If you spend some time in or around Annapolis, Maryland, you may hear Annapolis humorously referred to as a “drinking town with a sailing problem.” There are certainly thousands of boats in the vicinity; the local marinas and mooring fields are almost always full. And as for the drinking, it’s also true that there are many great bars in Annapolis.
In fact, you probably can see a bar within a few feet of nearly any vantage point of Main Street, West Street, or 4th Street in Eastport. Since it’s such a historic and walkable city, and Ubers are readily available, it’s the kind of town that lends itself to walking around town and popping into a few bars and restaurants to get a feel for all the city has to offer. To help you explore the bar crawl way, we’ve created this guide to what we think are some of the top bars to visit in Annapolis.
Since we’ve kept a boat here for 8 years, and now live in the area, we’ve done our fair share of sailing and drinking in the area. We thought we’d share some of our favorite bars to visit with you. As always, this is our opinion as middle-aged folks who appreciate a nice cocktail, good service, good value, and atmosphere, whose tastes range from fun dive bars to fancy craft cocktails. Since bars in Maryland are required to serve food, most bars have at least some small plates and appetizers, while others we mentioned are full restaurants that happen to have an excellent bar scene as well. Here are some of our favorite bars in Annapolis, listed in no particular order!
As always, specials, offerings, menu items, and hours can change frequently at these establishments. It’s a good idea to confirm any important details before you go by calling or checking their website or social media pages.
Adams on Fourth
424 Fourth St, Annapolis, MD 21403 adamsgrilleannapolis.com
Adams’ is an Annapolis and Eastport institution, known for their ribs and smoked meats, and — like many on this list– is primarily a restaurant. However, the latest Adam’s location in Eastport is relatively new, and as such, has become one of our new favorite gathering spots.
Adam’s on Fourth is across the bridge from downtown Annapolis on 4th Street in Eastport and has a welcoming, open, and bright space. The bar is the main focal point framed by the open two-floor seating and first first-floor open gathering place. Communal tables, high tops, and porch seats that overlook the street make this a new, beautiful spot to grab a drink in Eastport.
It’s conveniently located near Boatyard, Forward, and Davis’s, making it an ideal spot for an Eastport bar crawl. We appreciate the nice selection of drinks like crushes and domestic bottles, the full bar, and the fact that you can enjoy the full menu at the bar. The service is top-notch – the bartenders are wonderful about remembering past patrons and treating everyone with warm and efficient service.
Davis’ Pub
400 Chester Ave, Annapolis, MD 21403 davispub.com
Davis’ Pub is an Annapolis and Eastport institution, and a night on the town in Eastport is hardly complete without a stop here. It’s a small, unassuming building with outdoor picnic tables for diners. Davis’ serves great food, and is an especially great spot to stop for dining with your dog!
Inside, there are a few coveted tables, and the elevated pub food served here is wonderful. The Super Salad, Reuben, chicken salad sandwich, Crabby Tots, and Monday night pot roast special are some of our favorite things to order.
However, after dinner and on most weekend evenings, Davis’ is primarily a gathering spot as the local bar. Davis’ can draw a crowd most days, and is elbow-to-elbow standing room only on the weekends or when there’s a big event in town.
In addition to having additional domestic drafts and local beers on tap, the bartenders can expertly and quickly create cocktail classics like Dark ‘N’ Stormies, Moscow Mules, and nearly any other drink you crave. While it’s a bit of a dive bar vibe, and there won’t be special garnishes or cocktails in coupe glasses, you will get a pint glass filled with an excellent drink and great service. You can’t really say you’ve gone on a bar tour of Annapolis unless Davis’ is one of your stops!
Boatyard Bar + Grill
400 Fourth St, Annapolis, MD 21403 boatyardbarandgrill.com
The Boatyard is another classic and must-visit bar when you’re in Annapolis. Like many of the places we’ve named here, Boatyard is primarily a restaurant that serves exceptional local seafood, sandwiches, salads, and entrees from its extensive menu.
However, the bar at Boatyard itself is a renowned gathering spot, hosting everyone from sailors after the Wednesday night races to celebrities. The decor in the Boatyard is like a beautifully arranged gallery featuring relics from the Chesapeake Bay and from popular ports around the world. The walls and nooks showcase a collection of trophies, signage from local marine businesses, photographs of famous vessels, and fine art with a maritime theme.
