Breweries & Wineries | Chesapeakehomeliving

Breweries, Wineries & Dockside Bars

Breweries, wineries, and dock bars are a defining part of Chesapeake Bay summer traditions, where locals and visitors gather for waterfront beers, coastal cocktails, and relaxed outdoor wine tastings from Maryland to Virginia. From lively dock bars along the Bay’s tributaries to small, no‑fuss Chesapeake wineries pouring regional reds, whites, and sparkling wines, these spots capture the laid‑back, sun‑soaked spirit of Bay life. Whether you’re arriving by boat or by land, the region’s craft breweries, waterside bars, and intimate vineyards offer unbeatable views, fresh air, and the unmistakable feeling that summer has finally arrived.

Visit These Cool Breweries Around the Chesapeake Bay Region

North Bay

Bay Bridge Region

Bog Turtle Brewery, Rising Sun, MD

Hopkins Farm Brewery, Harve de Grace, MD

Firetower Farm Brewery, Colora, MD

Red Brick Station at White Marsh Brewing, White Marsh, MD

Union Craft Brewing, Baltimore, MD

Checkerspot Brewery, Baltimore, MD

Diamondback Brewing Company, Baltimore, MD

DuClaw Brewing Company, Rosedale, MD

Monument City Brewing, Baltimore, MD

Oliver Brewing Co, Baltimore, MD

Peabody Heights Brewery, Baltimore, MD

Ruhlman Brewery, Hampstead, Maryland

Scorpion Brewing Co, Owings, MD

Heavy Seas Beer, Halethorpe, MD

Independent Brewing Co, Bel Air, MD

Jailbreak Brewery, Laurel, MD

B.C. Brewery, Hunt Valley, MD

Black Flag Brewery, Columbia, MD

Guinness Open Gate Brewery, Halethorpe, MD

Hysteria Brewery, Columbia, MD

Key Brewing, Dundalk, MD

Manor Hill Brewery, Ellicott City, MD

Mobtown Brewing, Baltimore, MD

Nepenthe Brewing Company, Baltimore, MD

Crooked Crab Brewing, Odenton, MD

Pooles Island Brewing Company, Middle River, MD

M8, Baltimore, MD

Big Truck Farm Brewery, Parkton, MD

Battery Island Brewing Company, Havre de Grace, MD
Watchtower Brewing Company, Aberdeen, MD

Falling Branch Brewery, Street, MD

Slate Farm Brewery, Whiteford, MD

Eastern Shore Brewing, St. Michaels, MD

Evolution Craft Brewing Company, Salisbury, MD

Bayheads Brewing Company, Chesapeake City, MD

Bull & Goat Brewery, Centreville, MD

Chesepiooc Brewing, Crofton, MD

Cult Classic Brewery, Stevensville, MD

Patriot Acres Farm Brewery, Sudlersville, MD

Forward Brewing, Annapolis, MD

Pherm Brewing, Grambrills, MD

Ten Eyck Brewing Company, Queenstown, MD

Old Barn Brewery, Arnold, MD
Eden Town Brewing, Denton, MD

Riley’s Mill Ale Works, Chestertown, MD
Big Truck Farm Brewery, Queenstown, MD

Southern Maryland

Ruddy Duck Brewery and Grill, Dowell, MD

Ruddy Duck Brewery, Dowell, MD

Jubilee Farm Fermentations, Leonardtown, MD

Patuxent Brewing Company, Waldorf, MD

Virginia Eastern Shore

Virginia – North of BBT

Black Narrows Brewing Company, Chinoteague, VA

Cape Charles Brewing, Cape Charles, VA

Caboose Tavern, Vienna, VA

Ballad Brewing, Danville, VA

Adventure Brewing Company, Stafford, VA

AleWerks Brewing Company, Williamsburg, VA

Center of the Universe Brewing Company, Ashland, VA

St. George Brewing Company, Hampton, VA

Maidstone Meadery, Stevensburg, VA

Brass Cannon Brewing, Williamsburg, VA

Capstan Bar Brewing Company, Hampton, VA

The Vanguard Brewpub and Distllery, Hampton, Virgina

Tradition Brewing Company, Newport News, VA

Colonial Beach Brewing, Colonial Beach, VA.

