Monthly Archives: April 2017

A Chesapeake Wine Trail Escape is Everything you Need This Weekend

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The Waves at the Chesapeake Shore

Slowly tease the pebbly beach as the sun dips behind the Bay Bridge. You sip on a local rosé, twirling an oyster shell in your palms as you laze in a Cape Cod chair. A slow inhale…your eyes crescent moons as the salty breezes washing over you.

“What an incredibly relaxing moment…” the thought rolls around as you finish the last of your crisp and fruity apertif.

The Maryland wine country awaits you and you’re ready for a relaxing weekend of discovery, adventure, friendships, and most importantly, lots and lots of vino.

Maryland is rife with wine trails, but being the adventurous spirit that you are, you’re itching to check out the road less traveled. The northeastern part of the state—on the other side of the Chesapeake Bay— is a lesser explored wine coun- try that is dotted with brick colonials, quaint wineries, and hearty local fare. It’s the perfect place to escape for a weekend and sample some local wines.


Maryland is in the northeastern part of the country. If you are flying in, chances are you will be landing at the Baltimore/Washington International Thurgood Marshall Airport, located centrally in the state. There is no public transportation in the Chesapeake wine trail region, so you will want to rent a car when you land.

Driving: If you are coming from the:

North: I-95 from Wilmington, DE or rte 213 from PA

South: I-95 from Richmond, VA

East: US-301 through Warwick, DE

West: Rte 50 from Washington, D.C.

BWI Airport: I-97 to Rte 50

Chesapeake Bay Bridge

The Chesapeake Bay is Maryland’s famous expanse of water with a dual-span bridge that connects the eastern and western part of the state. It also separates the state’s rural Eastern Shore region with the urban Western Shore. Built in 1952, the bridge spans over 4 miles and is still one of the longest continuous over-water steel structures in the world.-

You hit land again once you reach Kent Island, 3/4 of the way over the bay. Check out Terrapin Beach Park for prime places to snap a pic of the bridge in all its glory. The 276-acre park features scenic views and a 3.5-mile oyster chaff walking trail that is brilliantly speckled with tide pools and wildflower meadows.

Stop and Enjoy

By now you have probably worked up an appetite from your trip. Kent Island is the perfect place to stop and enjoy one of the main staples that Maryland is famous for—crab.

The Fisherman’s Seafood Market and Crab Deck is a typical New England pier boasting rows of boats docked at the waterfront restaurants, and a fresh seafood market. Don’t leave before you get your first taste of the local wines and your hands dirty with a bucket of crabs.

The Great Oaks

Another 45 minutes north and you’ve hit your first spot to hunker down on your trip. Much like most places to stay in MD wine country, the Great Oak Manor is a beautiful brick Georgian-style bed and breakfast right on the water. The 12-guestroom country-style estate is pet-friendly and serves breakfast every morning.

If you are looking for something a little more upscale, the Mears Great Oak Landing is a stone’s throw away from the B&B. Mears is a 28-room lodge and marina resort with a restaurant, six-hole golf course, and a boat dock. Check out Jellyfish Joel’s Beach Bar on the resort’s sandy shores if you want to end the night with a bang.


Fuel up with breakfast at the Great Oaks and get ready to continue your Chesapeake Bay wine tour. A 20-minute drive south on the 213 will take you to the first winery on your stop—Cassinelli’s.

Cassinelli Winery & Vineyards

Along the shores of the Chester River lies the family owned Cassinelli Winery & Vineyards. The boutique winery and distillery is the perfect spot to start your wine tour with a 100-acre farm boasting grape varieties like Merlot, Chardonnay, Viognier, Malbec, Petit Verdot and San Giovese vines.

The winery tasting fee is $8 and the tasting room is open M, F, Sa, Su, at 11:30 am (closing hours vary). Try their deliciously popular 2010 Rosé of Barbera, a crisp wine with strawberry flavor notes and the Bronze medal winner of the Governer’s Cup. For a dryer wine, try the 2010 Vidal, a sweet white with fruity overtones.

Keep in mind, this winery does not serve food, so when you’ve worked up an appetite, head over to the Lemon Leaf Cafe in downtown Chestertown. The homey, quaint outpost serves up sandwiches, steak, pasta, and of course, seafood. Their Baked Crab Imperial is to die for, but they also have a ton of salads too.

At this point, you may want to unload at your lodging for the night, as the rest of the day will unfold in downtown Chestertown.

Crow Farm

Once you get to the point where your even-keeled buzz is evolving into naptime, Crow’s Farm is your haven for rest and relaxation. Owned by the Crow family, the 365-acre farm and winery offer rooms with antique decor and a hearty breakfast in the morning. And if you’re up for it, they also have a tasting room of their own. Besides, you can sleep when you’re dead, right?