The architectural elements of shiplap and wood beams carry the boating aesthetic throughout. Despite being chock-full of interesting decor, the Boatyard feels clean, open, airy, and welcoming.
While you can have nearly any cocktail you desire, the boat drink and classic style cocktails like a Bloody Mary, Pimm’s Cup, a Dark and Stormy, Orange Crushes, and tropically inspired cocktails.
The bartenders at Boatyard have been there for years and treat newcomers and regulars with their good-natured and efficient service. Best of all, you can always enjoy any of the food from the extensive menu at the bar. Since our marina is just a half a block away, we’ve been known to eat breakfast, lunch, and dinner here in the same day!
The primary bar is located just inside the front entrance. To have a quieter time and to enjoy proximity to the oyster raw bar, the back bar is a fun, snug spot, especially if the main bar is too boisterous. It’s not always open, but when it is, it’s a hidden jewel in the spot that’s already a gem. Whether you want the freshest seafood or to celebrate a successful day on the water, Boatyard is one of Annapolis’ finest bars.
Parley Room
25 State Cir, Annapolis, MD 21401 parleyroom.com
If you’re seeking a well-made craft or classic cocktail, Parley Room is a must-visit spot for you. Not only will your cocktail be made with expert care and well-balanced ingredients that indicate true mixology, but your delicious drink is very likely to be served in an aesthetically pleasing coupe or glass, with a garnish that makes it a complete work of art.
The 1920 cocktail bar setting at the Parley Room is equally appealing. This prohibition-style meets the updated 1920s style is located in the historic Capital Hotel building in State Circle. The outside brick terrace is a beautiful contrast to the cozy, intimate style of the prohibition style bar, and makes for a great spot to enjoy people watching on this historic street, and offers a perfect view of the State House building.
As far as what to order, The Cafe Parley is their excellent take on the espresso martini. We’ve also never gone wrong with the OG or any of the mixed cocktails or daily special drinks. We’ve also attended some fun events here, like whisky pairings and charity events. The food here is exceptionally good, and like the cocktails, the presentation is always a work of art.
Carrol’s Creek Cafe
410 Severn Avenue, Annapolis, MD carrolscreek.com
Carrol’s Creek Cafe is one of the best seafood restaurants in town. It’s also one of the few restaurants in Annapolis with a waterfront view. Since our bar trips are frequently just the two of us, looking for a light dinner as well as a drink, Carrol’s Creek is one of our top destinations. The only drawback to the bar at Carrol’s Creek is that it’s tucked at the back of the restaurant and doesn’t really have a view of the water, except for perhaps a few glimpses from the bar table seating.
However, the excellent food, drinks, and exemplary service from the welcoming and attentive bartenders make up for the lack of a water view from the bar. Carrol’s often has a great selection of wines by the glass, local craft beers, as well as craft cocktails. We like their Chesapeake Bae cocktail as well as a gin and tonic made with a Scottish rhubarb gin. You also can’t go wrong with anything off the menu, like the Herb Encrusted Rockfish and starters like the Sea Scallops in phyllo dough.
Fox’s Den
179B Main St, Annapolis, MD 21401 foxsden.com
Fox’s Den made our list for one of our favorite places for pizza, and we feel we need to include it here as one of our favorite bars. In addition to the great wood-fired pizza, it has one of the best selections of craft beers on tap, from hard-to-find breweries we love like Dewey Beer, Troegs, and RAR. We also like their Sneaky Neighbor cocktail and their wine by the glass offerings. The bar itself is indeed den-like, making it a cozy spot on a fall day.
Pearl
26 Market Space, Annapolis, MD 21401 pearlannapolis.com
The Pearl actually offers two bar spaces, with vastly different atmospheres. Pearl is the downstairs bar and restaurant, and Ponche is the upstairs Tiki Bar. We visited Pearl primarily to experience the upstairs Tiki Bar. The upstairs space is full of the tiki decor, lighting, and the sort of Polynesian drinks you’d expect from your favorite Tiki Bar.
