When winter rolls into Annapolis, it brings more than just crisp air and festive cheer—it sets the perfect scene to enjoy the best winter cocktails in Annapolis. From bold, whiskey-infused creations to sweet, cozy concoctions, this charming city offers a variety of cocktail experiences that capture the essence of the season. Let’s take a closer look at the top spots serving up these irresistible seasonal beverages.
1. Sailor Oyster Bar
Sailor Oyster Bar is a go-to destination for winter cocktails with a creative twist. Their mixologists masterfully combine traditional flavors with innovative techniques to craft drinks that delight the senses. Whether you’re trying their seasonal specials or requesting a personalized blend, Sailor Oyster Bar promises a memorable experience.
2. Dry 85
Known for the best winter cocktails in Annapolis, Dry 85 stands out with its robust menu. From bold whiskey blends to comforting sweet drinks like “What the Dill” and “Chocolate Crover,” every cocktail is crafted with precision. Pair your drink with hearty comfort food to make your visit even more satisfying.
3. Kilwins
For those with a sweet tooth, Kilwins is a winter wonderland. Their dessert-inspired cocktails feature rich flavors like dark chocolate, caramel, and peanut butter, delivering a warm, indulgent treat. This spot is perfect for anyone who loves their cocktails with a sweet, decadent twist.
4. Fox’s Den
Fox’s Den offers a gastropub atmosphere where handcrafted cocktails take center stage. Their drinks, made with fresh juices and creative garnishes, cater to both flavor enthusiasts and health-conscious patrons. Cozy and inviting, it’s an ideal spot for enjoying seasonal delights.
5. Red Red Wine Bar
With its vibrant ambiance and expertly crafted drinks, Red Red Wine Bar is a favorite for the best winter cocktails in Annapolis. Their signature Sangria Smash and Espresso Martini are standout options, complemented by warm decor and exceptional service, making it a top spot for holiday gatherings.
6. Chart House
Chart House combines stunning waterfront views with a menu of seasonal favorites like warm spiced cider and the Coconut Ginger Lemon Drop. The scenic setting paired with expertly crafted cocktails ensures a delightful winter experience for locals and visitors alike.
7. Middleton Tavern
Middleton Tavern blends history and hospitality with a menu full of crowd-pleasing cocktails. Seasonal creations like Cranberry Bliss and Lemon Delight, alongside signature oyster shooters, make this tavern a must-visit. Pair the drinks with live music and delectable seafood for an unforgettable evening.
8. Preserve
Preserve is a haven for cocktail lovers who appreciate locally sourced ingredients and artisanal craftsmanship. Winter favorites like Cranberry Puree and Iris Blanco Vermouth showcase their creative approach to mixology, ensuring each sip is as memorable as the setting.
9. Level
Level redefines the cocktail experience with handcrafted drinks and inventive flavor combinations. Signature offerings like the Level Original Gimlet and Honey Beer shine on their thoughtfully curated winter menu. The cozy, wood-accented interiors make it a perfect place to unwind with the best winter cocktails in Annapolis.
10. Reynold Tavern
Reynold Tavern’s historic charm and inviting ambiance make it a top choice for winter dining. Their George Washington Eggnog and Moscow Mule, enjoyed by the fireplace, offer a warm and cozy escape. Seasonal creations and classic pairings ensure an exceptional experience.
No matter your preference—bold and robust or sweet and comforting—the best winter cocktails in Annapolis are sure to elevate your winter evenings. Visit these top spots and raise a glass to the flavors of the season!