Try these award winners on for size:

2015 Barbera Rosé -Double Gold – Governer’s Cup

2014 Chardonnay -Bronze – Governer’s Cup

2015 Vidal Blanc -Gold – International Women’s Wine Competition

To Do:

Once you’re heading back into town (it’s about a 15 minute drive), now’s the time to consider some fun activities outside of drinking (you wino). There are several things to do in downtown Chestertown:

Day: The Chestertown Historic District is home to a plethora of art galleries and small boutiques that you can peruse to your heart’s content. Stop in to some of these galleries in the area for some impressive artwork:

o The Tree of Life Gallery

o The Artist’s Gallery

o Hegland Glass

Night: The Garfield Center for the Arts at the Prince Theater holds a variety of shows throughout the week from plays to concerts, and even an open mic. Most of the shows start at around 7 p.m. so dinner is either going to be early or late.

Chester River Wine & Cheese Co.

All of these stops are within walking distance, so it only makes sense for you to mosey on over and check out the Chester River Wine & Cheese Co. Located a block south of Cassinelli’s in the vibrant arts district, the boutique is a specialty market that serves domestic wines, cut-to-order cheese, charcuterie and pate, as well as gourmet foods like handmade jam, mustard, salts, olive oils, and vinegars.


If you skip breakfast at the farm, you may want to grab a light lunch at Café Sado before you hit your last winery. The chic setting serves a broad menu of sushi, Thai, and Ameri- can fare—not to mention a reasonable selection of local wines (and of course sake—it is sushi after all).

Clovelly Vineyard

The last winery on your tour, Clovelly is known for it’s bountiful vineyards and lolling hills neatly hugged by a bend in the Chester River. As they themselves proclaim “Our wines are borne from the rich earth and the warm river breezes.” Established in the 1950’s, this third-generation winery knows what they’re doing.

Clovelly offers vineyard tours and tastings starting at $10 and they require an appoint- ment. Guests get to keep a souvenir glass as they sample 6 of the vineyard’s refreshing varietals. Try their citrusy 2015 Traminette or their 2013 Devils Reach with chocolate and cherry flavor notes.

Crossing over the bridge on your way home, Sandy Point State Park is the perfect stop to end your trip. The 786-acre state park has a variety of trails and stops to get the last of the vacation selfies out of your system.

As you watch the sparkling sun set like a jewel across the expansive Chesapeake Bay—the last tastes of Clovelly still on your breath—you think to yourself “this is exactly what I needed.”

As you watch the sparkling sun, set like a jewel across the expansive Chesapeake Bay—the last tastes of Clovelly still on your breath—you think to yourself “this is exactly what I needed.”

Chesapeake, Maryland awaits you.


Crow Farm: 12441 Vansant Corner Rd, Kennedyville, MD 21645 | (302) 304-0551

Cassinelli Winery & Vineyards: 323 High St, Chestertown, MD 21620 | (410) 556-6825 Chester River

Wine & Cheese Co.: 117 S Cross St, Chestertown, MD 21620 | (443) 282-0220 The Clovelly

Vineyard: 301 Clovelly Lane, Chestertown, MD 21620 | (410) 708-1775

Triple Creek Winery: 11138 Three Bridge Branch Road, Cordova, MD 21625 | (410) 924-4190

Great Frogs Winery: 3218 Harness Creek Rd, Annapolis, MD 21403 | (410) 626-6193

Boordy Vineyards: 12820 Long Green Pike, Hydes, MD 21082 | (410) 592-5015
BONUS: This winery is located just north of Baltimore, perfect for locals or anyone travelling south from Pennsylvania or New York!

Places to Eat

Luisa’s Cucina Italiana: 849 Washington Ave, Chestertown, MD 21620 | (410) 778-5360

Blue Heron Café: 236 Cannon St # 1, Chestertown, MD 21620 | (410) 778-0188

Uncle Charlie’s Bistro: 834 High St, Chestertown, MD 21620 |(410) 778-3663

Nonna Maria’s: 5306 Church Hill Rd, Church Hill, MD 21623 | (410) 556-6171

The Kitchen at The Imperial: 208 High St, Chestertown, MD 21620 | (410) 778-5000

Café Sado: 870 High St, Chestertown, MD 21620 | (410) 778-6688

Fish Whistle: 98 Cannon St, Chestertown, MD 21620 | (410) 778-3566

Place to Stay

Crow Farm: 12441 Vansant Corner Rd, Kennedyville, MD 21645 | (302) 304-0551

Great Oak Manor: 10568 Cliff Rd, Chestertown, MD 21620 | (410) 778-5943

Brampton B&B Inn: 25227 Chestertown Rd, Chestertown, MD 21620 | (410) 778-1860

Inn at Mitchell House: 8796 Maryland Pkwy, Chestertown, MD 21620 | (410) 778-6500

Imperial Hotel: 208 High St, Chestertown, MD 21620 | (410) 778-5000

Mears Great Oak Landing: 22170 Great Oak Landing Rd, Chestertown, MD 21620 | (410) 778-2101

White Swan Tavern: 231 High St, Chestertown, MD 21620 | (410) 778-2300


Garfield Center for the Arts at the Prince Theatre: 210 High St, Chestertown, MD 21620 | (410) 810-2060

Flow Salon Spa: 305 High St, Chestertown, MD 21620 | (410) 810-1881

Ennisbrook Farm Equestrian Centre: 2201 Bennett Point Rd Queenstown, MD 21658 | (410) 739-6266