Even though the decor aims to transport you to an island lounge, it’s also blessed with a great view of downtown and Ego Alley from its second-floor perch. The drinks were classic tiki offerings like Mai Tais and rum-based fruit drinks. Drinks can run $14-17 dollars which is a little steep, especially since the serving we had was small and full of ice.
We had the Navy Grog and another cocktail that we forgot to write down. We also ordered the pizza, which was not a traditional pie, but rather a long flatbread-style pizza. Service upstairs wasn’t particularly warm and welcoming the day we visited, but we were happy with our drinks and the atmosphere.
Chart House Prime
300 Second St, Annapolis, MD 21403 charthouseprime.com
The Chart House Prime, like so many spots we’ve mentioned, is far more than a bar; it’s a fine dining restaurant worthy of special occasions.
However, the bar and happy hour at Chart House Prime is a particularly wonderful upscale spot to enjoy a drink and their fine service in their beautiful waterfront setting in Eastport. While the bar itself has more of an obstructed water view, the dining space within Chart House does overlook the water, and the whole interior space of Chart House Prime includes the bar is both expansive and chic with a huge bank of windows that look out on Annapolis Harbor and where the Severn meets Spa Creek.
We love going for the happy hour, where some of their best craft cocktails and filling apps are available at a discounted price. It’s a great way to sample just a little bit of the good food and service that Chart House Prime is known for. The bartenders at Chart House Prime have been there for years and are exceptionally skilled at high-end service and creating beautiful drinks. It’s a great upscale start to the evening to be a patron at their bar.
The Choptank
110 Compromise Street, Annapolis, MD 21401 thechoptankrestaurant.com/annapolis
For a city that is all about being on the water, there are sadly very few restaurants and bars in Annapolis that have a waterfront location and water views.
Choptank has had a Baltimore location for several years, but is a relatively new arrival to the Annapolis dining scene, and it boasts a few beautiful bar areas that are a wonderful spot to get a drink and enjoy a waterfront view. Located in the heart of downtown Annapolis right along the famed Ego Alley, their rooftop seats afford a beautiful location and an absolutely beautiful appointed and decorated space, which is why we wish we could rave about this spot a little more.
Unfortunately, the service is pretty uneven here, so our experiences have been good and bad. Once we waited for about 15 minutes to even be acknowledged at a mostly empty bar on a very slow Tuesday afternoon this past summer, and the bar staff was not attentive at all. On another visit, late one weekday evening, we had a wonderful bartender who explained the specialty cocktail ingredients and made apt suggestions. Sadly, we’ve heard that the service is an uneven experience at dinner as well. It’s a huge space, so it lacks that intimate atmosphere found in most Annapolis establishments and is owned by one of the restaurant groups that seems to be taking over many Annapolis restaurants and bars, much to the chagrin of locals like us who are eager to have Annapolis maintain some of its charm. Still, it’s a popular spot because of the unbeatable water location, wide selection of seafood, trendy drinks, and decor.
Federal House
24 Market Space Annapolis, MD 21401 federalhouse.com
Federal House Bar is located downtown, right in the heart of the action near Annapolis’ city dock, Market House, and Ego Alley. It’s located in a historic building and is a classic spot to visit during a bar crawl or just to pop in for a drink. Federal House offers one of the most impressive menus we’ve seen of the Maryland State drink – the Crush – offering everything from the classic orange crush to varieties of watermelon and mango.
If beer is more your thing, beer aficionados will appreciate the extensive beer list, which is full of some great local craft beer and IPAs that have been sourced from some of the most desirable breweries in the US.
It’s also a great spot to grab a bite to eat at the bar during happy hour. The crab dip is one of our favorite appetizers to have here. They also offer an outdoor seating area, which is a great way to enjoy the market house area of Annapolis.
Reynolds Tavern and 1747 Pub
7 Church Cir, Annapolis, MD 21401 reynoldstavern.org
Reynolds Inn, located right off of Church Circle, has a few beautiful spaces to enjoy a beverage. Reynolds Inn is home to the historic 1747 Pub, which served as the shoe shop of the original owner, William Reynolds, and has been a historic eating and drinking venue for years. Reynolds Inn also has rooms and a legendary high tea.
