A Walking Tour of Frederick, Maryland – The Crossroads of Maryland

Discover Frederick, Maryland's history with this engaging 2-hour walking tour led by knowledgeable guides. Perfect for history lovers and curious travelers.

Getting a good sense of a city’s soul often means walking its streets, and in Frederick, Maryland, this approach pays off. While we haven’t personally strolled through this particular tour, it’s clear that this two-hour walk offers a well-rounded glimpse into Frederick’s past, from its early days to its Civil War significance. If you’re considering a way to explore Frederick but want a guided experience that’s both informative and leisurely, this tour could very well hit the spot.

What we love about this tour is the depth of knowledge the guide brings—you’re not just walking around, but learning stories that make history come alive. Plus, at just $15 per person, it offers solid value for those interested in a rich, educational experience without breaking the bank. On the flip side, it’s a walking tour, so if you’re not comfortable on your feet for a couple of hours, or if the weather’s bad, you might want to think twice or look for alternatives.

This tour seems best suited for history buffs, architecture enthusiasts, or anyone curious about Frederick’s heritage. It’s also flexible enough to adapt for those interested in themed topics like Civil War history or architecture, making it a versatile way to spend a couple of hours in this charming town.

Key Points

A Walking Tour of Frederick, Maryland - The Crossroads of Maryland - Key Points

  • Affordable Price: At $15, it’s a budget-friendly way to explore Frederick with a knowledgeable guide.
  • In-Depth Content: The tour covers a broad range of landmarks and stories, giving a well-rounded picture of Frederick’s history.
  • Flexible Options: Can be customized with themes or virtual options during bad weather.
  • Comfortable Pace: Slow enough for most, including older walkers, with a focus on storytelling and visuals.
  • Small Group: Max of 12 travelers, ensuring a personalized experience.
  • Weather-Resilient: Can be done rain or shine, with indoor options if needed.

Exploring Frederick Through Its Historic Stops

The tour begins at Winchester Hall, an essential site with roots stretching back to the 18th century. Here, the guide offers a brief overview of Frederick’s evolution from its founding in 1745 through the Civil War to today. Seeing a 180-year-old girls’ school that still exists today adds a tangible sense of continuity. Many reviews highlight the guide’s extensive knowledge, with comments like “This is an in-depth tour of the town,” and “He has interesting stories about the old homes around the town.” Expect to learn about the architecture, key historical events, and notable figures that shaped the city.

Next, a quick stop at Heritage Frederick introduces you to the Loats Female Orphan Asylum and Protestant Episcopal Orphan Home. Although these orphanages no longer operate, their legacy endures through scholarship foundations supporting disadvantaged youth. The short visit emphasizes how institutions can leave a lasting mark on a community.

The Evangelical Lutheran Church provides insight into Frederick’s religious roots, with the guide explaining the congregation’s nearly 300-year history and the significance of the Twin Spires landmark. Expect some discussion about Civil War-era engineering and architecture, which many visitors find fascinating. As one reviewer puts it, the church offers “great German engineering during the Civil War,” adding a layer of technical interest to the story.

Moving on, the Evangelical Reformed United Church of Christ marks the start of Frederick’s German immigrant story. You’ll learn how John Thomas Schley and a modest congregation transformed Frederick from a mere settlement into a bustling crossroads of Maryland. The guide’s storytelling makes these early days of the city vivid, capturing how a group of immigrants turned destiny.

The City Hall of Frederick and Courthouse Square serve as the political and civic heart of the city. Here, stories swirl around legends like the accidental burning of the second courthouse and the intriguing ties to Francis Scott Key and Roger Brooke Taney. Numerous reviews praise the guide’s ability to weave these stories into a compelling narrative, with mentions of “many points of interest” covered in nearly a 360-degree view.

The Barbara Fritchie Legend is a highlight for many, with the story of the patriotic woman during the Civil War told with enthusiasm. It’s a quick stop but a memorable one, especially for those interested in Civil War lore. As one reviewer notes, the stories about Fritchie added a personal, human touch to the historical landscape.

A leisurely stroll along Carroll Creek Linear Park offers scenic views, an ideal moment to breathe in the city’s vibe. The park’s aesthetic and the surrounding sights provide a visual break and a chance to enjoy Frederick’s charm.

Baker Park then introduces visitors to a green space that’s central to city life today, offering a sense of how Frederick balances history and modernity. The tour ends with a walk through Historic Downtown Frederick, home to colorful architecture, bustling shops, and stories of a city that has weathered floods, industry booms, and revitalization.

