Whether you’re strolling downtown for Midnight Madness, shopping at the Annapolis Town Center, or simply leaning into the festive mood, Annapolis’ restaurants and bars go all-in for the holidays. If you’re out tackling holiday errands, strolling downtown for last-minute gifts, or simply trying to stay merry between stoplights and shopping bags, Annapolis has no shortage of places to grab a drink with a side of festive. From Irish egg nog traditions to cranberry-flavored drinks, these local spots deliver the seasonal spirits (and spirit) you need to fuel your December.
Cooper’s Hawk
If your errands take you to the Annapolis Town Center, Cooper’s Hawk delivers a full holiday experience; cocktails, wine, and gifting options all in one stop.
Cocktail highlights include:
- Cranberry Aperol Spritz — Red Sangria, Spiced Cranberry Syrup, Aperol, Prosecco
- Winter White Cooler — Grand Marnier, Winter White, Spiced Cranberries
And if you’re holiday shopping, don’t miss their December Wine of the Month or the Merry & Mulled Collection, a curated assortment of wine-centric gifts in deep reds, whites, metallics, and mulled-wine hues. Perfect for hosts, friends, or your own festive table.
Federal House Bar & Grille
Right off Market Space, Federal House keeps things classic and cozy with a lineup of new winter cocktails, including the popular Not Your Average Cup of Joe. It’s the perfect option for warming up between shops or enjoying by the fire.
Their Winter Warmers come garnished with an array of sweet treats. As always, Federal House brings together great drinks, great people, and that familiar holiday buzz.
Fox’s Den
Tucked on Main Street, Fox’s Den is exactly where you want to end up on a chilly evening. There’s dim lighting, exposed brick, candles, and all the cozy vibes.
Their winter drink list leans into seasonal craft brews, including:
- Downeast Cider House Winter Blend Cider
- Beer Farm BBF9 Cranberry Apple Sour Ale
- Beer Farm Mexican Hot Chocolate Cream Ale
- Atlas Silent Neighbor American Stout (Nitro)
If you love winter beers or just want something hearty and comforting, Fox’s Den has you covered.
Galway Bay
In Annapolis, holiday season doesn’t officially begin until Galway Bay’s Irish Egg Nog arrives. Their handcrafted liqueur, produced in Ireland, is blended in small batches and shipped to Galway Bay every holiday season.
To celebrate the season, Galway Bay rolls out a full Egg Nog Cocktail Menu, turning this iconic Irish import into a lineup of holiday sippers you won’t find anywhere else. Some of our favorites include the Espresso Nog ’Tini which is their signature Guinness Espresso Martini with a shot of their Egg Nog.
The Peanut Chocolate Cup which has Skrewball peanut butter whiskey, chocolate liqueur, and egg nog mixed together to create a boozy Reese’s cup on the rocks. If you’d like something warm, you can’t deny their Hot Chocolate Nog that has hot cocoa, chocolate liqueur, and egg nog topped with fresh cream.
Stop in for a cocktail, stay for the cozy pub glow, and don’t forget to ask about taking home a bottle (or two) of their famous nog.
Pearl
Yes, pink is absolutely a holiday color, and Pearl proves it with a chic, cheerful décor style that makes the whole restaurant sparkle this time of year.
Their big December draw? Holiday Movie Night, complete with half-off bottles of wine and their charcuterie boards. Perfect for a mom’s night out!
- Dec. 10: Love Actually
- Dec. 17: Elf
No tickets needed! Just walk in, sip something delicious, and enjoy your festive film of choice.
Rams Head Tavern
Whether you’re stopping mid-shopping or finishing the night with something sweet, Rams Head Tavern offers a rotating list of seasonal beers and cocktails. It’s the perfect spot to wander into off West Street and have a festive drink. The star this year? The Peppermint Patty, a minty dream that tastes like the holidays in a glass.
Red Red Jingle Bell Bar
For full-immersion Christmas cheer, look no further than Red Red Wine Bar, which transforms each year into the delightfully over-the-top Red Red Jingle Bell Bar. Think floor-to-ceiling décor, glowing lights, and holiday spirit in every corner.
The cocktails are just as spirited. Favorites this season include the Coco Cran RoseMerry Fizz, a bright and bubbly option; the Gingerbread Old Fashioned, which tastes like a Christmas by the fire; a classic Hot Spiced Mulled Wine that warms you from the inside out; and the Peppermint Espresso Martini, a holiday twist on one of their most popular cocktails.
This is Annapolis’ answer to having a holiday pop-up bar and we never miss a chance to visit.
From traditional Irish nog to peppermint cocktails, mulled wine, winter beers, and movie-night pairings, Annapolis’ restaurants take holiday cheer seriously. Whether you’re grabbing a drink after work or making a night of it with friends, there’s a spot—and a seasonal sip—waiting for you.
Here’s to a festive, flavorful holiday season in one of Maryland’s most charming towns. Cheers!
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