How to Travel Chesapeake Wine Country

The main artery of Chesapeake Wine Country is the Chesapeake Wine trail of 16 wineries paralleling the rivers and creek tributaries of the Chesapeake Bay.
(see map)

Some say its possible to take in all the wineries during a long holiday weekend. But experiencing the countryside, small towns and B&B's spanning 6 counties and 125 miles is as much a part of enjoying wine country as sipping artisan wines at the wineries themselves. Enjoy our "How to travel Chesapeake Wine Country Series" shown right.

  • Travel the whole Trail through Chesapeake Wine Country 4 DAYS Open or Close

    Take in all the Chesapeake Wine Trail Wineries

    Coming from Points North? Philadelphia, Wilmington, Middletown, DE, Harford County, MD...Travel the whole trail! or in reverse!

    notes: Best to do this trip late spring through fall when wineries are more apt to be open. (see trail winery hours) You will start your trip at Dove Valley Winery the northernmost winery on the trail and end your travel at Bordeleau Winery outside of Salisbury. Want to go further? Take in the Maryland Wine Bar in the charming town of Berlin, 30 minutes due east of Salisbury on the way to Ocean City, Maryland.

    The Whole Trail in 4 days Itinerary

    Day 1 Thursday

    11 am Dove Valley Winery in the midst of Mennonite Country minutes from I95
    1:30 pm Turkey Point Vineyard Tasting Room in the charming town of North East
    4:30 pm Chateau BuDe Historic Farm and Winery
    Overnight Farmstay B&B Crow Vineyard & Winery

    Day 2 Friday

    8:00 am B&B farm experience at Crow Farm
    12:00 noon Crow Vineyard & Winery Wine Tasting Room
    3:00 pm Chestertown visit Cassinelli Distilling and Wine Bar
    Overnight at Brampton Inn - Wine Friendly B&B

    Day 3 Saturday

    9 am Chestertown Farmers Market to enjoy tastings from Tilmon Island Winery and Clovelly Vineyards
    (optional: 11 am Appointment at Vineyards at Dogwood for tasting
    1 pm Cascia Winery Tasting Room
    4 pm Wine tasting at Triple Creek Winery
    Overnight St. Michaels B&B

    Day 4 Sunday

    11 am Wine Tasting St. Michaels Winery
    (optional by appointment Little Ashby Vineyards
    1:30 pm Laytons Chance Vineyard & Winery - enjoy walking trails and a gift shop
    4:00 pm Bordeleau Winery- water's edge elegant winery

    For more info:

    See winery website links here

  • Travel Chesapeake Wine Country North 1 DAY Open or Close

    A Town and Country break from I95: Traveling Chesapeake Wine Country North

    note: You must schedule this trip Thursday through Monday to visit the two wineries spotlighted. See winery trail hours here

    If you are traveling the top of the Chesapeake Bay whether on the way to I95, Wilmington or wanting to take a break from this mid-Atlantic corridor try wine country north.

    Dove Valley Vineyard and Winery is just minutes from I95 exit 93. Nestled in Mennonite country, during your drive to the winery you'll likely see lots of buggies, local produce and raw country scenery. You can complement a visit to this Woodstock like winery which has on-site events like live dinner theatre and concerts such as Beatles Tributes with a visit to the town of Northeast about 15 minutes away. On main street is Turkey Point Vineyard's Wine Tasting Room. Stay for dinner at this boating town there are plenty of restaurants or take a hike to the Turkey Point Lighthouse at Elk Neck State Park and get an amazing view of the Susquehanna River down the bay. On your drive to the park you'll pass Turkey Point's Vineyard and you'll pass Hart's Amphitheater next to an old church offering a place to sit and view the expanse of the bay as well.

    Suggested Itineraries

    Hike Turkey Point

    Midday Wine Tasting at Dove Valley Vineyard and Winery

    Afternoon Hike Turkey Point Lighthouse

    Walk the town of Northeast

    Wine Tasting Turkey Point Tasting Room

    Dinner town of North East

    notes: suggested days are Thursday through Monday

    Dinner Theatre at Dove Valley

    Walk the town of North East

    Wine Tasting at Turkey Point Vineyard

    Travel to Dove Valley Winery for Wine Tasting

    Dinner Theatre at Dove Valley

    notes: check Dove Valley's website for schedule of live theatre performances

    For more info:

    Dove Valley Winery
    Turkey Point Vineyard

  • Travel Chesapeake Wine Country Farmstay B&B Destination OVERNIGHT 1 DAY Open or Close

    Enjoy a state of the art winery, farmstay B&B at an authentic working farm

    note: You can schedule this trip to Crow Vineyard & Winery any day as they are open 7 days a week almost year round. See winery trail hours here

    If you are visiting the charming historic town of Chestertown or heading south from the Philadelphia/Wilmington area a visit to this diversified farm now award winning winery is quite an experience and easily accessible.

    Crow Vineyard and Winery is located on a 3rd generation farm just 20 minutes north of the popular Eastern Shore town of Chestertown and the same drive south from the bustling suburban town of Middletown, Delaware, 30 minutes off I95. The Crow's offer wine country travelers a unique experience, a chance to enjoy B&B amenities while experiencing life on an authentic working farm, getting up close and personal with a herd of grass-fed angus cattle, gathering eggs from the chicken coup and enjoying events and music at the haybarn. But there's more ....this farm is also a state-of-the art winery complete with bottling infrastructure and a wine tasting room remodeled from an old milking barn. The Crows have a full time wine maker on staff and offer events almost every weekend.

    Suggested Itinerary

    Farmstay Overnight Visit and Wine Tasting

    Farm chore tour with owners

    B&B breakfast

    Country hike through the farm land to view angus herd

    Wine Tasting at noon

    Head to Chestertown for dinner

    For more info:

    Crow Vineyard & Winery
    Events at Crow Vineyard & Winery

  • Travel Chesapeake Wine Country Bay Gateway Sip 1 DAY Open or Close

    Heading to the Eastern Shore of Maryland traveling the Bay Bridge? Take a Wine & Spirits Break.

    note: You can schedule this trip to Cascia Vineyards on weekends noon to 4 pm, April through late fall. See winery trail hours here

    Cascia Vineyards is just off the Bay Bridge on Maryland's Eastern Shore.

    Mark Cascia is a Nasa Engineer by day and an astute self-taught wine maker. He enjoys personally serving his guests and telling them how he makes his wine. His motto "I like to make wines for everyone."

    This beautiful vineyard is sedate and quiet with a creekside setting. The light filled wine tasting room has a porch with an expansive water view.

    A visit at this winery is a perfect place to get a taste of the Eastern Shore while you take a break in your travels to the shore whether to the beaches or the charming towns of Chestertown and St. Michaels.

    Suggested Itinerary

    Wine & Spirits

    Visit Cascia Vineyards and then take in Blackwater Distilling about 15 minutes or less away also open weekends noon through the afternoon. Either head back home or enjoy dinner in historic Stevensville at Rustico Restaurant and Wine Bar (great homemade pizzas!)

    Cascia Vineyards
    Rustico Restaurant and Wine Bar