This small space is an unmistakable trip back to the 1700s. When you step inside, you can easily imagine historical figures and the past residents enjoying themselves here during the 1700s. There’s a small bar area right when you enter the bar from the side steps, as well as a cozy hearthside seating area, which is one of our favorite spots on a cold winter’s evening.
In the summer, we always enjoy the beer garden-style outdoor seating. The spacious patio is surrounded by beautiful plants and trees, creating a little historic garden oasis that’s just right for spending a relaxing summer afternoon sipping daytime cocktails and enjoying their delightful food offerings.
The outdoor area features many tables, including a small bar and seating around one of the huge trees in the space. Both the tavern and the outside garden are frequently home to a talented string of local musicians. This is one of the many must-visit historic pubs in Annapolis, and a great spot to enjoy the shade and some music on a summer’s day.
Stan and Joes
37 West St, Annapolis, MD 21401 stanandjoessaloon.com
Stan and Joe’s may be a little less upscale than some bars we’ve mentioned; it’s a little rough around the edges dive bar with windows plastered in beer and drink specials and other posted advertisements, but it’s renowned for great service and is a great happy hour or bar crawl location.
We love it for their live music and their 1/2 off beers and drinks during their 4-7 happy hour. It’s an amazing deal and a great opportunity to order a top-shelf drink at a discounted price. We’ve also heard that the meatloaf and other weekly dinner specials serve great comfort food. Live music and a patio make this a classic stop on any tour of Annapolis bars.
Harry Brownes
66 State Cir, Annapolis, MD 21401 harrybrownes.net
Harry Brownes is a fine dining establishment specializing in old-school steakhouse service, fine steaks, and seafood, as well as their tableside Caesar salad. Located on the beautiful State Circle, Harry Browne’s has been a fixture in the Annapolis dining scene for years.
While it’s primarily known for fine dining, upstairs is an inviting little bar known as Harry’s Bar with classic cocktails and bartenders who offer exemplary service and ice-cold martinis.
In addition to the bar at Harry’s, club chairs and couches are making upstairs at Harry Brownes a great little spot to start or end an evening out on the town.
Harold Black
236 Main St, Annapolis, MD 21401 haroldblack.com
Not to be confused with Harry Browne’s (which I do all the time!) Harold Black is one of the newer bars in the Annapolis bar scene. The idea behind Harold Black is actually an old concept. It’s a speakeasy bar found at the lower level of Acqua Al 2, an upscale Italian restaurant. However, unlike a true speakeasy, there’s no password needed here; you just need an awareness of where the entry door is.
Once inside, you’ll be in a cellar-style bar with moody dark lighting and a cozy setting with booths and bar seats. Cocktails are a house specialty, with the espresso martini, Blood and Sand, and the Hemingway Daiquiri being some of our favorites. At around $14-$16 per drink, they are on the pricey end, but there’s a happy hour with $10 cocktails with apps, and snacks.
It’s a fun novelty to be able to promise a night in a speakeasy as part of your bar hopping. It’s a fun place to feel like you’re entering a secret club and the perfect place to enjoy a nightcap after a meal at Acqua Al 2.
Galway Bay
63 Maryland Ave, Annapolis, MD 21401 galwaybaymd.com
A visit to Galway Bay, an Irish bar and pub, is truly like taking a little trip to Ireland. Located on Maryland Avenue – one of the sweetest streets in Annapolis – as soon as you step inside, you’ll feel transported to your “local” in Ireland. We visited a few pubs in Galway, Ireland, and can vouch for the fact that Galway Bay feels just like one of those pubs.
This is the place where you can enjoy a perfectly poured pint of Guinness or enjoy cocktails that feature Irish spirits, including whisky and gin. The food and happy hour offerings are wonderful and have something for everyone. Our usual order is the Queen Bee mule along with the curry fries, cabbage rolls, and meatballs. There’s also frequently a live band or local musician playing Irish songs, to add to the authentic atmosphere.
Seasalt
1 Park Pl #7, Annapolis, MD 21401 seasaltannapolis.com
If you’re looking for an oyster bar experience with craft cocktails, one of Annapolis’s newest restaurants and bars might be for you! Seasalt is on West Street near the Westin and Hilton Garden Inn, so it’s the perfect stop for some oysters and a cocktail if you’re staying in that area.
