best eastern shore maryland wineries vineyards

The Eastern Shore of Maryland is a popular destination year round. This area is renowned for its excellent opportunities for swimming, boating, biking, and bird watching. What many people don’t know is that the Maryland Eastern Shore wineries are also popular to visit. Let’s take a look at the best Maryland Eastern Shore wineries which may even be some of the best in the United States.

Maryland Eastern Shore Wineries

Whether you want to sample dry wines that are crisp from the very first sip, or you are looking for a fruit forward red wine, the local wineries in Maryland’s eastern shore have something for each unique palate. While Virginia is famous for the Chesapeake Wine Trail, the small towns of the Chesapeake Bay on the Maryland side also make for a wonderful getaway from busy city life in Washington DC and Baltimore

Far Eastern Shore Winery

The Far Eastern Shore Winery is a Maryland Vineyard that embodies the quintessence of a family-owned, boutique micro-winery. Located in the historic town of Easton on Maryland’s Eastern Shore, it is renowned for its unique approach. The winery specializes in non-traditional fruit-grape wine blends that cater to a diverse range of palates. 

With a focus on creating gently sweet wines, Far Eastern Shore Winery has garnered attention for its distinct offerings. The winery operates on a reservation basis for large groups and is open to visitors looking for a personalized wine-tasting experience. 

Need To Know: Little outside space

Food: Call to inquire


Location: 8370 Ocean Gateway, Easton, MD 21601

Bordeleau Winery

The Bordeleau Winery is located along Wicomico Creek just south of Salisbury, Maryland. The winery is known for its Maryland-made wines and invites visitors to relax among the beauty of the estate, enjoying world-class wines and an abundance of wildlife.

The winery’s Tasting Room is located on Talbot Street in St. Michaels, provides a cozy and relaxed atmosphere for guests. Here, visitors can indulge in award-winning wines at the tasting bar, lounge indoors, or enjoy the great outdoors at the patio and picnic areas. The winery is open year-round, and its friendly staff is always welcoming to visitors.

Most importantly, Bordeleau Winery is family-friendly, making it an ideal destination for those looking to enjoy a wine-tasting experience with the whole family. The winery offers a unique opportunity to learn about the winemaking process and savor a variety of their white wines, from sauvignon blanc to bold reds.

Need To Know: Kid friendly, open year round

Food: Snacks and select foods are available for purchase


Location: 3155 Noble Farm Road, Eden, Maryland 21822

Triple Creek Winery

This family owned vineyard was started by 4 brothers and you truly do feel a sense of family when visiting this family business. There are mixed reviews online about the winery not always being open. Be sure to call ahead of time to make sure that you can visit this winery, especially if you are making the drive out to the wine regions of the Eastern Shore. 

Need To Know: Kid friendly

Food: Check website as well as call to find out, little information available online


Location: 11138 3 Bridge Branch Rd, Cordova, MD 21625

Layton’s Chance Vineyard & Winery

Layton’s Chance Vineyard & Winery, spanning over 14 acres in the scenic landscape, is a family-owned vineyard that offers a diverse range of wines and a relaxing atmosphere for visitors. Located on part of a 1,800-acre family farm, the winery features a Tasting Room open daily, along with weekend tours of their 15-acre vineyard. The vineyard is equipped with walking trails, a play area, and ample picnic space, making it an ideal location for a day out.

The vineyard encourages visitors to enjoy a “Lazy Day” by walking the nature trails, relaxing in the picnic areas, and touring the farm and vineyard. It offers a variety of wines including reds, whites, sweet and dry options, and a house Rosé made with 100% Layton’s Chance Chambourcin grapes. Moreover, the vineyard hosts special events such as live music sessions on Friday nights and Concerts in the Country Series, where guests can bring their picnics and enjoy the outdoor ambiance.

Need To Know: Good outdoor space for walking and to picnic

Food: Can bring a picnic


Location:  4225 New Bridge Road, Vienna, MD 21869

Slack Winery At Slack Farms & Woodlawn Farms

Slack Farms in Maryland encompasses several elements, each offering a unique experience. First, there is Slack Winery & Jubilee Farm. This is located in Leonardtown, MD.

Slack Winery specializes in Italian-method wines that are specifically designed to pair well with Maryland seafood. The wines are produced at Jubilee Farm, a 139-acre farm that provides a picturesque setting for wine lovers.

Next there is Woodlawn Farm. This is a historic estate that dates back to 1634, originally granted by Cecil Calvert to his son, Leonard. The Slack Farms Foundation supports Woodlawn Farm and it focuses on providing internships and apprenticeships for local and international students. These students engage in various projects at the farms, gaining practical experience in agriculture and related fields.

