Happy TravellerAh, Annapolis! The enchanting capital of Maryland is more than just a picturesque harbor town; it is a treasure trove of American history waiting to be uncovered. As a self-proclaimed history buff, I can’t think of a better way to spend a weekend than wandering the streets where legends have walked, exploring colonial architecture, and indulging in stories that echo through time. If you’re eager to dive into the past while enjoying the present, let me guide you through a perfect weekend in this charming city.
Day 1: Arrival and Historic Charm
After settling into your cozy accommodations—consider the historic Governor Calvert Inn located right in the heart of downtown—you’ll want to start your journey with a stroll down Main Street. This vibrant thoroughfare is lined with colonial-era buildings, boutiques, and delightful cafes. Grab a cup of freshly brewed coffee at Langley’s and prepare to embrace the exploration ahead.
Explore the State House
No trip to Annapolis is complete without a visit to the Maryland State House. Established in 1779, it was here that George Washington famously resigned his commission as commander of the Continental Army. Imagine the weight of that moment as you step into the very room where it happened! Guided tours are available, and I highly recommend taking one to hear fascinating anecdotes from knowledgeable guides who bring history to life.
Walk the Historic District
Next, meander over to the Historic District. The narrow streets, lined with beautifully preserved 18th-century homes, are a testament to Annapolis’ storied past. Don’t miss St. Anne’s Church, where you can admire its stunning architecture and serene atmosphere. The churchyard is a peaceful place to sit and reflect on the countless souls who have walked these grounds before you.
Day 2: Maritime History and Culinary Delights
Start your second day with a hearty breakfast at Miss Shirley’s Cafe, where the crab cake benedict is a culinary delight that pays homage to the local seafood culture.
Visit the U.S. Naval Academy
After fueling up, make your way to the U.S. Naval Academy. This prestigious institution offers guided tours that delve into its rich history dating back to 1845. As you wander the grounds, don’t miss the beautiful Chapel with its stunning stained glass windows and the touching Naval Academy Museum that showcases artifacts from the naval history of the United States.
A Sail on the Chesapeake Bay
What better way to immerse yourself in the maritime legacy than by taking a sailing tour on the Chesapeake Bay? Several local companies offer afternoon sails, where you can soak in the stunning views and perhaps catch sight of some dolphins frolicking in the water. The history of the bay is rich, and it’s impossible not to feel connected to the past while on the water.
Evening Activities and Farewell
As your day winds down, treat yourself to dinner at O’Leary’s Seafood, where the fresh crab and Maryland-style seafood will leave you reminiscing about the flavors of the Chesapeake. If you’re up for it, enjoy a nightcap at The Federal House, a historic tavern that dates back to the 1700s, where you can sip a local craft beer while reminiscing about your adventures.
Before you depart, take a final stroll along the waterfront to watch the sunset over the harbor—a perfect closing to a weekend steeped in history. Annapolis is a city that invites you to connect with its past, and as you leave, you’ll carry a bit of its story with you.
So, whether you’re a seasoned history buff or someone simply seeking a weekend of charm and discovery, Annapolis has something special to offer. Pack your bags, and prepare to unlock the secrets of this historic jewel!
