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Exploring Wineries and Wine Bars in Annapolis, Maryland

Great Frogs Winery

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Annapolis, Maryland, is not only known for its rich history and maritime culture but also for its vibrant wine scene. The city offers a variety of wineries and wine bars that provide unique and memorable experiences for both locals and visitors. Whether you’re a wine connoisseur or simply looking to enjoy a relaxing evening, Annapolis has something to offer. This guide highlights some of the best wineries and wine bars in Annapolis, ensuring you make the most of your visit.

Top Wineries in Annapolis

Great Frogs Winery

Just minutes from downtown Annapolis, Great Frogs Winery offers wine lovers a rustic and charming setting. This boutique winery is situated on a historic tobacco farm, providing a picturesque backdrop for wine tastings. Great Frogs specializes in handcrafted wines made from locally grown grapes, ensuring a unique taste of Maryland’s terroir. Visitors can enjoy guided tastings, wine flights, and special events throughout the year.

Thanksgiving Farm Winery

Located in Harwood, just a short drive from Annapolis, Thanksgiving Farm Winery is a family-owned vineyard dedicated to producing high-quality wines. The winery focuses on traditional French winemaking techniques, resulting in elegant and refined wines. Thanksgiving Farm offers tastings by appointment, allowing guests to experience their wines in an intimate and personalized setting. The picturesque surroundings and warm hospitality make it a perfect destination for wine enthusiasts.

Top Wine Bars in Annapolis

Red Red Wine Bar

Situated on Main Street, Red Red Wine Bar is a cozy and stylish spot known for its extensive wine list and relaxed atmosphere. The bar offers a wide selection of wines from around the world, as well as a variety of local Maryland wines. Guests can enjoy wine by the glass, bottle, or through curated wine flights. The menu also features delicious small plates and entrees, making it a great place for a casual meal or a special night out.

BIN 201 Wine Sellers

BIN 201 Wine Sellers is a premier wine bar and retail shop located in the Annapolis Towne Centre. Known for its knowledgeable staff and carefully curated wine selection, BIN 201 offers a sophisticated yet approachable wine-tasting experience. The bar hosts regular wine tastings, educational events, and wine dinners, providing opportunities for both novice and seasoned wine lovers to expand their palates. The inviting ambiance and expert guidance make BIN 201 a must-visit destination.

Cooper’s Hawk Winery & Restaurant

Cooper’s Hawk Winery & Restaurant combines a modern dining experience with a winery’s charm. Located at the Annapolis Towne Centre, this establishment offers a unique blend of upscale dining and wine tasting. Cooper’s Hawk features an extensive wine list, including their own award-winning wines. Guests can enjoy tastings at the Napa-style tasting room or pair their meal with expertly selected wine flights. The restaurant’s stylish setting and exceptional service make it a standout choice for wine enthusiasts.

Smashing Grapes Kitchen + Wine Bar

Smashing Grapes Kitchen + Wine Bar brings a touch of Napa Valley to Annapolis. This chic and contemporary wine bar offers an impressive selection of wines from around the world, along with craft cocktails and a diverse food menu. The bar’s wine-tasting flights and pairing dinners provide a delightful culinary experience. Smashing Grapes also hosts regular events and live music, creating a lively and enjoyable atmosphere for guests.

Special Experiences and Events

Wine Tasting Events

Annapolis’s wineries and wine bars frequently host special events, including wine tastings, pairing dinners, and seasonal celebrations. These events offer unique opportunities to sample a variety of wines, learn from expert sommeliers, and enjoy gourmet cuisine. Keep an eye on event calendars to make the most of your visit.

Private Wine Tours

For a more personalized experience, consider booking a private wine tour. Many wineries and wine bars in Annapolis offer private tastings and tours, allowing you to explore their offerings in an exclusive setting. Whether celebrating a special occasion or seeking a unique outing, private tours provide a memorable and tailored experience.

Outdoor Wine Experiences

Several Annapolis wineries offer outdoor tastings and events, perfect for enjoying Maryland’s scenic beauty. From vineyard tours to alfresco wine dinners, these experiences combine great wine with the charm of the outdoors. Great Frogs Winery and Thanksgiving Farm Winery are particularly noted for their picturesque outdoor settings.

Interested in other outdoor experiences, check this article:

Planning Your Wine Adventure

Choosing the Right Venue

When planning your visit to Annapolis wineries and wine bars, consider your preferences for wine styles, ambiance, and location. Whether you prefer a rustic vineyard setting, a stylish downtown wine bar, or a modern dining experience, Annapolis has venues to suit all tastes.

Booking in Advance

Many wineries and wine bars, especially those offering private tours or special events, require advance reservations. Booking ahead ensures you secure your spot and allows the venue to provide the best possible experience. Check their websites or contact them directly for availability and booking information.

What to Bring

To enhance your wine-tasting experience, consider bringing the following:

  • Comfortable Attire: Dress appropriately for the venue and weather, especially if you plan to explore outdoor vineyards.
  • Notebook or Wine App: Keep track of the wines you enjoy and any notes on tasting profiles.
  • Designated Driver: If you plan to visit multiple wineries or enjoy several tastings, ensure you have a designated driver or use a transportation service.

Respecting the Venue

Remember to respect the venue’s rules and guidelines, including policies on outside food, pets, and children. Being courteous and considerate enhances your experience and ensures a pleasant visit for all guests.


Annapolis, Maryland, boasts a vibrant and diverse wine scene, offering a range of experiences for wine lovers. From charming wineries like Great Frogs and Thanksgiving Farm to stylish wine bars such as Red Red Wine Bar and BIN 201, there’s something for everyone to enjoy. By planning your visit and exploring the unique offerings of each venue, you can create memorable and delightful wine-tasting adventures in this historic city.


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