Maryland is a state that packs a punch when it comes to history. With its mix of colonial sites, seaside towns, and storied neighborhoods, it offers plenty for those eager to learn about America’s past without the crowds of more famous destinations. One of our favorite ways to explore Maryland’s authentic character is through local historical tours, which often combine sightseeing with a taste of regional flavors and stories. For example, the Berlin Tasting Tour stands out for its blend of history, architecture, and delicious bites, giving visitors a chance to see why this charming town was crowned the “Coolest Small Town in America.” Another highlight is the North Beach Guided Walking Tour, which offers a lively stroll along the Chesapeake Bay with stops at historic homes and the famous pier.
Whether you prefer a leisurely afternoon exploring small towns, a walk along scenic boardwalks, or enjoying local stories, Maryland’s selection of historical tours has a lot to offer. These experiences combine engaging guides, authentic sights, and sometimes even local snacks, making the history come alive in a very real way.
Quick Overview
Our list focuses on Maryland’s best historical tours, each offering a unique window into local life and past events. The options include immersive small-town walks with a culinary twist, a scenic boardwalk tour with historic highlights, and a flexible, shorter tour for those with limited time. Check out the tours below and see which one suits your interests and schedule.
1. Berlin Tasting Tour: A Delicious Walk Through History
At number 1, the Berlin Tasting Tour offers a delightful mix of food, architecture, and stories that make this small town a standout. This 3-hour walking tour costs about $110 per person and is rated a perfect 5 out of 5 stars based on 8 reviews. It’s perfect for travelers who want to see a slice of Maryland’s inland charm without sacrificing a good meal.
You’ll start on Main Street, where the town’s nearly two centuries of architecture are on display. The guide shares stories about families who settled here, and you’ll visit sites used in the filming of “Runaway Bride,” adding a Hollywood touch. But the real highlight is tasting the regional specialties at several local restaurants and specialty shops, which showcases how food ties into the community’s identity. The tour also touches on the famous equineline training center, home to legendary racehorses like Man O’ War.
This tour is an excellent choice if you want a relaxed pace, plenty of tastings, and a chance to see why Smithsonian recognizes Berlin as one of the “20 best small towns to visit.” It’s ideal for food lovers, architecture enthusiasts, and anyone curious about small-town Maryland life.
Bottom line: A tasty, well-rounded introduction to Maryland’s charming small towns, with enough history and flavor to leave you wanting more.
2. North Beach: North Beach Historic Guided Walking Tour
Second on our list is the North Beach Historic Guided Walking Tour, which costs $41 per person and lasts about 1.5 hours. While it doesn’t have a star rating yet, it’s a solid choice for those wanting a quick but meaningful look at this seaside town’s past.
This tour takes you along the lively boardwalk and pier, where you’ll hear stories about entertainers discovered there and learn about the development of Chesapeake Beach. You’ll pass by colorful shops, cafes, and historic homes, providing a glimpse into the community’s evolution. The guide also shares insights into the Bayside History Museum, where you can further deepen your understanding of the area’s maritime and leisure history.
What makes this tour stand out is its combination of scenic sights and storytelling. It’s perfect for visitors with limited time who want to combine a walk, some local culture, and history in one short outing. The tour ends at the Bayside History Museum, giving you an opportunity to explore more if you wish.
Bottom line: An efficient way to get a feel for North Beach’s historic charm and seaside vibe in under two hours.
$41 per person
3. North Beach Historic – Guided Walking Tour
The third option, the North Beach Historic – Guided Walking Tour, offers a flexible, hour-long exploration of the same compelling sights. It begins at the North Beach Welcome Center and includes a stroll along the boardwalk, a visit to the pier, and a tour through the town’s historic points of interest, ending at the Bayside History Museum.
This tour demands a minimum of four participants and requires a phone call 24 hours in advance to confirm. The itinerary is similar to the second tour but is designed for those who want a shorter, more intimate experience. It emphasizes the entertainment history of the pier and the beautiful homes around town, providing a relaxed yet informative outing.
While reviews are currently unavailable, this tour is best suited for travelers on a tight schedule or those who prefer a more personalized, small-group experience. Be sure to confirm the minimum number of participants beforehand.
Bottom line: A good option for a quick, guided walk through North Beach’s key historic sights, especially if you prefer a smaller group.
$41.00 per person
How to Choose Your Maryland Historical Tour
When selecting a tour, consider your budget, available time, and interests. For food and architecture lovers, the Berlin Tasting Tour offers a comprehensive experience with tastings and local stories. If your goal is a scenic seaside stroll packed with local lore, the North Beach Guided Tour provides a lively, informal overview. For those with limited time or seeking an intimate group setting, the shorter North Beach Historic Tour could be ideal.
Think about the kind of experience you want—whether it’s a leisurely culinary walk, a quick scenic jaunt, or a deeper dive into Chesapeake Bay’s maritime history. Booking early is recommended, especially for popular tours in peak seasons, and check if any tours require advance confirmation or minimum participants.
Final Thoughts
Maryland’s diverse range of historical tours makes it easy to find an experience that fits your style. From exploring a charming small town with great food to enjoying a seaside walk filled with stories of entertainers and historic homes, there’s something for every history enthusiast. For a full day of discovery, the Berlin Tasting Tour is a standout for its combination of architecture, culture, and cuisine, while those short on time might prefer the more compact North Beach Guided Tour.
Remember, booking in advance will help ensure you don’t miss out, especially during busy weekends or holiday seasons. Whether you’re in town for a quick visit or planning a laid-back getaway, these tours will give you a meaningful glimpse into Maryland’s lively past and local character. Enjoy your explorations!