Your Ultimate Historic Walking Tour of Annapolis

Ultimate Walking Tour of Historical Annapolis

Beth Glosner  | 

If cobblestone streets, secret alleys, and 18th-century charm sound like your kind of adventure, you’re in the right place. Annapolis, Maryland, may be the state’s capital, but it feels more like a storybook town. This blog is your go to walking guide for exploring it on your own two feet. Whether you’re here for the weekend or just a day, get ready to step back in time and see the city like never before. Let’s Dig In.

Disclaimer

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here

Walk Through History: The Fast Guide to a Perfect Self-Guided Tour

Annapolis is best explored slowly and with eyes wide open. Here’s how to build a perfect walking tour:

  • Start at City Dock: The heart of town, packed with boats and photo ops.
  • Stroll up Main Street: Shops, coffee spots, and colonial buildings.
  • Visit the Maryland State House: The oldest in continuous use. Yes, George Washington actually walked these halls.
  • Wander Pinkney Street: It’s like stepping onto a Revolutionary War film set.
  • End at the William Paca House & Gardens: Peaceful, elegant, and totally Instagrammable.
George Washington was here

Pro Tip: Annapolis is super walkable, but the cobblestones are no joke. Comfortable shoes are a must.

Let the Architecture Talk to You

If buildings could gossip, Annapolis would be the juiciest town in America. The city’s architecture is a visual time machine, offering a look into the past through brick and mortar and walking provides the perfect way to explore it.

Don’t Miss:

Annapolis homes have curb appeal.

Pro Tip: If you’re short on time but love architecture, take a Historical House Tour. Download the” GPSmyCity: Walks in 1K+ Cities” app, and you have a personal guide in your hand.

Ghosts, Legends & After-Dark History

Want your history with a side of spooky? Annapolis has ghost tours that walk the line between goosebumps and giggles. Tours start at dusk and wind through haunted alleys and graveyards.

Spooky Stops Include:

It’s getting spooky..

Pro Tip: Book your tour in advance, especially in fall. These fill up fast, and you don’t want to be left in the dark.

Short on Time? Try This 2-Hour Loop

If you’re just here for a few hours and want the highlights, here’s a breezy, 2-hour walking route:

  1. Start at Ego Alley (City Dock)
  2. Main Street > State House
  3. Pinkney Street > St. Anne’s Church
  4. Tour the Hammond-Harwood House
  5. End at the Paca House Gardens for a snack or picnic
Your Ultimate Historic Walking Tour of Annapolis
One city, so many stories waiting on every block.

Pro Tip: The Circulator Trolley is free and handy if your feet give out. It loops all the key stops.

Make the Most of Your Walk

  • Stop into historic taverns for a mid-walk refreshment
  • Pack a picnic for the Paca Gardens or Spa Creek
  • Bring a reusable water bottle (there are fountains!) at the docks and St. John’s College
  • Snap pics of historical markers and quirky alleyways
Not all alleys are scary 

Pro Tip: Morning walks are quieter, cooler, and perfect for photos without photobombers.

Ready to Take a Step Back in Time?

Annapolis isn’t just history in books — it’s under your feet, around every corner, and above your head. Whether you want to stroll solo or go full-on guided tour, there’s a route that fits your mood and your time. So lace up your comfy shoes, bring your curiosity, and see where the bricks lead you. If you need a pick-me-up during your walking journey, here are some coffee places to stop by and fuel up.

Do you have a favorite historic spot in Annapolis? Share it in the comments or tag your walk with #HistoricAnnapolisWalk. I’d love to see your journey through time.

Stay curious, stay hungry, and keep exploring!


-Beth
Sunset in Annapolis: Best Waterfront Drinks & Golden Hour Experiences

Sunset in Annapolis: Best Waterfront Drinks & Golden Hour Experiences

Beth Glosner  | 

Golden Hour, Annapolis Style: Where Sails, Spirits, and Sunsets Shine

If you’re looking for the perfect way to wind down your day in Annapolis, it doesn’t get better than a sunset cruise and a cocktail. Whether you’re on a classic schooner or sipping local spirits at a dockside café, this historic town knows how to toast the sunset. Consider this your insider’s guide to golden hour on the water — where to sail, sip, and soak up the best views in town.

Let’s dig in.

Disclaimer

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here

Why Annapolis Does Sunset Better

With its historic harbor, charming waterfront, and nonstop sailboat sightings, Annapolis is practically made for sunset lovers. But the trick is knowing where to be when the sky turns to gold. The locals know it’s not just about the view — it’s about the vibe: music playing, sails catching the last breeze, a cold drink in hand.

