Annapolis, Maryland, may be best known today as the home of the U.S. Naval Academy, but its roots run much deeper, and as I discovered during my visit, historic highlights of Annapolis are everywhere you look. As one of America’s oldest cities, it played a major role during the colonial period and the early years of U.S. independence. In fact, for a brief moment after the Revolutionary War, it even served as the nation’s capital. Walk a few blocks through the Historic District and you’ll still find colonial-era buildings not only standing, but bustling with life.
Of course, that’s only a fraction of what Annapolis has to offer history-wise. In this article, I’ll take you along on a US travel journey through this marvelous city, covering major landmarks and cultural touchpoints, as well as share a few helpful tips I picked up for anyone planning their own visit.
The Brief History of Annapolis
Founded in 1649, Annapolis became Maryland’s capital in 1694. Its spot along the Chesapeake Bay helped it thrive as a port city, especially during colonial times. By the 18th century, it was a meeting point for ideas, trade, and early American culture.
One of the most powerful moments in U.S. history happened here in 1783, when the Continental Congress met in Annapolis and George Washington resigned as commander-in-chief of the Continental Army. I stood in that very chamber, imagining the weight of that silence as Washington handed over his power. It’s often seen as a defining act of democracy, one that marked the shift toward civilian leadership.
You can still feel the echoes of that past as you explore the city. The streets follow the same 17th-century layout, and many homes, churches, chapels, and government buildings from the 1700s are not only standing but still in daily use. I kept finding myself drawn to the doorways, some crooked with age, others gleaming with fresh paint, but each holding centuries of stories.
Historic Highlights of Annapolis
Many of the city’s key historic sites are within walking distance of each other. I spent an afternoon wandering with no real agenda, just curiosity, and was amazed at how much history I stumbled into. From colonial homes and churches to taverns that once hosted presidents, these places tell the layered story of early America. Whether you’re a history nerd like me or simply looking to spend a fun weekend in Annapolis, these are some spots you won’t want to miss.
Maryland State House
The Maryland State House, built in 1772, is the oldest state capitol still used for legislative sessions. It’s also the only one that once served as the U.S. Capitol. From November 1783 to August 1784, the Continental Congress met here, most famously when George Washington resigned his military commission, showing the importance of civilian control over the military.
Walking through its halls, I was struck by how well-preserved everything felt. The restored legislative chambers, the exhibits on Maryland’s political past, and the period furnishings all offer a vivid picture of 18th-century life.
William Paca House & Garden
This Georgian-style mansion belonged to William Paca, a Maryland signer of the Declaration of Independence. The moment I stepped into its grand entrance, I felt like I’d traveled back in time. Today, it’s a National Historic Landmark, carefully restored to reflect the 18th-century details of Paca’s life and times.
The guided tour shed light on both his political achievements and his private world. But it was the walled garden that stayed with me most, a peaceful two-acre space filled with heirloom plants, buzzing bees, and the faint scent of lavender in the air. It’s one of the best examples of Annapolis’s commitment to preservation.
Middleton Tavern & Reynolds Tavern
Dining in Annapolis means eating where history happened. Built in the 1740s, Middleton Tavern once welcomed guests like George Washington and Thomas Jefferson. Sitting there with a plate of crab cakes, I couldn’t help but picture the conversations that might’ve taken place at the same tables centuries ago.
Just a few blocks away, Reynolds Tavern (dating back to 1747) is equally charming. Today, it functions as a tea room, pub, and inn, with much of the interior retaining its original charm.
St. Anne’s Church
At the heart of Church Circle stands St. Anne’s Church, founded in 1692 and rebuilt in the 1800s after a fire. It’s still an active congregation, and when I visited, a quiet service had just ended. The scent of old wood mixed with candle wax filled the space, and sunlight filtered through the stained-glass windows.
The church’s history is tied closely to Annapolis’s own. Namely, several notable Marylanders are buried on the grounds, and inside, you’ll find symbols of the city’s spiritual and civic evolution.
Historic Downtown & Cobblestone Streets
Sometimes the best way to take in a place is just to walk. That’s especially true in Annapolis. As I wandered the Historic District, I found myself pausing to admire the worn bricks of centuries-old row houses, the colonial storefronts still welcoming customers, and the tree-lined sidewalks buzzing with local life.
There are plaques and signs along many of the buildings, making it easy to turn a casual walk into a self-guided history tour. But what really brought the past to life were the locals, many of whom seemed happy to share stories or directions with a smile.
The Legacy of the U.S. Naval Academy
Of course, no visit to Annapolis would be complete without exploring the U.S. Naval Academy. Founded in 1845, the Academy is located right along the Severn River, just steps from downtown.
The campus, often referred to as “the Yard,” is home to several landmarks worth seeing. Bancroft Hall, the largest dormitory in the United States, is impressive in size and architecture. The Naval Academy Chapel, with its massive dome, is another standout. Below it lies the crypt of John Paul Jones, the Revolutionary War naval hero often called the “father of the U.S. Navy.”
The U.S. Naval Academy Museum, tucked inside Preble Hall, surprised me with how immersive it was. Ship models, naval artifacts, and stories of both war and leadership made me reflect on how deeply the sea has shaped American history.
Visitors can enter the Academy grounds with a valid ID, but I recommend taking a guided tour. Ours was led by a retired officer whose pride in the institution was contagious, and who peppered his tour with anecdotes that made the buildings feel alive.
Practical Tips for Visiting Annapolis
If the historic highlights of Annapolis have you itching to go, here are a few tips from my own experience:
Best Time to Visit
Spring (April-June) and fall (September-November) are ideal. The weather is mild, and the city hosts several history-themed events, including Maryland Day in March and Naval Academy Commissioning Week in May.
Getting Around
Annapolis is very walkable, especially within the Historic District and around the Naval Academy. Parking downtown can be limited, though, so consider using public garages or the Annapolis Circulator Trolley, which is a convenient and inexpensive way to get around.
Tours and Passes
To go deeper, try a themed walking tour. There are ones focused on colonial history, haunted sites, or waterfront views. The Historic Annapolis Pass is also a good deal if you plan to visit multiple museums and landmarks.
Where to Stay
For a more immersive trip, I recommend booking a room at one of the city’s historic inns or B&Bs. Mine was the Maryland Inn, and it balanced 18th-century character with modern comfort beautifully. Plus, being within walking distance of everything made the experience even better.
Local Dining
Food-wise, you can’t leave without trying a proper Maryland crab cake. I had mine at Middleton Tavern with a side of oyster stew, and it was every bit as rich and comforting as the surroundings. Still, no matter which local spot you choose, chances are you’ll enjoy something memorable, as many restaurants here embrace colonial-inspired dishes.
Why Annapolis Is Worth a Visit
Annapolis is one of those rare places where history weaves naturally into everyday life, and that’s especially clear in the many historic highlights of Annapolis. If you’re searching for a destination that’s both charming and culturally rich, this one delivers. Whether you stay for a weekend or linger longer, the stories, architecture, and atmosphere make this colonial town one of the most rewarding places to explore on the East Coast. It certainly felt that way to me.
About the author:
Jane Smith is a travel writer and history enthusiast who explores destinations through their cultural and historical roots. She’s passionate about uncovering the stories behind places and sharing them in practical, engaging ways. When she’s not writing, you’ll find her wandering historic towns, camera in hand.
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