top of page
  • Writer's pictureDeanna Sansbury

Out & About in Annapolis

Since we’ve lived in Annapolis for so long, I figured I’d do a post on some cool things/places we’ve learned along the way.  Checking out new destinations is always a cool experience, but it really helps to have a little insider knowledge of the place before you go.  I don’t know how many times we’ve been someplace, stuck walking the same few blocks usually “downtown” (aka tourist trap area), only to learn after we’ve left of the cool local neighborhoods where the locals hang out only a few blocks farther.  Annapolis is a great little town with so much more to offer just a short walk beyond the Main Street/Downtown area that is usually gridlocked with tourists. 

Ego Alley / Waterfront Area

Ego Alley is a small channel that cuts into downtown Annapolis (aka City Dock), which hosts an endless parade of boats driving down the channel, turning around and driving out. It’s the place to see and be seen – mostly for those with big boats to show off (hence the name Ego Alley).  Our first experience on the dinghy in Ego Alley left us with a slightly bruised ego, but thankfully we’ve gotten better since then.

Yup – this is it.  The famous Ego Alley.

Pussers Caribbean Grill – located on Ego Alley, and the only waterfront restaurant in Annapolis (aside from the Fleet Reserve and Annapolis Yacht Club, which are private clubs), Pusser’s is named after the famous BVI rum, which was recently acclaimed by Forbes Magazine to be one of the 10 best rums in the world.  It’s also the official Rum of the British Royal Navy, and has been for the past 300 years. In fact, those British seamen were probably in a Pusser’s haze back in 1774 when those crazy colonials up in Boston threw all of their tea into the harbor.  Whoops.   Definitely have the Painkiller – level 4 if you dare!  This place gets pretty packed in the summer, especially at night, where it turns into a party crowd. That building next door is a Marriott, in case you need a room because you were part of the aforementioned party crowd.

Annapolis Market House – right at the end of Ego Alley.  Can’t miss it.  This place is constantly changing vendors, so who knows what will actually be in there at any given time. Currently, there is a natural food grocery store, smoothie shop, sandwich shop, falafel shop and gelato shop. The only thing odd about this place is the hours – it doesn’t open until 11:00 each morning, and shuts down at 7:00, which is a late open and an early close if you ask me, especially in the summer time when tourist crowds start early and end late.

Dock Street  / Armadillos / McGarveys Saloon / Federal House – these are all lumped together because they’re all basically the same type of bar.  Casual environment, great Happy Hour Specials, ok pub food, packed full of twentysomethings after dark on the weekends.  Go here during the day or weeknights if you want to avoid the club scene.  Bonus – McGarveys has a fantastic happy hour from 4-7 Mon-Fri.

Middleton Tavern – Established in 1750, this place claims to be the oldest bar in MD, and supposedly the preferred hangout for members of the Continental Congress back in the day.  We really like the bar at this place.  They have a great raw bar and offer unbeatable Happy Hour specials on steamed clams/oysters/shrimp.

Factor’s Row – This is a pretty new spot (within the past year), with a cool farm to table concept and a fresh, modern interior.  We’ve been here a few times and before and have been really happy every time.  It’s sort of a breath of fresh air in a space crowded with old historic buildings and seafood specials.

Sophie’s Crepes – great grab & go place right next to Ego Alley.  Choose from a huge selection of Savory or Sweet (or make your own), get it to go and eat it while walking the Naval Academy, which is right next door.

The Big Cheese / Sammy’s Deli – another great grab & go place with homemade subs and a gourmet meat & cheese selection.

US Naval Academy – Definitely worth the visit, if only for a walk thru the gorgeous grounds and historic buildings dating back to the 1700’s.  Check out the historic Chapel at the center of the Yard – and its landmark dome – which is built over the crypt of John Paul Jones, regarded by many as the Father of the US Navy.  Stop by the bookstore on your way out for some great souvenirs.  We have a USNA sweatshirt blanket that has been a staple on cold nights for the past decade.  Don’t forget your ID – you won’t get thru the security checkpoints without it.