In this guide, we’ll break down:

So whether you’re planning a date night, a group hangout, or a solo adventure, Annapolis delivers big-time beauty with plenty of buzz.

Set Sail on the Schooner Woodwind

The Schooner Woodwind is Annapolis’s gold standard for sunset cruises. This 74-foot sailing yacht lets you experience the Chesapeake Bay the way it was meant to be — with the wind in your hair and a front-row seat to the setting sun. The crew even lets guests help raise the sails!

Sunset, salt air, and smooth sailing.

Pro Tip: Book early, especially for Friday and Saturday cruises. The best spots sell out fast during warm months.

Preserve: Seasonal Sips and Thoughtful Bites Near the Harbor

Just up Main Street from the waterfront, Preserve offers a fresh, locally driven menu and some of the most creative cocktails in town. With a modern farmhouse vibe and standout service, it’s the perfect spot to start or end your golden hour walk. Try a rotating seasonal spritz or one of their house infusions — and don’t skip the Preserve Pickles appetizers (a local favorite).

Fresh and local

Pro Tip: Head to the water before or after dinner — you’re just steps from the harbor and prime sunset photo ops.

Level: Cozy Café Vibes with a Craft Cocktail Twist

If you prefer a stylish lounge over a rowdy taproom, Level :A Small Plates Lounge, is your spot. Just a short walk from the harbor, Level serves up inventive cocktails in a cozy-chic setting. Their drink menu rotates seasonally, with options like elderflower spritzes, bourbon infusions, and zero-proof mocktails for non-drinkers.

Not into beer? Sip something smarter at Level..

Pro Tip: Make a reservation for a table on weekends — their small plates pair perfectly with a craft cocktail.

Bonus: DIY Sunset Picnic on the Docks

Not into crowds? Pack your own snacks and drinks and find a bench along Susan Campbell Park, right at the edge of the harbor. It’s low-key, beautiful, and free. You’ll get the same epic views as the bars without the bar tab.

Pro Tip: Bring a small Bluetooth speaker for tunes — but keep it low and mellow. You’re not throwing a rave.

Your Golden Hour Game Plan

Whether you’re sailing into the sunset, sipping rum by the dock, or enjoying a hand-crafted cocktail under soft lighting, Annapolis sunset experiences are hard to beat. It’s the kind of moment that makes you stop, breathe, and smile.

Ready to plan your perfect Annapolis evening? Book that cruise, text your crew, and find your spot on the dock. And if you’re looking to turn golden hour into a golden day, don’t miss my blog 24 Hours in Annapolis: Perfect Day Trip—it’s your guide to soaking up every last drop of this charming town.

Just don’t forget to tag your favorite moments with #SipAndSailAnnapolis.

Stay curious, stay hungry, and keep exploring!

-Beth
Exploring Annapolis' Hidden Historical Sites

Exploring Annapolis’ Hidden Historical Sites

Beth Glosner  | 

Discover Annapolis’ Rich and Untold Past

Annapolis is often celebrated for its iconic spots: the Maryland State House, the U.S. Naval Academy, and the bustling harborfront. But the city has more to offer than just its well-known landmarks. What if I told you that some of the most fascinating pieces of Annapolis’ history are hidden in plain sight? The city’s rich past stretches far beyond the tour bus routes, from secret gardens to ghostly haunts and Revolutionary War sites. Ready to step off the beaten path and uncover some of Annapolis’ best-kept secrets?

Let’s dig in.

Disclaimer

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here

Uncovering Revolutionary War Secrets

If you consider yourself a history buff, you probably know about Annapolis’ central role during the American Revolution. But beyond the famous sites, lesser-known treasures are waiting for discovery.

One such place is The Hammond-Harwood House, an elegant Georgian mansion that dates back to the 1770s. This house hosted important figures during the colonial era, including George Washington and Thomas Jefferson. Hidden in its walls are stories of the region’s role in shaping the nation. While most tourists head straight to the Maryland State House, this mansion offers a quieter and just-as-enlightening glimpse into Annapolis’ revolutionary past.

Pro Tip: Take a guided tour to explore the mansion’s hidden secrets you wouldn’t catch alone. Trust me, the historic details will blow your mind.

Hammond-Harwood House –  where history whispers from every corner.

Colonial Charm in the Heart of Annapolis

While most tourists flock to the State House or the bustling shops around City Dock, Pinkney Street offers a more peaceful, yet equally historic, experience. This charming, cobblestone street is often overlooked but holds incredible stories of Annapolis’ colonial days. Walking down Pinkney Street feels like stepping back in time, with colonial-era homes and quaint gardens that give you a true sense of the city’s past.

