Top Maryland Walking Tours - page 2

Stroll through Baltimore's Fells Point neighborhood while hearing ghost stories on this spooky tour. With a guide providing eerie tales as you walk, stop at some of the most historic and haunted landmarks in the neighborhood. You'll come away with a deeper understanding of the neighborhood's history and its grisly past, facts you might not otherwise learn on traditional tours.

Discover the profound legacy of African American history in Maryland on an enlightening two-hour walking tour in Annapolis. Starting near Market House Park, journey through time to encounter significant landmarks such as the Alex Haley statue and the Maryland State House while learning about the vital contributions of historic figures including Harriet Tubman, Frederick Douglass, and Thurgood Marshall. Led by a knowledgeable guide in period attire, this experience delves into the local history, culture, and stories of the Underground Railroad, with tour proceeds directly supporting the Kunta Kinte-Alex Haley Foundation to enhance community heritage.

Drink your way through the haunted side of historic Fells Point on Spirits of Fells Point, Baltimore’s adults-only haunted pub crawl. Along the route, guests will visit atmospheric bars and historic streets while hearing stories of Edgar Allan Poe, vanished sailors, smugglers, gamblers, haunted taverns, waterfront crime, and the bad decisions that helped give Fells Point its notorious reputation. This is more than a night out at the bars. It is a haunted walk through the places where sailors once spent their wages, privateers and merchants chased fortunes, and legends of restless spirits still linger near the harbor. Guests will have time to purchase drinks at select stops while enjoying spooky storytelling, local lore, and a fun social atmosphere. Perfect for adults who want ghosts, history, drinks, and a little chaos, Spirits of Fells Point offers a memorable way to experience Baltimore after dark. Guests must be 21+ with valid photo ID.

Step into the shadows of historic Fells Point on the Baltimore Ghost Tour, where the city’s haunted past is tied to the harbor that built it. Led by an engaging Ghost City Tours Ambassador, this tour takes guests through one of Baltimore’s oldest waterfront neighborhoods, a place once filled with sailors, shipbuilders, dockworkers, taverns, boarding houses, and travelers from around the world. As the streets grow darker, you’ll hear chilling stories of haunted hotels, vanished sailors, mysterious figures near the water, and the restless spirits said to linger along Baltimore’s historic harbor. Along the way, explore stories connected to the Admiral Fell Inn, the Thames Street waterfront, The Horse You Came In On Saloon, and walk through the lasting mystery of Edgar Allan Poe’s final days in Baltimore. This tour blends spooky storytelling, local legend, and historically inspired tales into an atmospheric walk through one of the city’s most character-filled neighborhoods.

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complimentary non-alcoholic beverage during the cruise before spending around three hours ashore exploring the town before the return journey to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included, making this sightseeing day trip an ideal way to experience Maryland's rich maritime history.

Your tour will take you through the historic downtown area known as Old Towne, where Victorian-style buildings and century-old businesses tell the incredible story of the "Petticoat Regime"—the pioneering women who owned and operated 30 out of 32 hotels by 1926. We'll start at the Ocean City Life-Saving Museum near the inlet and walk north along the Boardwalk and Baltimore Avenue, ending at the famous Thrasher's French Fries stand.You will hear stories about remarkable businesswomen like Zipporah "Zippy" Lewis, who lived in a house made from shipwreck wood and left her land to her daughters instead of her sons, and Ella Phillips Dennis, who along with other women, created one of America's most successful female-dominated business communities during an era when women weren't even allowed to vote. Go at your own pace, anytime. This tour is smartphone guided and never expires. It's all on your walking tour app.

From the National Aquarium to one of the wildest Super Bowls ever played, a mayor who swam in a seal pond to the only Outsider Art Museum in the country, the Civil War to a sinking hill Baltimore's Inner Harbor riches to rags to riches story has something for everyone. Starting at The Civil War Museum this walking tour ends at The American Visionary Art Museum, whose gift shop John Waters says is the best anywhere. Chock-a-block full of all-ages history and things to see and do and eat

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.

Put a ghoulish twist on your night out with a haunted pub crawl through historic Annapolis. Visit three bars over the course of the night, each with a ghost story behind it that will scare you sober. Drinks available at your own purchase.

Explore Baltimore after dark for a different, darker perspective on Charm City. With a guide leading the way, skip the planning and get hear about the city's spooky side at several popular pubs and haunted sites. Start at Max’s Taphouse before continuing to other notorious watering holes, and uncover more eerie local history than you could on your own.

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Baltimore, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.

This lighthearted, adults-only, tongue-in-cheek, walking tour is presented by a guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet – colonial style. During your walking tour in Historic Annapolis, you’ll hear scandalous anecdotes and jaw-dropping tales about what went on inside Annapolis’ famed homes and taverns. Colonial Founding Fathers, Annapolis gentry, renowned portrait artists, and regular folk, too, were all up to their tricks! There was revenge, murder, spying, drinking, political discord, and pleasures of the night.

Explore the eerie side of Annapolis with the Spirits & Spirits tour, blending a captivating walking tour through the Historic District with a thrilling cruise on the haunted waterways. Listen to spooky stories from your Ghost Guide, uncover nautical myths, and indulge in beverages available for purchase during the cruise. Perfect for those seeking a unique blend of history and ghostly tales in a fun atmosphere. This tour is suitable for adults and private tours can be arranged upon request. - Combination of a guided walking tour and a scenic ghost cruise. - Hear chilling tales from expert Ghost Guides while exploring Annapolis's Historic District. - Enjoy a variety of beverages and snacks available for purchase once on the boat. - Tours available on select dates, departing from 188 Main Street, Annapolis.

