill Creek Vineyard & Winery in Berlin pairs estate wines with a farm-kitchen restaurant. Bordeleau Vineyards & Winery grows its grapes in Eden, on Wicomico Creek, and also pours at a tasting room on South Talbot Street in St. Michaels. Layton's Chance Vineyard & Winery is a family farm winery in Vienna, with picnic grounds and a summer concert series. Far Eastern Shore Winery pours in Easton, including dessert and spiced wines. On Kent Island, Cascia Vineyards and Love Point Vineyards & Winery are small waterfront and artisan wineries pouring on weekend schedules. Up the Shore, Crow Vineyard & Winery pours dry estate wines on a third-generation farm in Kennedyville, Broken Spoke Vineyard & Winery pours in Earleville, and Bohemia Manor Farm in Chesapeake City is home to Chateau Bu-De Winery, with Blue Elk Vineyard pouring nearby in North East.

Virginia's Eastern Shore. Smaller and quieter, like everything down here — a couple of wineries and the odd brewery, spread across farm towns between the bay and the seaside. Worth building into a Chincoteague or Onancock weekend rather than a standalone trip.

Wineries: beyond the Chatham anchor, Bloxom Vineyard & Winery grows Bordeaux varieties on a 35-acre farm in Bloxom and pours by reservation, with a small bistro on site.
Breweries: a handful of small breweries in the Shore's farm towns — call ahead; hours are limited.

Making a Day of It

Tastings and tours. At breweries, order a flight — four to six small pours — instead of committing to a pint of something untested. At wineries, the standard tasting pours through five or six wines; ask questions, because the people pouring usually love talking about the vineyard. Brewery tours are worth taking once at each anchor — you see the equipment, you learn the process, and the samples at the end taste better for it. Tour times are limited and some require reservations — check before you go.

Beer flight — five mini mugs, amber to stout, on a wooden paddle.

Eat along the way. Don't taste on an empty stomach — this is the entire food-pairing section in one sentence. The anchors with kitchens make it easy. For the rest, build lunch into the route: a brewery next to a good restaurant is a feature, not a coincidence. Salty, fatty foods are your friend with beer and wine both.

The driver question. Plan this before the first pour, not after the third. Options that work on Delmarva: a designated driver (the breweries all have good non-alcoholic options now), a rideshare for a single-town outing, or one of the seasonal trolley or shuttle services that run in the beach towns in summer (routes and schedules). Multi-stop rural routes are the hardest to cover, so keep those to two stops with a long lunch between them.

When to go. Fall is the sweet spot — harvest energy at the wineries, Oktoberfest-adjacent releases at the breweries, smaller crowds than summer, and the drives are prettier. Summer works for the beach-town brewpubs but expect waits. Winter is the insider's season: taprooms are quiet, the staff has time to talk, and you'll often find experimental small batches that never make it to distribution. Holiday events at the wineries make a good December outing — check their schedules before you go; see the Holiday Issue for the season's full calendar.

Figures and availability are general information. Hours, tour schedules, tasting fees, and seasonal offerings change with the seasons — check current details before you go.