Many people may not know that Slack Farms leads the “Walk the Farms” program. This program is in partnership of small farms that invite visitors to experience the tradition of walking through a farm. The initiative is led by Slack Farms and it is supported by a grant from the Maryland Department of Commerce Office of Tourism.

Need To Know: Kid friendly

Food: Check website or call to find out


Location: Woodlawn Farm 16040 Woodlawn Dr, Ridge MD 20680

Jubilee Vineyards & Winery

Jubilee Vineyards & Winery has formal gardens and vineyards. Located on the Eastern Shore of Maryland, the deed to the farm dates from 1737. In addition to being a winery, this saltwater farm also hosts events. Wedding ceremonies and receptions can be accommodated for up to 200 at the Winer Barn. The rustic Amish-built barn contains oak barrels and steel tanks amid draped garden lights lights for a completely authentic winery wedding. 

Need To Know: Can accomodate groups and host events

Food: Check website or call for more information


Location: 19860 Pear Hill Rd, Leonardtown MD 20650  

Cascia Vineyards

Cascia Vineyards has a beautiful setting for wine tasting. It is located right on the water and has unforgettable views. Especially on warm days, this Southern Maryland winery is an excellent place to spend a Saturday or Sunday afternoon. The owners, Mark and Kim Cascia, are known for their gracious and friendly approach, making guests feel welcome. 

Need To Know: Only open on weekends, family friendly.

Food: Call to ask


Location: 1200 Thompson Creek Rd, Stevensville, MD 21666

St. Michael’s Vineyard

St. Michael’s Winery is located in the picturesque and historic waterfront town of St. Michaels, Maryland. It was established in May 2005 by two couples living in Saint Michaels, the winery crafts its wines from carefully selected grapes sourced from specific growers. They also maintain a modest vineyard in nearby Wye Mills, which has produced their first all-Maryland wine, a dry, light white called Long Splice. 

Most of their wines are available in small runs of 250 cases or less, adding an exclusive touch to their offerings. The winery is situated in the Historic Old Mill District of St. Michaels, which is conveniently within walking distance of many shops and restaurants. 

Need To Know: Small tasting room, family friendly.

Food: Call to ask


Location: 609 South Talbot Street, St. Michaels, MD 21663

Cove Point Winery

Cove Point Winery is located in Lusby, Maryland. This Calvert County winery is also very close to Cove Point Beach and the Cove Point Lighthouse. It’s a small place with limited parking, but the yummy wine makes it worth the trip. There is limited indoor seating. Although they may allow kids, it may not be the most relaxing winery experience for the adults due to the limited space. 

Need To Know: Small but friendly

Food: Call ahead to inquire about food


Location: 755 Cove Point Road Lusby, Maryland 20657

Love Point Winery

Very close to Annapolis is Love Point Winery. If you are a wine lover who also loves water views, then this is the perfect winery for you. 

Love Point Winery is located on Maryland’s Eastern Shore on Kent Island. It was established in 2015. It’s an ideal destination for family and friends to relax and enjoy local wines.

The winery is kid-friendly and pet-friendly, welcoming guests to bring their own picnics, though outside food and drink are not permitted. They offer charcuterie and veggie boards as dining options. 

Love Point Winery operates Wednesday through Friday from 1 pm to 8:30 pm, Saturday from 11 am to 8:30 pm, and Sunday from 11 am to 6 pm. Walk-ins are welcome, but reservations are preferred, typically lasting around two hours

Need To Know: Reservations are preferred

Food: Some food and snacks available for purchase


Location: 305 River Shore Lane, Stevensville, MD 21666

Other popular wineries in Maryland include Black Ankle Vineyards, Basignani Winery, Chatham Vineyards, Big Cork Vineyards, and Mount Felix Vineyard. While these are located in Maryland, they are much closer to Baltimore than they are to the eastern shore of Maryland.

Maryland Eastern Shore Wineries: Summary

There is a wonderful world of wine to explore in the state of Maryland and even more specifically on the eastern shore. There are wineries in nearly every part of Maryland from east to west and enjoying local wines is a prominent part of Maryland culture. Traveling past the wineries that are near Annapolis area, there are many wineries that are part of the welcoming spirit of the Eastern Shore of Maryland.

From white wines to red wines and rose wines, there are a number of wineries on the Eastern Shore of Maryland that you can discover. Many people don’t realize that Maryland’s wine industry is quite robust. Even outside the eastern shore, the state of Maryland has many popular wineries all over. The Eastern Shore wineries also have the charm of the scenic Chesapeake Bay in addition to great wines.

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