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Annapolis Historic District

4.8
·39 reviews·Annapolis, United States

Step back in time in Annapolis, Maryland's charming colonial capital, with its historic streets, waterfront, and U.S. Naval Academy.

Highlights

Highlights

Must-see attractions

Social content

Social

From TikTok & Reddit

Best Time

Fall Mornings

Crisp air, fall colors

CrowdMedium
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Annapolis Historic District - a building with a sign on it

Annapolis Historic District

Best Time

Fall Mornings

Crisp air, fall colors

CrowdMedium
Highlights

Highlights

Must-see attractions

Step back in time in Annapolis, Maryland's charming colonial capital, with its historic streets, waterfront, and U.S. Naval Academy.

4.8
(39 reviews)

"Annapolis is worth a special trip to see. Its colonial ambiance and historic sites are carefully guarded."

Vertical photo
TIP

🚶‍♀️ Wander the Streets

Explore the charming colonial streets and admire the historic architecture.

⚓️ Admire the Sailboats

The City Dock and Ego Alley are perfect for boat watching.

Third hero image

Highlights

Discover the most iconic attractions and experiences

Historic District Stroll

Historic District Stroll

Downtown Annapolis

Wander through charming streets lined with 18th-century brick homes and colonial architecture.

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U.S. Naval Academy

U.S. Naval Academy

Annapolis

Explore the grounds of this prestigious institution, rich in tradition and history.

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Annapolis City Dock & Ego Alley

Annapolis City Dock & Ego Alley

Annapolis Harbor

Experience the maritime heart of Annapolis, with stunning sailboats and waterfront views.

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Maryland State House

Maryland State House

State Circle

Visit the oldest state capitol still in legislative use, a cornerstone of American history.

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Planning Your Visit

Embrace the Colonial Charm

Wander through the Annapolis Historic District to step back in time. Explore cobblestone streets and 18th-century architecture. Consider visiting during the fall for a picturesque experience with crisp air and colorful foliage. TikTok

Naval Academy & Waterfront Wonders

Don't miss the U.S. Naval Academy, open to the public, and the vibrant Annapolis City Dock. Enjoy the maritime atmosphere and admire the impressive sailboats. Instagram+1

Best Times

When
Fall Mornings
Why
Crisp air, fall colors
Crowd
Medium
When
Weekday Afternoons
Why
Fewer crowds, relaxed pace
Crowd
Low
When
Holiday Evenings
Why
Festive decorations
Crowd
High

Insider Tips

from TikTok, Instagram & Reddit

Soon Annapolis will look like this! 🍁✨ 📍 Downtown Annapolis, Maryland USA 🇺🇸 The streets will soon be glowing with color and crisp fall air will make wandering this historic city even better. 🍂😍 Some of the best spots for autumn strolls: 🍁 Main Street 🍁 Annapolis City Dock 🍁 Prince George St. 🍁 State Circle 🍁 School Street 🍁 West Street Annapolis always feels special this time of year full of char...
@jaytravelsworld
29.6K likes • 136.4K views

🚶‍♀️ Wander the Streets

Explore the charming colonial streets and admire the historic architecture. Instagram+1

⚓️ Admire the Sailboats

The City Dock and Ego Alley are perfect for boat watching. Instagram

This might be the most underrated city … #midatlantic #eastcoast #navy #annapolis #travel #travelbucketlist #roadtrip
@_ashtinevans
11.8K likes • 148.3K views
European vibes… in Maryland? 🇺🇸✨ Top 6 Things to Do in Annapolis: * Maryland State House – the oldest state capitol still in legislative use 🏛️ * Wander the Historic District – pastel colonial homes and peaceful lanes 🏘️ * Stroll Main Street – cafés, boutiques, and historic inns ☕🛍️ * Tour the U.S. Naval Academy – open to the public, rich in tradition ⚓🎓 * Visit the William Paca House & Gardens ...
frenchiesontrip
395 likes • 6.3K views

📚 Browse Unique Shops

Discover boutiques and local stores along Main Street. Instagram

🍽️ Savor Local Flavors

Annapolis boasts top-rated restaurants and historic taverns. InstagramReddit

3 reasons to visit Annapolis Maryland ⚓️🇺🇸🛥️. . 1. Rich maritime history and beautiful waterfront. 2. Charming historic district with unique shops and restaurants. 3. Vibrant arts scene with festivals and cultural events. . #annapolis #annapolisphotographer #annapolismaryland #annapolismd #annapolisrealestate #annapolisrealtor #maryland #marylandrealestate #visitannapolis #naptown
360.t.o.u.r.s
33 likes • 924 views

Tips

from all over the internet

🚶‍♀️ Wander the Streets

Explore the charming colonial streets and admire the historic architecture. Instagram+1