Seasalt has a huge bar as well as cozy restaurant seating areas, and the interior space has been completely renovated and very upscale atmosphere.
It’s the perfect stop for fresh seafood and a unique and sophisticated cocktail. We enjoyed the Gin Gin Buck at a discount during their Anchovy Hour happy hour.
Blackwall Hitch
400 6th St, Annapolis, MD 21403 blackwallhitchannapolis.com
If you’re looking for a roof deck to enjoy a few drinks and bites to eat, or some live music in Eastport, Blackwall Hitch is a great gathering spot. The lively and elegant bar can make any type of cocktail you’d like. In the summer, the rooftop deck and lounge seating are a great spot where you can enjoy drinks and apps with a view of town. In the winter, we love getting a spot in front of the fireplace and listening to local music.
Beacon Waterfront Galley and Bar
2020 Chesapeake Harbour Dr E, Annapolis, MD 21403 beaconwaterfront.com
Beacon is one of our favorite waterfront bar options. It’s outside of downtown Annapolis, and not accessible by walking from downtown, but it is just a short boat or car ride away in the Annapolis Roads area. For a waterfront town, bars directly on the water are pretty limited, but Beacon is one of the best waterfront options.
Not only is it a great dock and dine location, it has plenty of parking for those making the drive. Beacon is located in the gated area of the Chesapeake Harbor development. You’ll need to stop at the gate to get a pass to go into the restaurant.
While the inside bar offers a great view of the water in the fall and winter months, we particularly appreciate the long bar and outdoor seating area that is right on the water, where Beacon is one of the few waterfront spots with a mix of bar and outdoor seating, and plenty of room for a crowd.
They make excellent crushes and Dark and Stormies, and have some weekly specials like discounted crushes on Sunday Funday and Smashburger. They have also recently updated their menu with delicious small bites like the Deconstructed Smoked Salmon Arancini.
Dark Horse
985 Bay Ridge Rd, Annapolis, MD 21403 darkhorseannapolis.com
While Dark Horse may not be a destination bar, it is an institution. Dark Horse is our local neighborhood bar in the Annapolis Neck area.
If you’re looking for a spot away from the crowds of downtown, or you are looking for a find of dive bar meets sports bar atmosphere to grab a few rounds with friends and possibly make some new ones, this bar is a great stop. They have trivia and are a prime spot for watching football. They also frequently have local bands adding to the fun.
Rams Head Tavern
33 West Street, Annapolis, MD 21403 ramsheadtavern.com
Speaking of bands, Rams Head Tavern is our local music venue that brings in some amazing headliners. We’ve been lucky to see national acts like the English Beat and Mac McAnally there.
The bar at Rams Head Tavern is stocked with offerings from their own brewery, Fordham & Dominion, as well as delicious pub food. On Sundays, during brunch from 10 -2, they are known for their legendary Bloody Mary and Mimosa bar.
Rams Head also has other locations like Rams Head Roadhouse, which is right down the road near Crownsville, MD, where we enjoy their lobster special. We’ve also visited their location in Key West, which boasts an inviting outdoor seating area and an outside version of their Bloody Mary bar.
Dry 85
If you love good whisky and bourbon, Dry 85 is the spot for you! Dry 85 is another speakeasy-style bar that offers whisky flights, bourbons, and craft cocktails that feature some of the whiskies and bourbons, as well as other very inventive cocktail creations like the Brass Monkey and the Cereal Killer Old Fashioned.
This bar is full of atmosphere and a great spot to duck into when you’re heading up or down Main Street. It also offers a great (bacon-filled!) brunch.
Middleton Tavern
For history buffs wanting to add a stop to their bar crawl, Middleton Tavern is a historic tavern located right near Ego Alley and just down the street from the United States Naval Academy, and one of the oldest continuously operating taverns in the US. This historic watering hole was once frequented by George Washington, Thomas Jefferson, Benjamin Franklin, and many other notable past and present-day Maryland names of note. We like going to the bar there for their famous Shrimp or Oyster Shooters, which are served with their delicious cocktail sauce and a chaser of beer. We also appreciate that they offer Keno!
