It’s time to trade orange crushes for pours that taste like autumn in a pint glass! We’re taking you on a fall-flavored pub crawl through the streets of Annapolis, where seasonal sips, cozy vibes and hometown charm are on tap.
Local favorites are bringing the flavor with pumpkin-spiced cocktails, espresso martinis, and Oktoberfest lagers that make you want to cheers with the stranger next to you. Whether you’re craving a pumpkin porter, a crisp apple martini, or a maple-kissed cider, there’s something worth raising a glass to this season (and maybe a crab dip pretzel to match).
So grab your friends and follow along as we share some of our favorite Annapolis spots for fall-inspired brews, cocktails, and bites. Cheers to sweater weather!
Chessie’s Wharf
Our first stop takes us to West Annapolis and a cozy local favorite, Chessie’s Wharf, where spooky season has officially checked in! Kick off your pub crawl with Jackson’s Harvest, their pumpkin beer that’s perfect for fall. Ready for round two? Sip on their Seasonal Vibes cocktail, a festive mix of Jim Beam Bourbon, Evan Williams Spiced, cinnamon simple syrup, apple cider and champagne.
Pairs well with: The Chessie Burger, grilled to perfection, and their infamous drunken tots. Because nothing says spooky season quite like carbs, cheese and a good drink!
Photo provided by Chessie’s Wharf.
Rams Head Tavern
Stop number two takes us to West Street, where Rams Head Tavern has been a downtown Annapolis staple for years. With a rotating lineup of seasonal drafts, including Sam Adams seasonal favorites and local brews, there’s always something new to sip. But our pick for fall? Their cocktail of the month, the pumpkin spice espresso martini, available for just $9 all day, every day!
Pairs well with: The Annapoli-taco, a deliciously loaded combination of crab dip, fried chicken, iceberg lettuce, cheddar jack cheese, pico de gallo and Old Bay aioli, all tucked into a flour tortilla with a crunchy taco shell. Because why choose between Maryland seafood and tacos when you can have both?
Photo provided by Rams Head Tavern.
Dry 85
Next up, we’re heading to Main Street to hang with our friends at Dry 85, where the fall cocktail lineup is giving us plenty of reasons to stay for another round! We’ve got three drinks on our must-try list. Red Smoke brings a smoky twist with tequila, Banhez mezcal, cranberry, fresh lime juice and agave. For something that screams fall, try Last Gourd, made with rum, house-made pumpkin cordial, fresh lemon juice and Licor 43. Or sip on The Fallen Apple, a refreshing mix of Ford’s gin, house-made apple cider cordial and fresh lime juice, topped with apple cinnamon foam.
Pairs well with: The Warm Skirt Steak and Quinoa Salad, featuring house-made fried goat cheese croutons, macerated grape tomatoes and organic mixed greens tossed in a roasted shallot vinaigrette. Because we should probably eat something between cocktails, right?
Fox’s Den
We’re staying on Main Street for our next stop, but heading underground to Fox’s Den! This cozy downtown favorite is serving up plenty of fall flavors, including New Trail Werewolf Pumpkin Stout, Downeast Ciderhouse Pumpkin Cider, and South County FestiFall Oktoberfest Märzen Lager. More of a cocktail person? Try their Maple Old Fashioned, made with Green River bourbon, maple syrup, peach and orange bitters, and garnished with an orange and cherry. It’s basically sweater weather in a glass!
Pairs well with: The Butternut Squash Soup, made with brick-oven-roasted squash, saffron oil, pumpkin-spiced crema and micro arugula. A cozy bowl of fall goodness to go with your seasonal sips!
Forward Brewing
We’re crossing the bridge into Eastport for the final stop on our fall-flavored pub crawl! Forward Brewing may be small in size, but it’s big on creativity and seasonal sips. Wind down with their Oktoberfest, a crisp, slightly toasty Märzen-style lager brewed with Munich and Vienna malts and Saphir hops. Or satisfy your sweet tooth with Mast Landing’s Gunner’s Daughter, a rich milk stout with notes of peanut butter, coffee, milk chocolate, roasted malt and vanilla. Talk about dessert in a glass!
Pairs well with: Two soft pretzels topped with Maldon salt and served with beer mustard. Because after a pub crawl through Annapolis, a little salty, carb-loaded goodness is exactly what we need to soak up all those fall flavors!
From West Annapolis to Eastport and everywhere in between, this fall brew tour covers every corner of the city we love. So grab your sweater, text your crew, and get ready to sip your way through spooky season.
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