Step back in time with guided history walks through Annapolis, Maryland, exploring its pivotal role in American history and colonial charm.
Annapolis, Maryland, isn't just the state capital; it's a living, breathing testament to America's colonial and revolutionary past. The charming cobblestone streets and beautifully preserved 18th-century architecture whisper stories of signers of the Declaration of Independence, naval heroes, and the very foundations of the nation. Colonial Annapolis History Walks tours offer an immersive way to experience this rich heritage. These expertly guided excursions peel back the layers of time, bringing to life the buildings, events, and personalities that shaped not only Maryland but the United States. Forget dusty textbooks; these tours put you right in the heart of history, allowing you to walk the same paths as figures like George Washington and Thomas Jefferson, who frequented this vibrant port city. Beyond its political significance, Annapolis boasts a distinct maritime heritage. Its prominent harbor and role as a naval hub have left an indelible mark on its landscape and culture. History Walks tours in Annapolis often delve into this seafaring past, revealing tales of privateers, naval academies, and the daily life of sailors and merchants. Whether you're a seasoned history buff or simply curious about the origins of American democracy, these walks provide a captivating and accessible introduction. You'll gain a deeper appreciation for the architecture, the stories behind significant landmarks, and the enduring legacy of this important colonial capital. Prepare to be transported to an era of elegance, revolution, and enduring American spirit.
Discover our top picks for colonial annapolis history walks in Annapolis

During The Historic Annapolis Food Tour, you will enjoy a series of dishes from restaurants in downtown Annapolis while weaving through historic sites. The tour lasts approximately 3.5 hours.

Embark on this Annapolis ghost tour and step back in time as you stroll through the historic district. Your guide will share chilling tales of hauntings at iconic buildings. Discover the restless spirits said to haunt Middleton Tavern, a historic site with numerous ghostly encounters. Throughout the evening, you'll traverse haunted ground, feeling the eerie presence of the spirits rumored to inhabit these locations. This mile-long trek will take you to some of the most haunted and historic sites in Annapolis, including the James Brice House, with its dark past, and the John Brice II House, where former inhabitants are said to still make their presence felt. This walking tour offers an entertaining and immersive experience into Annapolis's haunted history. Perfect for history buffs, or anyone seeking a thrilling evening, this tour promises to captivate and chill. Join us to uncover Annapolis's ghostly past and the spine-tingling stories that have been passed down through generations.

Explore Annapolis' vibrant past on this unique historical pub crawl. Over two hours, discover how drinking influenced the city and the nation while enjoying recommended drinks at each stop. From rebels to rum-runners, each location reveals fascinating stories paired with a drink that defines the era. Perfect for whiskey enthusiasts and history buffs alike, this tour offers a relaxed atmosphere to toast the past and enjoy the present. Dress comfortably as you stroll through downtown, rain or shine, and prepare for a fun evening immersed in tipsy history. - 2-hour historical pub crawl through downtown Annapolis - Discover how drinking shaped Annapolis' history - Enjoy recommended drinks at each stop, not included in the price - Limited walking involved; dress for comfort and the weather

Come on to our Haunted Pub Crawl Tour in Annapolis! Enjoy some liquid courage while hearing ghostly tales of Annapolis' most historic haunts and drinking hotspots. Take a Boo's and Booze Haunted Pub Crawl for genuine stories, scares, and delicious drinks in the historic district, with up to 2 hours of ghostly fun with the city's spirits and Spirits. Price does not include drinks or tastings.

The only Haunted Pub Crawls permitted inside the oldest and most haunted pubs in Historic Downtown Annapolis. Enjoy a 2-hour guided adventure on our haunted pub crawl. Drink in the history, but try not to crawl out the door! Clink glasses with a long-dead barmaid, a "working girl" who'll fall for you, a ghost whose beer has a head even though he doesn't! Join us as we walk from pub to tavern to bar and into the same watering hole, and thru the same streets and alleys as our Founding Father! Hear tales so spooky, "they'll scare ya sober!", lol! Scary? Yes...because they are real! You'll spend about 30 mins at each bar, and your guide will give you plenty of time to purchase a drink or cocktail and then tell you the haunted tales of that location and those nearby. No stories will be told until all guests have their drinks. You'll have time to order and enjoy your drink, use the restroom, and hear the haunted tales! Then on to the next pub, possibly with a stop in the church graveyard!

