It’s a story you’ll (hopefully) remember from high school history class. When George Washington took the oath of office in 1789, he did so in New York City, the first national capital of the United States under the Constitution. By 1790, however, the capital would be relocated to Philadelphia, where it would remain for the next decade while the new and lasting federal city was under construction in the District of Columbia.
What you may not remember is that under the Articles of Confederation—the precursor to the Constitution—Congress convened in five different “capital” cities between 1781 and 1788. Among them was the harbor city of Annapolis, the seat of American government when the Treaty of Paris was signed in 1783, ending the Revolutionary War. Later that year, George Washington would famously resign his commission as commander-in-chief of the Continental Army in Annapolis, intending (but failing) to retire quietly to Mount Vernon.
Today, Maryland’s capital is home to nearly 40,000 people, as well as the additional four million that visit its shores each year. And while Annapolis has lost much of its historic shipping and seafood industries to the nearby deepwater harbor of Baltimore, this bayside city remains one of the Chesapeake’s most charming destinations for recreational sailing.
A mere 30 miles from Washington, D.C., it’s also the perfect weekend destination when an extra day off just isn’t in the cards. So pack your bags—we’re setting sail for the next two days.
Severn Devils All Around You
The United States Naval Academy has been the heart of downtown Annapolis since the school was founded on ten acres of Fort Severn back in 1845. The campus has since gained 328 acres of land and countless notable graduates, including one president, two Nobel Prize winners, and 73 Medal of Honor awardees.
With a cup of local City Dock Coffee in hand, meet up with one of the guided walking tours that frequently depart from the visitor center. For the next hour and 15 minutes, you’ll enjoy a fascinating introduction to the life of a midshipman, from living in the largest dormitory in the world to concluding plebe year by scaling the lard-covered Herndon Monument (52 King George Street).
The Steak Pit
Maryland-style pit beef and turkey may not be the first dishes that come to mind when you think of Annapolitan cuisine—but they should be. Take a lunchtime detour a few miles south to Edgewater, where Bayside Bull BBQ is turning out some of the region’s best open pit top round beef and smoked turkey. It’s a no-frills, cash-only, seatless joint—but the sandwiches are piled high, the baked beans are perfectly sweet, and the staff is always as friendly as can be (108 Central Avenue West, Edgewater).
For many visitors, a trip to downtown Annapolis is confined to Main Street and its largely uninspired collection of tourist-oriented shops. But wise long weekenders will head a few blocks north to Maryland Avenue, a quiet home to the city’s most charming small businesses. From home décor and antiques to freshly-pulled pints of Guinness at Galway Bay Irish Pub, you’ll have plenty to keep you entertained for the next few hours. And you’ll be doing it all in the shadow of the State House, topped by the nation’s largest wooden dome constructed without nails (Maryland Avenue between State Circle and Prince George Street).
A Vin Down By The River
Even before the doors open at 5 p.m., you’ll find a crowd of hungry Annapolitans lined up outside VIN 909 Winecafé in Eastport. Opened in 2011 by manager-owner Alex Manfredonia and chef Justin Moore, this local favorite pays homage to the Mediterranean-inspired cuisine of California, tapping the resources of local organic food purveyors along the way. The brick oven pizzas are wonderfully fresh and inventive, while the hand-pulled mozzarella with heirloom tomatoes and balsamic “pearls” should not be ignored. And if it’s a beautiful evening, do yourself a favor and wait for a table on one of the lovely flower-lined patios (909 Bay Ridge Avenue).
I Am Serious, And Don’t Call Me Shirley
For nearly a decade, Miss Shirley’s Café has been treating its loyal patrons in Baltimore to decadent Southern-inspired cuisine with a Maryland twist. Crab cake and fried green tomato eggs benedict? Check. Benne seed chicken and waffles? Check. So imagine Annapolitans’ delight when Miss Shirley’s opened a local outpost in late 2011, bringing the memory of beloved Baltimore cook Shirley McDowell 30 miles south. While the menu offers countless (sometimes pricey) temptations, don’t pass up the sweet, berry-filled, and delightfully inexpensive homestyle pancakes (1 Park Place).
Sail Away, Sail Away, Sail Away
If you sailed into town, you already know how you’re spending the day. But boatless long weekenders fear not—there are still plenty of options to explore the Chesapeake Bay. Novices should consider a class at Annapolis Sailing School, a local institution that can teach you the ropes in several hours, or over the course of a few days (7001 Bembe Beach Road). But if you’re in the mood for some relaxation, let Captain Tony Ireland take the helm of Classic Sail Charters’ world-class yachts. Whether you opt for a morning, afternoon or sunset sail, Captain Tony will guide you and your companions on an unforgettable cruise in the nation’s largest estuary (7040 Bembe Beach Road).
Just don’t set sail without packing a picnic from Leeward Market, a local favorite nestled in the heart of Eastport. The staff is warm and welcoming, the ingredients are local, and the sandwiches simple and delicious (601 Second Street).
A Few Notes
For many visitors to Annapolis, the weekend just isn’t complete without a big, mallet-pounding meal of steamed Maryland blue crabs. If you insist, I completely understand. But be forewarned—in recent years, many of the city’s seafood joints have fallen into an unfortunate pattern of overpricing and underperforming.
Since 1974, Annapolitans have often brought their visitors to Cantler’s Riverside Inn, a local institution on Mill Creek that specializes in steamed hard shell crabs. While the crabs are still fresh and tasty in the summer, the rest of the fry-heavy menu falls woefully short (458 Forest Beach Road). In late 2012, however, The Point Crabhouse and Grill took over a pier on Mill Creek, and has earned early accolades for its simple, steamed Maryland seafood and fresh, varied menu (700 Mill Creek Road).
TITLE: The Maryland State House | SATURDAY: The dock of Annapolis; the Naval Academy Chapel; Bayside Bull BBQ; the State House, viewed from Main Street; Vin 909 Winecafé; pizza at Vin 909 Winecafé | SUNDAY: Blackberry pancakes at Miss Shirley’s Café; setting sail on the Chesapeake Bay.
I’m Maura O’Brien, a professional writer & editor, amateur photographer, and lifelong adventurer based in Portland, Oregon. The Long Weekender is my travel home—a blog that both documents my most memorable travel experiences and (hopefully) helps you make the most of your weekends. Looking for budget-friendly suggestions for where to eat, drink, and play during your next jaunt in the United States or abroad? You’ve come to the right place.
Tips? Comments? Feedback of any kind? Don’t hesitate to contact me at firstname.lastname@example.org.