2 Witches Winery & Brewing Co., Danville, VA

The Virginia Beer Company, Williamsburg, VA,

Alewerks Brewing Company, Williamsburg, VA

That Damn Mary Brewing Company, Hayes, VA

Pleasure House Brewing, Virginia Beach, VA

Smartmouth Brewing Company, Norfolk, VA

Young Veterans Brewery Company, Virginia Beach, VA

Back Bay Brewing Co, Virginia Beach, VA

O'Connor Brewing Co., Norfolk, VA

Pleasure House Brewing Co, Virginia Beach, VA

COVA, Norfolk, VA

Commonwealth Brewing Co, Virginia Beach, VA

Wharf Hill Brewing Company, Smithfield, VA

MoMac Brewing Company, Portsmouth, VA

The Bold Mariner Brewing Company, Norfolk, VA

Rip Rap Brewing, Norfolk, VA

New Realm Brewing, Virginia Beach, VA

Nansemond Brewing Station, Suffolk, VA

Benchtop Brewing Company, Norfolk, VA

Big Ugly Brewing, Chesapeake, VA

Reaver Beach Brewing Company, Virginia Beach, VA

Voodoo Brewing Co., Virginia Beach

Virginia - North of BBT

Wineries Around the Chesapeake Bay Region

Wineries Located in the Virginia, North of BBT

New Kent Winery & Vineyard, New Kent, VA -Opened in 2008 in a century old building. There is spacious outdoor seating with vineyard vistas surrounding the winery and is dog friendly.

Saude Creek Vineyards, Lanexa, VA - Saude Creek Vineyards is very popular and located on the Pamunkey River. Besides the wines, they are known for the barbeque food truck and Mr. Saude, the campus cat. The winery is pet friendly.

Jacey Vineyards, Heathsville, VA- Arrive by boat to Jacey Vineyards which sits on a peaceful 150 acre waterfront property. Aside from wines, Jacey has craft beer and ciders.

Ingleside Vineyards, Oak Grove, VA - One of the largest wineries in Virginia on beautiful grounds. The courtyard and fountain is where people set up to picnic and drink the award winning wines.

Dog and Oyster - The Vineyard, Irvington, VA - The Dog and Oyster is the new vineyard of The Hope and Glory Inn. The unique name for the vineyard was created to honor the rescue dogs that “work” at the vineyard and to honor the Chesapeake Bay oyster.

Gauthier Vineyard, Barhamsville, VA - Gauthier Vineyard is a new family-owned working farm, equestrian center, vineyard and winery in scenic New Kent County. This quaint winery is now home to the Inn at Woodmont Plantation.

General's Ridge Vineyard & Winery, Hague, VA -General's Ridge Vineyard and Winery, named in honor of its retired 2-Star Marine Corps owner, is located on an historic farm between the Potomac and the Rappahannock Rivers. In July they expanded their weekend hours.

Good Luck Cellars, Kilmarnock, VA - Good Luck Cellars is 10 years old and sits in Northern Neck in Virginia on a beautiful estate. There is no food for purchase but you are welcome to bring your own. The lawn is sprawling and chairs are welcome.

The Hague Winery, Hague, VA - The Hague Winery, in the Northern Neck of Southern Virginia, is a small family business since 2004. The tasting room is housed in a former barn overlooking the manor home, outbuildings, vineyards and surrounding farmland. Reviewers offer that is just what the doctored order in tranquility.

Williamsburg Winery, Williamsburg, VA - The Williamsburg Winery is part of Wessex Hundred and is also home to a 300 acre farm with a hotel and 2 restaurants. Don’t forget the wine shop for purchase!

Virginia Eastern Shore

Bloxom Winery, Bloxom, VA - This winery/bistro combination serves fabulous wine and divine pizza. With a covered patio, this is a Saturday afternoon dream.

Chatham Vineyards, Machipongo, VA Chatham Farm has been a working farm for four centuries and sits at the mouth of Church creek. Plenty of outside seating overlooking the fields.

Wineries Located in the Southern Maryland

Fridays Creek Winery, Owings, MD - Fridays Creek is a lovely winery in pretty barn with an art gallery on the upper floor. The grounds are lovely and the tasting room is charmingly rustic.

Perigeaux Vineyards and Winery, Saint Leonard, MD- Situated near the Chesapeake Bay and across from Taylors Island on a 27-acre farm. They have a small selection of both reds and whites.