The original 90-min Annapolis Ghost Tours are the only tours created by our owner, noted local Maryland historian, and author of "Haunted Annapolis". Don't be fooled by national chains pretending to be locally owned and run. Take a nighttime ghost walk through the historic downtown district on a spine-tingling journey into Annapolis’ dark and troubled history. Follow your local guide during this 1.5-hour tour to meet some of the more spirited residents and visiting some of the most horrific haunted sites. Choose from one of various seasonal departure times when you book. NOTE: 7pm & 8pm tours are family friendly if children are present. Language and content toned down accordingly. 9pm tours are considered adult tours, suitable for older children and teens, however there may be some profanity used for effect and adult subject matter.

Get ready to discover why Let’s Roam is the ultimate in app-led adventure hunt excitement! Picture this: strolling through Annapolis, hitting up all the iconic landmarks and uncovering hidden gems, all while tackling trivia questions and conquering challenges with your squad. Whether you’re collaborating with your crew or engaging in some friendly competition, every step is a chance to learn something new and make unforgettable memories. Let’s Roam Adventure Hunts aren’t just for any day — they’re perfect for bachelorette parties that need some spice, birthday celebrations that deserve a twist, or corporate team building events that demand teamwork and laughs. The best part? Each player gets to dive into their own interactive role, with challenges tailored just for them. So, grab your friends, family, or colleagues, pick your roles, and get ready for an epic adventure through Annapolis. Let the games begin — and let the good times roll with Let’s Roam!

Embark on a thrilling adventure in Annapolis! Unravel the city's rich history, from its days as the US capital to its vibrant present. Discover the tales of Princess Anne, Abraham Lincoln, and Duke Ellington. Marvel at the city's architectural wonders, learn about the oldest living people in Maryland, and even snap a selfie with your favorite statue. Uncover secrets of the past and solve riddles that will challenge your mind. This is Annapolis like you've never seen it before! With no set schedule, enjoy the freedom to explore at your own pace using a user-friendly app. Suitable for families, friends, and couples, this unique experience redefines sightseeing in Anaheim.

The Hidden History Pub Crawl is a tour through Annapolis' scandalous past. Sip on a beverage while entertained by stories of historical conspiracies, murder, riots and forgotten tales as your guide brings to life the city’s juiciest stories. With different stories every night, this is the most intriguing experience for Annapolis twisted history. The Hidden History Pub Crawl is a 2-hour Pub Crawl tour (approx. 1/2 mile) into some of the storied taverns of Annapolis. Spending about 20-30 minutes at each location, you'll relax with a cocktail while learning some of our most interesting and colorful history through the tales of our taverns. We will visit three bars on each crawl - locations visited may include some of the following: Middleton Tavern Rams Head Tavern Federal House Dock Street Bar & Grill Drummer's Lot at the Maryland Inn Harry Brownes Galway Bay Drinks are not included in this! This tour is limited to Adults (21+) ONLY! No children.