⚓️ Admire the Sailboats

The City Dock and Ego Alley are perfect for boat watching. Instagram

📚 Browse Unique Shops

Discover boutiques and local stores along Main Street. Instagram

🍽️ Savor Local Flavors

Annapolis boasts top-rated restaurants and historic taverns. InstagramReddit

📅 Check for Events

Look out for local markets and festivals for a vibrant experience. TikTok

What Travellers Say

4.8
(39 reviews)

Reviews Summary

Visitors consistently praise Annapolis for its beautiful historic architecture, charming streets, and vibrant waterfront. The city offers a delightful blend of colonial ambiance and modern amenities, with excellent dining options and a welcoming atmosphere. While some find parking challenging, the overall experience is highly regarded as a worthwhile destination. InstagramReddit

"Nice buildings. Make sure to take a look at the plates to learn some history"

Pil G

"Very cool area. The marina has some serious boats in it. Lots of fun shops and restaurants. Also took the harbor tour and it was very fun and interesting to learn the history and significance of the parts of the harbor."

Chris Plath

"Annapolis is worth a special trip to see. Its colonial ambiance and historic sites are carefully guarded, but this is also a working town. It's not so much like Williamsburg in Virginia as it is more like a smaller Charleston, SC or perhaps like Portsmouth, NH. Make a special effort to see the historic houses in the town. And by all means, stay overnight and appreciate the restaurants and taverns. You'll find that Annapolis is so much more than just the Naval Academy."

Jon L Albee

What People Like

Historic colonial charm
Beautiful waterfront
Great restaurants

What People Dislike

Parking can be difficult

Frequently Asked Questions

🚇 🗺️ Getting There

Annapolis is about a 45-minute to 1-hour drive from Washington D.C. TikTok Parking can be challenging, so consider using public garages or ride-sharing services. Reddit

Yes, the Annapolis Historic District is very walkable. Most attractions are within easy reach on foot. Instagram

Walking is ideal for the historic district. For a broader perspective, consider a harbor tour. Reddit

While walking is primary, local buses and water taxis can be useful for getting around different parts of the city. Reddit

Absolutely! Annapolis is a popular day trip destination from both cities, offering a charming escape. TikTok+1

🎫 🎫 Tickets & Entry

The historic district itself is free to explore. However, specific attractions like museums or tours may have admission fees. Instagram

The U.S. Naval Academy grounds are generally open to the public, but specific tours or buildings might require tickets or have access restrictions. Check their official website for the latest information. Instagram

The Maryland State House is typically open to visitors during business hours, but it's best to check their official website for current hours and any special closures. Instagram

Wandering the historic streets, enjoying the waterfront, and admiring the architecture are all free activities. Instagram+1

Harbor tours are popular and offer great views. You can also find guided walking tours focusing on history. Reddit

🎫 🧭 Onsite Experience

Key sites include the Maryland State House, the historic homes, and the U.S. Naval Academy. Instagram+2

Ego Alley is a narrow waterway leading from the harbor into downtown, famous for showcasing impressive sailboats. Instagram

Yes, the colonial architecture, waterfront views, and charming streets offer numerous picturesque spots. Instagram

You'll find a mix of boutiques, antique shops, and unique local stores, especially along Main Street. Instagram

Absolutely! Annapolis is steeped in colonial history, with well-preserved buildings and significant historical sites. Instagram+2

🍽️ 🍽️ Food & Dining

Annapolis has a great food scene, with options ranging from seafood at The Choptank TikTok to Italian at Vin 909.TikTok Iron Rooster is known for breakfast. TikTok

Yes, being a coastal town, Annapolis offers excellent seafood options, including The Choptank. TikTok

Yes, there are many casual eateries, coffee shops like Old Fox Books and Coffee House,TikTok and sandwich spots like The Ugly Pig. TikTok

The waterfront area offers a variety of restaurants with scenic views, perfect for enjoying a meal. Instagram

Annapolis has a rich history of taverns and pubs that offer a taste of the past along with food and drinks. Reddit

📸 📸 Photography

The historic streets, Maryland State House, City Dock, and Ego Alley provide stunning photographic opportunities. Instagram+1

Golden hour (early morning and late afternoon) offers beautiful light for capturing the colonial charm. TikTok

Look for the 18th-century brickwork, colonial-era doorways, and the unique cupolas of historic buildings. Instagram

Photography policies can vary within the Naval Academy. It's advisable to check their guidelines before visiting. Instagram

Its well-preserved colonial architecture, maritime atmosphere, and picturesque waterfront create a visually rich environment. Instagram

For Different Travelers

Tailored advice for your travel style

👨‍👩‍👧 Families with Kids

Annapolis offers a family-friendly experience with its walkable historic district and engaging attractions. Kids will enjoy exploring the grounds of the U.S. Naval Academy and imagining life as a midshipman. Instagram A harbor tour is also a great way to keep everyone entertained while learning about the city's history and seeing the boats. Reddit Many of the shops and restaurants along Main Street are welcoming to families, and the open spaces around the City Dock provide room to run around. Consider visiting during a local event or festival for added excitement. TikTok