Romano Vineyard and Winery, Brandywine, MD - Romano Vineyard and Winery is located south of Washington, DC and easy for a quick drive from the Nations Capital.

Slack Winery, Ridge, MD - Tucked away in the southern end of Maryland, the award winning Slack wines are located on a large farm with great southern charm. You can relax, drink wine and bring your own food.

Port of Leonardtown Winery, Leonardtown, MD- Fabulous wine and a great rotating food truck each night. They have a great line of sweet wines including one called Black Forest Cake – Yum!

Bordeleau Vineyards and Winery, Salisbury, Maryland- Located just south of Salisbury, Maryland, nestled between the gentle slopes of the Wicomico Creek. Bordeleau means "The Water's Edge" and gives the winery a peaceful feel, especially if you hang out on the dock.

Solomons Island Winery, Lusby, MD - Solomons Winery was founded in the fall of the year 2002. You are able to sit outside and watch the water and sun over the bridge with your wine and dog.

Cove Point Winery, Lusby, MD - Cove Point Winery is a small micro-winery located in Southern Maryland. Visitors love the price and availability of wines.

Wineries Located in the Bay Bridge Region

St. Michaels Winery, St Michaels, MD - St. Michael's tasting room is located in the middle of downtown St. Michael’s. You can shop, sight see and eat all while checking out new wines.

Far Eastern Shore Winery, Easton, MD - Far Eastern Shore Winery is boutique winery specializing lightly sweet, fruit flavored wines. They also have dessert wines for a nightly cap off.

Great Frogs Winery, Annapolis, MD - Great Frogs Winery is a hidden gem in Annapolis. The setting is quaint and romantic, a place where the locals seem to hang out and enjoy some great wine.

Layton's Chance Vineyard, Vienna, MD - Located off highway 50, Layton’s offers music during Happy Hour on a Friday night. You can bring a picnic and sit outside for the Concerts in the Country Series. Even dogs are welcome in our picnic area!

Thanksgiving Farm Winery, Harwood, Maryland - Thanksgiving Farm Winery specialized in the production of European Style dry wines. Of the may reviews they get is their outstanding hospitality.

Triple Creek Winery, Cordova, MD - Triple Creek Winery is a endeavor of four brothers from a family of full-time farmers. They have a updated tasting area barn and possess the wonderful greeting team, their 2 dogs, to lead you in! Absolutely dog friendly.

Wineries Located in the North Bay

Tilmon's Island Winery, Sudlersville, MD - Located on Maryland's Eastern Shore near the Delaware State Line, Tilmon's Island Winery is a boutique winery, producing in small quantities. They have growing and producing since 2004 but not on an island.

Boordy Vineyards, Hydes, MD- Boordy is located in Northern Maryland and has been in the wine/agriculture business since 1965. Treat yourself to an afternoon in the country and settle into the charming wine cellar or outdoor patio for quiet conversation or even a celebration.

Cassinelli Vineyards and Winery, Church Hill, MD - Located on your way to Chestertown, Maryland on the Eastern Shore with 110 acres of woods and rolling, open land. Cassinelli Winery & Vineyards has been growing since 2004.

Cascia Vineyards, Stevensville, MD - Mark Cascia Vineyards grows 12 acres of premium wine varietals on Kent Island on Maryland's Eastern Shore. The vineyard overlooks the waters of the Chesapeake Bay and is simple breathtaking.

Chateau Bu-De, Chesapeake City, MD - The family owned vineyard & winery is located on 368 acres in Chesapeake City, Maryland. Chateau Bu-De vineyard & winery has become the premiere location for fine wines and has a beautiful building and grounds overlooking a river view - a very nice setting to enjoy their wine and lite food offerings.

Crow Vineyard and Winery, Kennedyville, MD -Crow Vineyard and Winery is a 365 acre working farm, with a Farmstay B&B, winery, tasting room, cattle and horses just north of Chesterfield, MD on the Eastern Shore.

Dove Valley Winery, Rising Sun, MD - On the very north part of the Chesapeake Bay sits Dove Valley. A family run vineyard with rave reviews on experience, price, selection, and knowledge.

Mount Felix Vineyard and Winery, Havre de Grace, MD -Vineyards is based in a 1830s estate with great views of the Chesapeake Bay and Susquehanna River.