Explore the captivating history of Annapolis through a unique scavenger hunt walking tour. Delve into the stories of notable figures like Princess Anne and Abraham Lincoln as you navigate the city’s architectural gems. Solve intriguing riddles and uncover hidden secrets at your own pace with an interactive app that guides your adventure. Ideal for families, friends, or couples, this activity offers an engaging way to experience Annapolis like never before, from snapping selfies with iconic statues to learning about Maryland's oldest living residents.
Walk through streets and past buildings that witnessed pivotal moments in American history.
Learn from knowledgeable local guides passionate about Annapolis's colonial narrative.
Admire well-preserved colonial-era buildings and understand their historical context.
Explore sites connected to the American Revolution and the formation of the nation.
Understand Annapolis's significant role as a naval center throughout history.
Capture stunning visuals of historic Annapolis's picturesque streets and waterfront.
These tours provide a comprehensive overview of Annapolis's colonial period, highlighting key events, prominent figures, and significant landmarks. They often cover the State House, the historic market house area, and residential streets showcasing colonial architecture.
Delve into Annapolis's deep connection with the U.S. Naval Academy and its maritime history. Tours may touch upon naval battles, the academy's founding, and the city's strategic importance throughout various conflicts.
Combine a taste of history with a culinary exploration. These tours often visit historic taverns, markets, and eateries, offering insights into the food and drink of colonial times while exploring relevant historical sites.
As dusk settles, explore the darker side of Annapolis's history. These atmospheric walks focus on local legends, ghost stories, and historical mysteries, often visiting supposedly haunted locations.
Most tours typically range from 1.5 to 3 hours in length, offering a good balance of in-depth exploration and manageable walking.
Annapolis experiences all four seasons. Tours are generally held rain or shine, so checking the weather forecast and dressing appropriately is essential. Many operators have policies for inclement weather.
Group sizes can vary, from intimate private tours to larger public walking groups. Smaller groups often allow for more interaction and personalized attention from the guide.
Typically includes the guided walking tour itself. Some specialized tours might include tastings or entrance fees to specific (non-public) historic buildings. Always check the tour details for specifics.
Most tours commence from central, easily accessible locations within historic Annapolis, often near the State House or visitor centers. Clear meeting instructions are always provided upon booking.
Prices generally start around $28 per person for public group tours, with private tours and specialized experiences costing more. Prices are subject to change based on the operator and tour duration.
Wear comfortable walking shoes; Annapolis's historic streets are charming but can be uneven.
Book in advance, especially for popular tours or during peak tourist seasons.
Check the specific meeting point and time for your chosen tour well in advance.
Bring a refillable water bottle, particularly during warmer months.
Don't hesitate to ask your guide questions; they are a wealth of local knowledge.
Consider the time of day for your walk – morning light is beautiful, while evening ghost tours offer a different atmosphere.
Review the tour's cancellation policy, as weather can sometimes impact outdoor activities.
Look for tours that cover specific interests, whether it's the Revolution, maritime history, or culinary traditions.
A: Many general history walks are suitable for older children who can engage with historical narratives. Shorter tours and those with interactive elements might be better. Ghost tours are generally not recommended for very young children due to their spooky nature.
A: Absolutely! These tours offer fantastic photographic opportunities. Guides often point out notable architectural details and scenic vistas perfect for capturing memories.
A: Spring and fall offer pleasant weather for walking, with fewer crowds than summer. The fall foliage can be particularly beautiful. Summer is popular but can be hot and humid, while winter offers a quieter experience.
A: While some tours may have last-minute availability, it's highly recommended to book in advance, especially for popular tours or if you're traveling during peak season. This ensures you secure your spot.
A: Most operators will run tours rain or shine, often with provisions like umbrellas. However, it's always best to check the specific tour operator's cancellation or rescheduling policy in case of severe weather.
A: Annapolis's historic streets can be challenging for wheelchairs due to cobblestones and some inclines. While guides are accommodating, it's crucial to contact the tour operator in advance to discuss accessibility needs and potential routes.
A: A general history walk provides a broad overview of Annapolis's past. Specialized tours, like naval history or culinary walks, delve deeper into specific themes, offering a more focused experience for those with particular interests.
Explore America's sailing capital, rich with maritime history and charming cobblestone streets.
Walk in the footsteps of history at the United States Naval Academy's stunning campus.
Enjoy waterfront dining and boutique shopping with picturesque Chesapeake Bay views.
Immerse yourself in colonial charm and revolutionary spirit evident throughout historic Annapolis.
Experience a vibrant local arts scene and unique events alongside a friendly community.
Discover a quintessential East Coast experience where history meets the water.
Annapolis enjoys a humid subtropical climate, with warm, humid summers and mild to cool winters. Spring and fall offer the most pleasant temperatures, with lower humidity and comfortable conditions ideal for exploring the outdoors. Summers can be quite hot and muggy, while winter brings occasional snow and freezing temperatures.
The best months to visit Annapolis are typically May, June, September, and October, offering delightful weather for outdoor activities and sightseeing without the intense summer heat or winter chill.
Peak season in Annapolis generally runs from June through August, characterized by warm, sunny weather, bustling crowds enjoying the waterfront, and higher accommodation prices.
The off-season, from November to February, sees fewer tourists, lower prices, and cooler weather, offering a more relaxed and intimate experience of the historic city.
Explore comprehensive guides to plan your perfect trip, including food tours, cultural experiences, and more.
Explore Annapolis' vibrant culinary scene and historic pubs on guided food and drink tours, perfect for discovering local flavors and stories.
Discover history, tradition, and the future of naval leadership with expert-led tours of the U.S. Naval Academy.
Discover Annapolis's rich maritime heritage and stunning waterfront views with a variety of engaging tours and activities.
Discover the historic charm of Annapolis and the vast beauty of the Chesapeake Bay aboard a traditional sailing vessel.
Step back in time with expert-led walking tours through Annapolis, a city steeped in American history and maritime charm.
Getting around Annapolis is quite manageable, especially for exploring the historic downtown area. The best way is often on foot, as many key attractions like the Naval Academy, State House, and waterfront are within easy walking distance. For longer distances or exploring beyond the immediate downtown, local bus services are available. Ride-sharing services like Uber and Lyft are also readily accessible. Parking can be a bit challenging and costly in the peak season, so consider utilizing public garages. If you're looking for a scenic journey, water taxis offer a unique way to navigate between different points along the harbor.
Rent a car for maximum flexibility and explore at your own pace on Expedia USA.
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