Top Maryland Walking Tours

Discover Chesapeake Bay cuisine and other dishes on a 3.5-hour small-group walking tour of Fells Point, Baltimore's historic waterfront district. Your guide shares commentary on the history and architecture of the city as you walk through the neighborhood. You'll stop for tastings at four restaurants, and sip a signature alcoholic drink at a fifth establishment. The tour features small local businesses that are popular in the area, and includes one drink and enough food samples to make up a meal. Additional drinks are available for purchase.

Some history-focused city tours can feel stale. Spice up your visit to Annapolis on this guided tour that combines history with food. Visit historic sites and hear fascinating stories while enjoying a series of dishes from downtown restaurants, which may include a tavern frequented by Washington, Jefferson, and Franklin, and a local lobbyists' favorite lunch spot.

Annapolis Walking Tours provides entertaining and informative tours throughout historic Annapolis. This tour is wonderful for people of all ages and involves approximately 2 miles of walking at a relaxed pace with frequent stops. Cobblestone pathways and uneven brick roads are present throughout; please wear comfortable walking shoes and bring appropriate rain gear/ umbrellas in case of rain. Annapolis is the sailing capital of the world; we go outside rain or shine! Tours are offered on the weekends. Additional times may be available with advanced notice. What should you bring? A camera Comfortable shoes Cash (for personal expenses) Important information: Punctuality is important and appreciated. Kindly be at the meeting spot ten minutes before the stated meeting time. The tour guide will wait a maximum of ten minutes before proceeding on the tour.

Explore Great Virginia’s Great Falls Park with this app-based self-guided hiking tour. Discover top highlights and hidden gems, including views of hidden waterfalls, the best rock climbing and rappelling spots, a route through the canals, and an abandoned colonial-era city. The app audio plays automatically using your smartphone’s GPS, making for a seamless way to explore.

Winding through trails, town, and time, this self-guided audio tour explores the powerful stories and landscapes of Harpers Ferry. Over the course of 3 miles, you’ll journey from quiet riverbanks to dramatic ridgelines, past weathered ruins and historic landmarks that shaped the course of American history. This is no ordinary walk—it’s a deep dive into a place where freedom was fought for, ideas were tested, and the nation’s future often hung in the balance. From John Brown’s bold raid to the legacy of Storer College, each stop brings to life a new chapter of ambition, conflict, and change. With GPS-triggered audio guiding your way, you can explore at your own pace—pausing for a scenic view or reflecting at a historic site. Whether you’re a history lover, a curious traveler, or just here for the beauty, this tour offers a moving and memorable way to experience Harpers Ferry.

This tour is all about the real Baltimore, the one shaped by sports, industry, invention, authors and community. Along the way, you’ll see statues that celebrate hometown heroes, a clock tower that once guided the city’s time, a dental museum that’s more fascinating than it sounds, a historic market, and yes — Edgar Allan Poe’s grave. All not to be missed sites. And for this price? It's the best deal in town. This tour is on our walking tour app, it's location aware, smartphone guided, hands free, go at your own pace, not big groups, and go anytime.

Baltimore's Fell's Point neighborhood is filled with great places to eat. But, if you are new in town, it can be difficult to find the best spots. This tour guides you through the historic district, visiting family-run restaurants along the way to sample specially made dishes including Polish, Baltimore-style pit beef, and Spanish tapas.

Step back in time on this 2-hour guided walking tour through the beautifully preserved Historic District of Annapolis, Maryland. Visit the Maryland State House, once the capitol of the United States, and explore a colonial kitchen and dining room inside a stunning Georgian mansion. Stroll past iconic landmarks including St. Anne's Parish, the Hammond-Harwood House, the Paca House, and the lively Annapolis City Dock. Hear the fascinating story of the friendly rivalry between the U.S. Naval Academy and St. John's College, two institutions that have shaped the character of this unique city. Along the way, your guide will bring everyday colonial Maryland life to vivid detail, from the merchant class to the working poor. Covering less than a mile on foot, this tour is an accessible and immersive introduction to one of America's most historic cities.

Find out all about the haunted side of Baltimore and its dark history on this walking tour of the Fell’s Point neighborhood. Learn about the spirit of Edgar Allen Poe and his mysterious death along the way. You’ll be stopping at several pubs/bars/saloons, the cemetery, and a hotel, where you’ll hear tales of the haunted places from your guide along the way.