Tucked away on Pinkney Street, the Hogshead Trades Museum offers an immersive glimpse into 18th-century life in Annapolis. This unassuming wooden structure, painted a rich colonial red, once served as lodging for itinerant workers and tradesmen, and today, it serves as a portal to the past.

The museum is part of Historic Annapolis’ Museum Without Walls initiative, which offers self-guided tours and interactive storytelling across the city. At Hogshead, that storytelling is particularly vivid—you might find yourself watching a reenactor stitch a haversack or explaining how sailors bartered for supplies. It’s not just a museum visit; it’s time travel.

Pro Tip: Pinkney Street is best explored early in the morning or late afternoon when the light is soft, and you can take in the historic beauty in peace.

A glimpse of Annapolis’ colonial past.

Haunting History

Ready for a thrill? Annapolis is a city steeped in history, and that means there are plenty of stories that still echo through its streets. Many of the city’s oldest buildings have their own ghostly tales, and if you’re up for a spooky adventure, ghost tours are a must-do.

Start with the Annapolis Ghost Tours, which take you through the streets and alleys, highlighting haunted buildings and giving you an eerie insight into the city’s supernatural past and even haunted pub crawls, if you dare. Whether it’s the whispers in the William Paca House or the shadows in St. Anne’s Cemetery, these tours will make you feel like you’re walking among history—and the spirits that still linger.

Pro Tip: For a truly spooky experience, opt for the nighttime tour, which immerses you in the mood with low lighting and haunting stories.

Annapolis after dark for a ghostly stroll through history’s most haunted spots

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The Hidden Garden of the Maryland State House: A Quiet Escape

While the Maryland State House is a must-see, most visitors never venture beyond its grandeur. However, behind the State House, you’ll find a hidden gem: the State House Garden. This peaceful oasis is tucked away and often overlooked by tourists who are more focused on the building’s exterior and history.

This garden, dating back to the 1700s, was once the site of political gatherings and social events. Today, it serves as a quiet retreat, with its lush greenery and stunning views of the Chesapeake Bay. The perfect spot for reflection, the garden offers a glimpse into the calming beauty that’s been an integral part of Annapolis for centuries.

Pro Tip: Pack a light picnic, grab a seat on the stone bench, and let the garden’s serenity help you unwind during your historic tour. But remember to pick up after yourself.

Peace in the hidden garden behind the Maryland State House

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A Hidden Treasure of Naval History

While the U.S. Naval Academy is a popular attraction, another spot on the water is often missed: the Annapolis Maritime Museum. This hidden gem dives deep into Annapolis’ maritime history, showcasing the area’s transformation from a colonial seaport to a center for naval and military innovation.

Located in the Eastport neighborhood, the museum offers exhibits on the area’s fishing heritage, its role in the War of 1812, and the evolution of the Chesapeake Bay’s shipbuilding industry. If you’re a fan of maritime history or want a deeper look at Annapolis’ connection to the water, this museum is an essential stop.

Pro Tip: Check the museum’s calendar for special events, like boat tours or hands-on workshops, to enhance your experience.

Dive into Annapolis’ naval past.

A Deeper Dive into History

For those truly looking to immerse themselves in Annapolis’ hidden history, booking a private or small-group tour with a local guide can make all the difference. Local guides know the nooks and crannies of Annapolis that most visitors miss, from forgotten stories of the colonial era to the secrets behind the city’s architecture. Plus, they can take you to sites that are off the beaten path, giving you a deeper, richer experience of the city.

Pro Tip: Look for tours that focus on specific themes—like Annapolis’ maritime past, ghost stories, or colonial history—to get the most out of your experience.

For a more personalized experience, book a local guide to uncover Annapolis’ hidden history.

Ready to Uncover Annapolis’ Hidden Past?

Annapolis is brimming with history, and while many of the city’s famous sites are certainly worth seeing, some of the most fascinating stories are waiting for you off the beaten path. From hidden Revolutionary War spots to secret gardens and ghostly tales, this charming city has so much more to discover.

Looking for even more ways to explore? Don’t miss Time Travel on Foot: Your Ultimate Historic Walking Tour of Annapolis—a guide to experiencing the city’s rich past.

So, what are you waiting for? Start planning your own historical journey through Annapolis and uncover the treasures that lie just beneath the surface.

Stay curious, stay hungry, and keep exploring!


–Beth