Out on the Town | Travel

How To Spend A Perfect Weekend in Annapolis, Maryland

Maryland’s quaint waterfront capital delivers historic charm, delicious local food and an enticing array of short adventures and side trips to satisfy a wide range of visitors


It was the view that hooked me right away. Looking out from my hotel room’s balcony at the docks, the boats and the expanse of Chesapeake Bay before me, I knew I’d found a special place, and not just the balcony (which I’d enjoy both later that evening and for a glorious sunrise the following morning). I was keen to get out to explore the waterfront and the historic districts of this refreshingly small and walkable capital city.

While Annapolis may be well-known to day-trippers from nearby Baltimore and Washington, D.C. (both around 50 km away) it remains well off the radar for most of us in Canada and North East US.  However, it’s charming enough to warrant its own weekend trip, or at least an overnight while visiting the U.S. capital or another highlight of the region. Here are some ideas for your visit.

How to get to Annapolis and where to stay

While we dream about sailing or cruising into town on a luxury yacht (you can do that) the average Canadian visitor will either drive or fly. It’s a manageable and scenic eight hour drive from Toronto and nine hours from Montreal. There are many direct flights into Baltimore-Washington International airport about 40 km from Annapolis. A car rental or paid shuttle service will get you to Annapolis.

As I’ve already mentioned it, I’d highly recommended trying to get a room with a balcony facing the water at the Annapolis Waterfront Hotel. Weather depending, aim to rise with the sun. The balconies face east so you can sit out and take in the fresh morning air, the waters of the Bay smooth as glass, and the warmth and colours of the sunrise.

Annapolis Waterfront Hotel
The view from the balcony at the Annapolis Waterfront Hotel

There is a larger, slightly more upscale Westin Annapolis about a mile inland from the harbour, but it doesn’t enjoy the harbour views and proximity. There is also a selection of bed & breakfast accommodations scattered throughout town.

Get out on the Bay

At some point you really need to get out onto the water. Located right below our balcony, and right out the back of hotel was the mooring for Annapolis Sailing Cruises, a Annapolis experience staple, featuring their two wooden, 74 foot schooners, the Woodwind and the Woodwind II. The ships are beautiful, in immaculate condition and crewed by friendly professionals, happy to get you involved in the craft of sailing. Quick fact, Annapolis is known as “America’s Sailing Capital.”

annapolis sailing cruises woodwind schooner
annapolis sailing cruises woodwind schooner Captain Taylor Newland
Sailor for a day on the good schooner Woodwind

One of their ships had a starring role in the movie, The Wedding Crashers, and you should probably watch a clip of that on YouTube ahead of time just for fun. The schooner cruise is a fantastic way to spend a couple of hours, enjoying a couple drinks and a picnic on the waves while taking in the views of the harbour, the Bay, the coastline and a one-of-a-kind historic lighthouse, the Thomas Point Shoal Light.

Thomas Point Shoal Light. Lighthouse
Our closeup view of the iconic Thomas Point Shoal Light

Explore the shops and cafés around the harbour and along Main Street, day or night

Shopper or not, you’ll be charmed by the 18th century architecture, red brick roads and sidewalks, and a wide array of boutiques, art galleries, cafés and restaurants. The backdrop of the Annapolis harbour and its sailing ships makes for a postcard stroll while browsing for gifts or enjoying a coffee on an outdoor patio.

With a population of barely 40,000, Annapolis hosts more 18th century buildings than any other American city. The waterfront area is officially designated as a National Historic Landmark as well as a National Historic Treasure.

main street annapolis
The red bricked Main Street in downtown Annapolis

Tour the US Naval Academy

To some, Annapolis may be best known as the home of the United States Naval Academy with around 4,400 “midshipmen” studying and training here at any given time. Its counterpart for the Army is at Westpoint and the Air Force (think Top Gun) is Colorado Springs.

You can arrange a guided walking tour of the Academy, which was founded in 1845 at the site of an old fort on the water. The tours are usually conducted by a local with a keen love for the history, trivia and stories of the Academy and its notable buildings and training grounds. Bring your passport, you’ll need it to get past the guards into the grounds.

U.S. Naval Academy Annapolis Gate Ex Scientia Tridens
One of the main gates to enter the U.S. Naval Academy with the Navy motto “Ex scientia, tridens”

U.S Naval Academy Annapolis

Football fans will all be aware of the Army-Navy rivalry, the most famous, longest running televised (since 1945) annual match-up. And while that particular game is usually played in Philadelphia, the Navy football team trains and plays its six home games in Annapolis. Definitely a unique sports experience worth catching if the timing is right, and this past season saw a particularly strong Navy team go on to win all six of their home games in front of appreciative fans.