Watermark Cruises / Walking tours – if tours are your thing, check out the water cruises and walking tours by Watermark.  They have a fleet of large yachts that will take you out for a few hours for a guided tour of Annapolis by water.  They have an old riverboat called the Harbour Queen that’s my personal favorite.  The walking tours include tour guides dressed in colonial character.  We did a walking ghost tour once and I’ll admit, it was really fun and the stories were very interesting.  I would definitely recommend it if you want to see the city by foot and are interested in the historic aspect.

Main Street / Downtown

Here’s where most of your retail shops are, ranging from the kitschy novelty shops selling Annapolis T-shirts (my personal favorite is one describing Annapolis as ‘a small drinking town with a sailing problem’), small fashion and home decor boutiques. Of course there are plenty of sailing themes stores like Helly Hansen (the next closest one is in Rhode Island, BTW) and a neat boutique store called Re-Sail, which sell accessories made from actual boat sails.  There’s also a CVS that has a pretty well stocked pantry section if you’re looking for some staples on the fly.  It’s all pretty touristy, but once you get to the top of Main Street, the view over looking the flag lined street and the Annapolis Harbor is totally worth it.

A few good places to eat:

Red Red Wine Bar – about halfway up main street on the left is RRWB, an anti-wine bar, designed for those of us who aren’t wine snobs.  This place has a laid back vibe, good food, and of course, a rockin wine list that features some serious wines in a lighthearted way (try the ‘Cab-bey Road’ flight of Cabernet Sauvignon or the ‘That Was a Crazy Game of Pinot’ flight of – you guessed it – Pinot Noir).  They have a sister bar – Dry 85 – that is a modern rum bar modeled after a Prohibition-era speak easy.  We don’t think it’s as good as RRWB, but if spirits are more your thing, it may be more up your alley.

Joss – hands down THE BEST sushi bar in Annapolis.  It’s not the fanciest of places, but the sushi here is freaking amazing.  This place is always packed, and the seating is super tight (like 12″ from the next table over), but the food is sooooo worth it. Also about halfway up Main Street, on the left.

Chick & Ruth’s Delly – an Annapolis staple.  This place is just as much a treat to the eyes as it is to the taste buds, with news clippings and photos taking up nearly every inch of wall space inside.  The food is fresh and plentiful – with the menu boasting FOUR Colossal Food Challenges, one of which was featured on Man vs Food  on the Travel Channel.  It actually makes my stomach turn just thinking about finishing a 3lb cheeseburger followed by a 6lb milkshake, but hey, whatever floats your boat, right?

Buddy’s Crab House – total tourist destination, where the view is great but the food is just OK.  If you want good seafood, head across the Eastport bridge to some great spots like the Chart House or Carol’s Creek.  I hear the crabs are pretty good, but we’ve never had them ourselves.

Church Circle / State Circle

Church Circle is located at the top of Main Street, and is the hub to which all of the main streets of Annapolis spoke from.  Here you’ll find St. Anne’s Church, originally built in the early 1700’s.  It was demolished and rebuilt in the early 1800’s, then demolished yet again and – you guessed it – rebuilt for a third time in the early 1900’s.  Guess they found a design they liked because the third and final version is what stands there today.  It’s a neat place to explore if you’re into the whole history thing – the church and it’s grounds are open to the public.

Over on neighboring State Circle, you’ll find the seat of the MD state government – the State House, Governor’s House and State Assembly.  All of these are rich in state history, and, if you don’t mind hanging out with a bunch of rambunctious grade schoolers on school field trips, available for tours as well.

Another cool place to check out is the William Paca House and Gardens.  This is a beautifully restored 18th century mansion, owned by William Paca, one of the four signers of the Declaration of Independence from MD.  Unfortunately you DO have to purchase a ticket for a tour, which we never have, but I’ve heard that the place is super haunted and a lot of crazy stuff went on in there. Friends of ours had their wedding reception in the gardens, which are pretty impressive, especially since this is nestled in the heart of downtown. How cool would it be to play a game of croquet or bocce on this lawn?