How the Tour Works

A Walking Tour of Frederick, Maryland - The Crossroads of Maryland - How the Tour Works

This guided experience lasts approximately two hours and covers about 1.2 miles, making it accessible for most fitness levels. The small group size—a maximum of 12 travelers—ensures a personalized experience and plenty of opportunities for questions. The tour is bi-directional, starting at 17 E Church St and returning there or nearby, making it convenient for participants.

The price of $15 is quite reasonable considering the depth of knowledge, the number of landmarks visited, and the flexible options available, including themed or indoor tours if weather is uncooperative. The tour runs year-round, with light rain or snow no problem, but heavy weather could lead to indoor alternatives or cancellations, with full refunds available if that happens.

What Visitors Are Saying

A Walking Tour of Frederick, Maryland - The Crossroads of Maryland - What Visitors Are Saying

The reviews echo a lot of what’s been shared here. Many praise Don, the guide, for his extensive knowledge, engaging storytelling, and friendly demeanor. One reviewer mentions, “Don was very knowledgeable, and I learned new things,” even though they’d lived in Frederick for some time. Others appreciate the slow pace, making it easy for older visitors to keep up and enjoy the stories without feeling rushed.

Some feedback points out the value of the small group size, with one comment highlighting how private tours allow for a more tailored experience. Even those who were already familiar with Frederick’s history still learned new details, underscoring the tour’s depth. One less glowing review mentioned that Don could improve by making the presentation more organized or engaging, but this seems to be the exception rather than the rule.

Many reviews emphasize the storytelling aspect—how the stories about Civil War figures, legends, and historic buildings make the past come alive. The guide’s ability to connect different landmarks into a cohesive narrative makes the two hours feel packed with information but still relaxed enough to enjoy the walk.

How Does It Compare to Other Experiences?

Compared to other local attractions, this tour offers a more immersive, storytelling-driven approach rather than just a checklist of sights. It’s ideal for those who love history, enjoy architecture, or just want to learn about Frederick from a local perspective. The fact that it can be customized with themes like churches or Civil War history makes it adaptable for various interests.

The price point is fair, especially considering the personalized attention and the wealth of stories shared. For those who prefer a more casual or self-guided walk, there are other options, but none with the same depth and personal touch that the guide provides here.

Who Should Consider This Tour?

This walking tour is especially well-suited for history and architecture enthusiasts, curious travelers wanting to understand Frederick’s roots, and those who enjoy storytelling. It’s perfect if you’re visiting Frederick for the first time or if you’re local but want a fresh perspective on your city.

If you’re traveling with someone who prefers a low-pressure, relaxed pace and enjoys learning through stories rather than just seeing sights, this is a good fit. The tour’s flexible options, including indoor alternatives during bad weather, mean you can still get a meaningful experience no matter the forecast.

Final Thoughts

A Walking Tour of Frederick, Maryland - The Crossroads of Maryland - Final Thoughts

For just $15, this tour offers a well-curated, personable way to dive into Frederick’s past and present. The combination of a knowledgeable guide, interesting stories, and accessible stops makes it one of the more compelling options for exploring the city’s history on foot.

Whether you’re a civil war buff, an architecture lover, or simply someone keen to understand why Frederick is called the Crossroads of Maryland, this tour provides a balanced, engaging experience. It’s a great way to spend a couple of hours soaking up stories and sights you might otherwise miss during a casual stroll.

If you’re looking for a relaxed, informative, and personal look into Frederick’s past, this tour is worth considering.

Ready to Book?

A Walking Tour of Frederick, Maryland – The Crossroads of Maryland



4.5

(53)

“This is an in-depth tour of the town of Frederick. The host has extensive knowledge of the city and the role the town played in the civil war. He …”

— Rebecca P, Apr 2025

FAQ

How long does the tour last?
The tour runs for about two hours, covering roughly 1.2 miles, making it a manageable walk for most.

What is the group size?
The maximum number of travelers is 12, ensuring a more personal experience.

What’s the cost?
It costs $15 per person, which is quite reasonable given the depth of stories and landmarks covered.

Can I do the tour if it’s raining?
Yes, light rain or snow is okay, and the tour can be done as planned. In heavy weather, indoor virtual options are available for groups of 8 or fewer.

Is the tour suitable for older travelers?
Yes, many reviews mention the slow pace and comfortable walking distance, making it suitable for older visitors.

Are there themed tours available?
Yes, upon request, the tour can focus on themes like churches, architecture, Civil War, or even photo shoots.

Where does the tour start and end?
It begins and ends at 17 E Church St, Frederick, MD 21701, making it convenient to access.

Is there a refund policy?
Yes, you can cancel up to 24 hours in advance for a full refund, and weather-related cancellations are fully refundable.

If you’re interested in exploring Frederick’s streets and stories with a friendly guide who knows his stuff, this tour seems like a solid choice. It combines history, community, and a good dose of storytelling—all for a very fair price.