McGarvey’s
McGarvey’s is one of the spots we’ve visited more for their delicious club sandwich and their unforgettable open dining room that has a tree in the middle!
We’ve heard that McGarvey’s is the site of many a first meeting, first date, and engagement, and there are plaques around the bar from all the happy events that have occurred here. For nostalgia and an authentic Annapolis experience, add McGarvey’s to your list!
More Bars to Love
Remember how we said you might have different criteria for what makes the best bar? Truth be told, you can’t go wrong with really any of the restaurant bars and spots in Annapolis. Just like a rising tide lifts all boats, the consistent clientele mix of Annapolitians who enjoy a good drink has made every bar bring its best. Whether you’re visiting the city for fun, in town for one of the boat shows, or visiting your loved ones at St. John or the Naval Academy, there’s a bar to suit every group.
Again, this was written from and for the perspective of wanting atmosphere and good cocktails. For the younger crowd and the Naval Academy Midshipmen, you may find that bars like Acme, Dock Street, Armdillo, and O’Brien’s are the place to be!
More Eating and Drinking Ideas
We have more ideas for where to eat and drink, no matter where your travels take you! Pizza and drinking always go together, which is why we’ve created our guide to our favorite pizza places in Annapolis. If you’re heading south, you might like our thoughts on the best places to eat in St. Augustine, Florida, or the best happy hours in Marathon, Florida.
All opinions are our own. Images are original photographs by Currently Traveling editors and may not be reproduced without permission.
Shrimp and grits from St. Augustine Fish Camp
Fish dip appetizer 
The open-flame outdoor grill at Asado Life
The Asado Trio
Interior bar sand dining pace at Asado Life
Seared scallops and chow chow with red pepper gastrique
The Stuffed New York Strip from River & Fort
The Rooftop at River & Fort offers flatbreads and cocktails
Beet Salad with the Catch of the Day
Not Your Momma’s Meatloaf
Waffles with fruit 
Island-inspired cocktails are a specialty at The Beachcomber
The Painkiller at The Conch House is authentically and perfectly made
Tiki style outdoor seating huts at The Conch House
Shrimp and grits from The Conch House
Shrimp Anastasia seafood pasta
Interior space at The Ice Plant
The Ice Plant Truck
The Prohibition Style Atmosphere at the bar at Prohibition Kitchen
The Bootlegger Burger
The famous fried shrimp and sides at O’Steen’s
Pad Thai 
The Elton John roll, one of the chef’s specialty rolls at Andaman
Eggplant Parmigiana Pizza
The Sunset Salad
The Sunset Shrimp
The bar is now beautifully appointed with updated chic tropical decor. The cocktails are fantastic, and all of our favorites are on the daily happy hour which is $1.50 off signature drinks and $1.00 off beer, wine, and canned cocktails. We love the Painkiller, Rum Runner, Pina Colada, and the Strawberry Margarita. The tacos from the taco truck, aren’t a part of the happy hour, but grab a fish taco and then settle in for a few drinks during happy hour for a wonderful evening.
Our biggest reason to recommend the S. S. Wreck is the key lime pie! We think it’s the 
View of the RV sites and Cabins in the evening at Boothbay Craft Brewery & RV Park
The Watershed Tavern provides delicious farm-to-table food, craft cocktails, and stellar beers made on-site at Boothbay Craft Brewery
This area at Watershed Tavern hosts music and food from local farmers. We enjoyed fresh scallops and oysters from Brother Shucker here.
The Footbridge Across the harbor in Boothbay is one of the many historic and scenic attractions by the water in this quaint town
Kaler’s offered waterfront dining with a panoramic view of the harbor, excellent food, drinks, and welcoming service
No cooking and easy clean up is appreciated when you’re trying to eat lobsters in an RV. Pinkham’s Market will steam lobsters for you. We took them back to our campsite and ate them there!
Indian River Inlet Bridge in Rehoboth Beach Delaware
Walkway from the Campground to the Beach, Heading back to the Campground
Dunes and the Lovely Beach near Delaware Seashore State Park
Views of Matt’s Fish Camp Bethany Beach
Lunch at Dewey Beer Company and Sample Sizes of Secret Machine Fruited Sours