West Street / Uptown

Ram’s Head Tavern – a little pub with a great outdoor seating section around back that’s nice and private with plenty of heaters for those chilly spring/fall nights.  They also brew their own beer, and have a pretty impressive menu of beers on tap. Check out the bar in the stone cellar basement for some real historic charm.  Take a peak behind the bar and you’ll see a small wooden post protruding from the ceiling.  Supposedly the place used to be a brothel back in the day and during a particularly heated session, the floor collapsed and a bed post impaled, Amy, the hardest working girl there, killing her instantly.  Rumor has it that she still haunts the place and prefers to hang around the gentlemen, possibly looking for business even in the afterlife.

Ram’s Head On Stage – a super small music venue that attracts some pretty cool acts as they pass thru Annapolis.  The worst seat in the house is still better than the best seat you’d find at other venues.  Definitely worth checking out their schedule if you’ll be in town for a few nights.  The intimacy of seeing artists that up close and personal is guaranteed to be a great performance, no matter who’s on stage.

El Toro Bravo – great authentic Mexican restaurant.  It’s usually packed, but worth the wait.

Tsumani – a modern fusion sushi place, with a sexy and intimate vibe.  Great for a date night, or oggling the hipsters who seem to call the bar in this place home.

Metropolitan Kitchen & Lounge – another great farm to table place with an ever changing menu that features stuff from the garden they grow out back.  Plus they have the only rooftop bar in Annapolis, which is gets pretty sexy (the space and the people) after sundown.


Eastport is located just across the Spa Creek bridge, but it feels like an entirely different city.  It’s sort of like the anti-Annapolis, with a much more laid back (and slightly less pretentious) vibe.  In fact, the residents of Eastport (or Eastportaricans as they call themselves) value their uniqueness so much that they actually annexed from Annapolis proper in 1998 and formed the Maritime Republic of Eastport.  Trust me on this, Eastport is where the true locals hang out.

Carol’s Creek Cafe – fine dining on the waterfront overlooking the Annapolis Harbor.  If you choose to dine in the actual dining room, request a Caesar salad – made table side from scratch, it’s like a culinary orgasm in your mouth.  True story.  They also have an amazing Happy Hour in the bar area, with half price apps – and goooood apps too (no chicken wings on this menu!).

Chart House – normally I wouldn’t recommend chain restaurants like this, but the view overlooking the Annapolis Harbor is seriously spectacular.  Great food, awesome wine selection.

Lewnes’ Steakhouse – Founded in 1921, it’s possibly the oldest true steakhouse in Annapolis.  The inside is small and cozy, although a bit stuffy for our liking.  You can’t beat the steak though…. the melt in your mouth because it’s been broiled at 500 degrees in a pan of butter kind of steak.  Ah-mazing.

The Boat Yard Bar & Grill – a true sailor/local joint, with walls packed full of clippings of local sailors and fishermen from the Chesapeake region.  It’s been dubbed the ‘Nautical Cheers’, a nickname that it definitely lives up to. In our opinion, THE BEST CRABCAKES in Annapolis.

Davis’s Pub – possibly the best hole in the wall pub in Annapolis.  It’s where sailors exchange stories about maritime adventures hunched over a dark & stormy.  Ever since it weas featured on Diners, Drive Ins & Dives on the Food Network Channel, it’s been packed with authentic old salts and wannabe sailors alike. There’s even a dinghy dock where you can lock up, have a beer and walk across the bridge to Annapolis (come in via Back Creek, just past Horn Point Marina on the right).  Best place ever…. seriously try their crab pretzel.  Mmmmmm.

So there’s a snapshot of some of our favorite places in Annapolis.  We’d love to hear comments from anyone who’s visited or lived here on anything I’m missing?  Totally NOT agree with me on some places?  Have any other tidbits to out of towners to share? We’d love to hear your thoughts!

7 views0 comments

Recent Posts

See All


bottom of page