Select a one hour preset tour or let us make a custom tour for you! Choose from Fells Point: The oldest and saltiest neighborhood in Baltimore, she's paved with Belgium Block streets, European architecture, great eateries and shops. Here Frederick Douglass made his bold escape to freedom and Ann Bond Fell turned a thriving shipyard into one of the most sought after neighborhoods in 1800's America. Fells Point is a charmer. Mount Vernon Place: Considered the most beautiful of Baltimore neighborhoods, Mount Vernon Place was once home the more millionaire philanthropists than any other city in America and it shows. Marble churches, libraries, and monuments are filled with Tiffany glass windows and stories of the movers and shakers who built them. A real eye candy tour. Inner Harbor: The heartbeat of Baltimore, it's chock-a-block full of history, Gilded Age architecture, and quirky characters. Includes the only Outsider Museum in America. Fascinating history in the water and out.

Set on the Chesapeake Bay at the mouth of the Severn River, the picturesque town of Annapolis features some 17 miles of shoreline. This makes it the perfect home of the United States Naval Academy—and thousands of other boating enthusiasts. But there’s much more to this place than just sailing. On this tour, we’ll examine the Revolutionary roots of Annapolis and meet some of the founding fathers who lived and visited here. We’ll explore the town’s role in America’s dark history of slavery and the Civil War, while also highlighting the miraculous accomplishments of free Black Marylanders in the eighteenth and nineteenth centuries. NOTE: This is a self-guided outdoor walking tour. Your purchase does not include entrance to any attractions highlighted on the tour.

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

Patterson Park is a rare blend of natural beauty, history, and everyday neighborhood life, often called the city’s “Best Backyard.” On this self-guided walking tour, you’ll find out how the park – which stretches across more than 130 acres in the heart of East Baltimore – has served Baltimoreans for over two centuries. You’ll also hear how it began as farmland, then became a defensive stronghold during the War of 1812, and why today it remains one of Baltimore’s most cherished public spaces. You’ll pass the Monument honoring Revolutionary War hero Casimir Pulaski, and wind your way over Harris Creek, one of Baltimore’s “ghost rivers” that’s now hidden underground. You’ll see the mile-long earthworks built by residents to prevent the British from attacking the city. You’ll also walk where President Abraham Lincoln ordered troops to camp while keeping peace after pro-Confederate residents threatened more violence after the Pratt Street Riot of 1861.

Hear about Annapolis’s ghostly past with the help of a tour guide who’ll share historical spooky stories. From the spirits said to haunt Middleton Tavern to the dark past of James Brice House, you’ll explore a side of the city most tourists never see. Even though the subject matter may be dark, your tour leader will make sure you’re suitably creeped out, but still having fun.

IMPORTANT UPDATE (3/11/26): The Naval Academy is not currently letting visitors on the Yard for security reasons. Tours currently will focus on the Harbor and colonial downtown. Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor. We'll see the Georgian mansions, the iconic Maryland State House, and much more as you learn the fascinating story of the town. We'll see 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 explore the campuses of two institutes of learning that have shaped American culture. We'll walk along the city dock, harbor, and see the view to the Chesapeake Bay and wider world. I'll also share personal and family stories along the way, to add a personal dimension to the tour. I welcome all questions and special interests for our tour!

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.

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.

Step into the role of detective in a thrilling murder mystery Solve 10–15 interactive puzzles and riddles Explore Baltimore with a GPS-guided storyline Perfect for couples, families, or groups of friends Play anytime, pause and resume at your own pace

⭐ 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.

As an historic city, Annapolis has plenty of haunts. Explore Annapolis oldest and most-ghosted neighborhood on this tour of the historic downtown district, where hundreds of years of history were made. While you walk to neighborhood sights like the Maryland State House and haunted graveyards, your guide shares stories of purported paranormal activity and the real stories behind each.

The historic Baltimore neighborhood of Federal Hill is filled with great eateries but, for visitors, it can be tricky to pick a place. This guided tour takes you through the area and into some of the best spots so that you can fully appreciate the heritage, history, and food scene. Includes tastings at each location.

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.

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.