THIS TOUR CAN BE TAKEN VIA COACH: email for pricing Take the tour that introduces you to brilliant, bold Baltimoreans who changed the course of history. Whether paving political inroads or planning daring escapes, these iconic women made their own destinies, turning vision into reality, oppression into opportunity. Whether by faith, family name, personal fortunes, or sheer grit these women made history you'll never forget. Let these bad boss babes inspire and amaze you while exploring the sites where it all went down.

The tour includes a stroll on the board walk, the pier where famous entertainers were discovered, the town & historic points of interests and will end in the Bayside History Museum. Just a few of the sights on the tour. You must call 24 hours before your tour time to see if the minimum requirement of 4 walkers has been met.

Explore the Antietam National Battlefield, the site of the bloodiest single day in American military history. This self-guided driving tour traces the pivotal battle of September 1862, allowing you to discover key sites like Dunker Church and Burnside Bridge at your own pace. Utilize GPS-triggered narration that brings historical stories to life as you navigate through serene landscapes that witnessed fierce combat. Reflect on the sacrifices made here and understand how this battle influenced the Emancipation Proclamation and the future of the nation. - Self-guided driving tour with GPS-triggered narration - Visit historic sites including Miller Cornfield and Bloody Lane - Flexible exploration: take your time at various landmarks - Total tour duration of 2 to 4 hours, designed for easy stops along the route

Baltimore’s Black history hidden in plain sight. Walk the actual streets where slavery, freedom-seeking, resistance, Black institution-building, and the first blood shed in the Civil War collided. Through expert storytelling, archival context, and place-based interpretation, discover Harriet Tubman, Frederick Douglass, Nicholas “Nick” Biddle, and the free Black communities that helped shape the nation.

Welcome the holidays with Watermark's Christmas in the Capital Tour: Annapolis Traditions and State House Trees. Meet your period-attired guide inside our cozy office before embarking on your tour. Stroll with your colonial guide around Maryland’s capital city, trimmed in greenery for the season. Hear holiday traditions of times past and present as you walk by colonial mansions, Victorian homes, and quaint shops A highlight of the tour is the Maryland State House, with decorated Christmas trees representing the different counties of Maryland, presented by the Federated Garden Clubs of Maryland. The tour ends at Annapolis's grand Christmas tree at Market House Park. Take home the holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe!

A leisurely stroll through OC's famous local restaurant and bar scene, combined with history, local lore and fun fascinating facts about this coastal gem of a town and the family's who started here. Includes tastings at 6 local eateries. Come hungry and leave full. Walk, Eat, Drink, Learn... Repeat

Learn about Ocean City and the family's who started here. You will learn how the inlet was formed creating Assateague island and how OC became the White Marlin Capital of the world. Taste your way through some of the top places while your local guide shares fun facts about this coastal gem of a town.

Discover the quirky tales and unusual stories of Annapolis on this engaging walking tour. Led by a colonial-attired guide, explore fascinating anecdotes including the Russian sailor's grave in the Annapolis National Cemetery and the Confederate captain who never conceded defeat. Perfect for those curious about the unconventional side of history, this tour reveals the city's hidden gems and eccentric past. Ideal for adults and middle school-aged children, the tour takes place at 188 Main Street, Annapolis, MD. - Duration: 1 hour and 15 minutes - Suitable for adults and children aged 12 and older - Tours run on the second Saturday of each month - Learn about unique historical figures and events in Annapolis

Trace David Simon's scathing critique of American urban governance on foot across Baltimore. Contrast the marble domes of downtown political power, courthouses, and legacy newsrooms with the physical realities of West Baltimore's low-rises, classrooms, boxing rings, and social clubs. Experience how municipal budgets and institutional self-preservation shape the daily rhythm of life on the street corners. - A 6.9 km self-guided tour with 8 stops and 1 audio interlude over 183 min - Ideal for travelers interested in Power, Protest & Civic Spaces and Social Fabric & Everyday Life - Immersively told in a podcast style by experts and locals - Matching audio content, AI guide and navigation through the app

Take a pleasant walking tour through the beautiful historic center of Annapolis, specially designed for the US 250th Anniversary. Discover the fascinating role Annapolis played in the fight for and achievement of American independence! We will begin along the city dock and harbor that received many founding fathers in the 1700's, admiring the view to the Chesapeake Bay and wider world. We'll see two Georgian mansion built in the 1770's, as well as the iconic Maryland State House, where the Treaty of Paris was signed (bringing to a conclusion the Revolutionary War) and where General Washington resigned as general, thus becoming the "greatest man in the world" and the "American Cincinnatus. " We'll also explore the campus of St. John's College, which dates back to 1696, and talk about other Annapolis customs and traditions, as well as bars, restaurants, and more. All questions are welcome!

This private walking tour offers a calm and comfortable introduction to historic Annapolis at an easy pace. You explore the city as residents once did, along flat streets and quiet waterfront paths shaped by daily life and civic tradition. Clear storytelling brings forward the voices of merchants, lawmakers, families, and sailors who defined early Annapolis. Your walk begins near the harbor where trade and community met. The route continues through peaceful public spaces with time to pause, sit, and enjoy the surroundings. Stories focus on early American governance, maritime heritage, and local customs explained in a relaxed and engaging way. This experience suits travelers aged 50+ who value culture, history, and thoughtful narration without rushing. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.