💰 Budget Travelers

To enjoy Annapolis on a budget, focus on the many free attractions. Wandering the historic streets, admiring the architecture, and enjoying the waterfront views at the City Dock cost nothing. Instagram+1 Pack a picnic to enjoy by the water, or seek out casual eateries and coffee shops for more affordable meal options. TikTok+1 Look for free events or markets, like the Naptown Flea, which can offer unique finds without a high entry cost. TikTok Walking is the best way to get around, saving on transportation costs. Reddit

🏛️ History Enthusiasts

Annapolis is a dream destination for history buffs. The Annapolis Historic District is a living museum, with the Maryland State House being a paramount site. Instagram+1 Explore the U.S. Naval Academy for its rich military history and impressive architecture. Instagram+1 Seek out guided tours that delve into the stories of the colonial era, the Founding Fathers, and the city's maritime past. Reddit Visiting historic homes and museums will provide deeper insights into the lives of those who shaped this significant American city. Instagram

Deep Dives

In-depth insights and expert knowledge

Navigating the Annapolis Historic District

The Annapolis Historic District is a treasure trove of colonial history, characterized by its well-preserved 18th-century architecture and cobblestone streets. Wandering through areas like Main Street, State Circle, and Prince George Street offers a tangible connection to the past. TikTokInstagram+1 Many of the buildings here have served as homes, government offices, and businesses for centuries, each with its own story. The district is remarkably walkable, allowing visitors to immerse themselves in the atmosphere at their own pace. Instagram

Key landmarks within the district include the Maryland State House, the oldest state capitol in continuous legislative use in the United States, and numerous historic homes that offer glimpses into colonial life. Instagram+1 The U.S. Naval Academy, though a separate entity, is adjacent to the historic district and a significant draw for visitors, showcasing impressive architecture and military traditions. Instagram+1 The Annapolis City Dock and the famous Ego Alley are also integral parts of the downtown experience, bustling with sailboats and offering scenic waterfront views. Instagram

For those interested in a deeper dive, consider taking a guided walking tour that can illuminate the historical significance of specific buildings and events. Reddit Alternatively, exploring on your own allows for spontaneous discoveries, from charming boutiques to historic taverns that have been serving patrons for generations. InstagramReddit The district truly offers a step back in time, making it a unique destination for history enthusiasts and casual travelers alike. Instagram

Culinary Delights of Annapolis

Annapolis is a culinary hotspot, renowned for its diverse dining scene that ranges from fresh seafood to classic American comfort food. The city's proximity to the Chesapeake Bay ensures an abundance of high-quality seafood, with restaurants like The Choptank offering a taste of Maryland's maritime heritage. TikTok For those seeking a more intimate dining experience, Vin 909 in Eastport is frequently praised for its delicious offerings, including its popular arugula and prosciutto salad. TikTok

Beyond seafood, Annapolis caters to all tastes. Iron Rooster is a go-to spot for all-day breakfast and American comfort food, TikTok while Old Fox Books and Coffee House provides a cozy atmosphere for a coffee and a browse. TikTok For a quick and satisfying bite, places like The Ugly Pig offer great sandwiches, showcasing the city's commitment to quality local fare. TikTok Many of the historic taverns and restaurants in the district also provide a unique ambiance, allowing diners to savor their meals while surrounded by centuries of history. Reddit

When planning your culinary journey, consider exploring the various neighborhoods, as each offers its own distinct flavor. Whether you're looking for a fine dining experience or a casual meal, Annapolis promises a memorable gastronomic adventure. InstagramReddit

Experiencing the Maritime Charm

Annapolis is famously known as the 'Sailboat Capital of the World,' and its maritime spirit is palpable throughout the city, especially around the Annapolis City Dock and Ego Alley. Instagram+1 This vibrant waterfront area is a hub of activity, where you can witness a stunning array of sailboats and yachts docked or cruising through the narrow waterway. The sight of these vessels against the backdrop of historic buildings creates a picturesque scene that is quintessentially Annapolis. Instagram

A harbor tour is a highly recommended way to fully appreciate the city's connection to the water. These tours offer not only beautiful views of the skyline and the U.S. Naval Academy from the water but also provide fascinating insights into the city's rich maritime history and its significance. Reddit Many visitors find these tours to be a fun and informative way to learn about Annapolis's past and its ongoing relationship with the Chesapeake Bay. Reddit

Beyond the dock, the maritime influence is felt in the city's culture, from its seafood-centric cuisine to the general atmosphere of a historic port town. Even a simple stroll along the waterfront allows you to soak in the salty air and the lively energy of this coastal gem. Instagram

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