Explore the past

Annapolis, and particularly its historic district which begins down by the harbour and spans 45 blocks, makes for a great walking town, and especially for history buffs.  You can either read up on the history and visit key spots yourself or arrange for a guided tour. A check-in at the Annapolis Visitor Centre (45 West Street) is a great idea, staff there can help you with a map and an itinerary.

Annapolis was settled by Puritans who arrived in 1649 and called it Providence. It was eventually made the state capital and renamed in 1695 for the soon-to-be Queen Anne (who was portrayed by Olivia Colman in The Favourite recently winning a best actress Oscar). Annapolis served as the new nation’s capital city after the War of Independence, and its capitol building hosted the early American governments. That capitol building still serves as the Maryland state capitol building and makes for a fine vista (and photograph) perched up on its hill.

State Capitol Building Annapolis
The upper domed levels of the Maryland state capitol building can be glimpsed from most parts of Annapolis

Visit a local winery

One of several possible side trips, we’d recommend getting a little rustic over at Great Frogs Winery located just on the edge of town. It’s a nice change of scenery and artisanal food and wine pair perfectly with eachother and the setting. Winery visits and tastings are on Saturdays only and are by reservation only, so book this early when planning your trip. Sit down to sample several wine varieties, walk through the vineyards with a glass in your hand, or chat with the relatively young owners Andrea and Nathanel O’Shea about the joys of running a small winery.

great frogs winery annapolis

great frogs winery annapolis cold-blooded maryland
Trying the Great Frogs Cold Blooded reserve red, one of many French styles on offer

Where to eat in Annapolis

Annapolis offers up a very nice selection of a restaurants from classic pub fare to upscale chic. Being on the Chesapeake Bay, seafood should be your go-to cuisine as much as possible with Maryland Blue Crabs, rockfish and local oysters, “the holy trinity of Maryland seafood”, prepared in numerous delicious ways. Tip: try at least one crab cake everywhere you go, it’s fun to compare. Keep in mind the iconic Maryland foodie experience, eating delightfully messy steamed, freshly caught Blue Crab is really only available in the summer, so crab connoisseurs should aim to visit in June, July or August.

Carrol Creek Cafe Annapolis
A look at Carrol’s Creek Cafe, and the food matches the view, excellent

For an upscale seafood experience, we recommend Carrol’s Creek Cafe which is just a short stroll from the Annapolis Waterfront Hotel and provides nice views of the harbour and sunsets. They serve a great lunch and brunch but we’d save this one for an evening meal, ideally your special Saturday meal if you’re staying the weekend.  We stuck with the seafood offerings, and were fans of it all, particularly the cream of crab soup, the baked oysters and the nicely presented scallop dish. The restaurant has a strict no-nut policy, referring of course to its recipes not its guests.

Make sure you do not miss the Galway Bay Irish Pub, with it’s newly renovated dining room and even more impressively updated Irish whiskey collection, now featuring over 80 different Irish Whiskeys, not to mention all the other spirits and ales they serve. A great place for lunch as well, be it oysters, fish and chips or shepherd’s pie.

Galway Irish Pub
Galway Irish Pub’s award winning collection of Irish Whiskey

For a completely decadent breakfast or brunch experience that you’ll be thinking about for years, try the Iron Rooster, which is right down by the harbor. The menu is has many highlights but do your best to try their Waffles and Chicken, and (trademarked!) Roostart, essentially a extra large, no-holds-barred pop tart like you’ve never seen or tasted before (and instagrammable as well)! Warning, portions are very large, so count on sharing and taking leftovers to go. Oh, and did we mention bacon-in-jar, you get one free if you mention Iron Rooster on social media.

Iron Rooster roostart, bacon in a jar
The best chicken waffles were the best we’d ever had, one of several must try menu items at the Iron Rooster
Iron Rooster Waffles & Chicken
The Roostart paired nicely with the bacon in a jar. Calorie-counters save this combo for your cheat day.

There are many other dining and nightlife options, and the whole town is small enough to walk around and discover a couple of your own. Some establishments are over 200 years old, and some may be newly opened.

One last look at the fine view from my hotel balcony!

Whether it’s a targeted Annapolis-only visit or a wider tour of the Chesapeake Bay region, you’ll enjoy your visit to Maryland’s capital. You’ll be inspired by the seafood, the drink and waterfront’s charm and and the town’s friendly people. Odds are you’ll long to come back, and share your find with others.

Plan early for your summer visits, and for more trip planning advice check out VisitAnnapolis.org,

Even More Stories You May Like (courtesy of Google)

Comments are closed.