Maryland is a state that rewards explorers with its diverse landscapes and historic towns, all easily accessible on foot. Its quaint small towns like Berlin, historic North Beach, and Chesapeake Beach offer more than just pretty sights — they invite you to walk through stories of the past, sample local flavors, and enjoy scenic views of Chesapeake Bay. These walking tours combine local history, architecture, and edible treats, making them perfect for travelers who love to combine activity with culture. Whether you prefer a tasting journey, scenic strolls, or exploring historic railway routes, Maryland’s walkable spots have something to delight every visitor.
In this guide, we’ll explore six of the best walking tours in Maryland, each offering its own unique flavor. From the culinary delights of Berlin to scenic bayside walks in North Beach, these tours are perfect for day-trippers, history buffs, and nature lovers alike. Ready to lace up your walking shoes and discover Maryland on foot? Let’s go.
Quick Overview
This list includes a variety of guided walks ranging from culinary tasting tours in charming Berlin to scenic and historic explorations in North Beach and Chesapeake Beach. Whether you’re after a food-focused experience, a nature walk, or a history lesson, Maryland’s walkable destinations have it covered. Each tour provides a unique window into local culture and scenery, with some offering special highlights like historic filming locations or wildlife spotting. For more details, visit each tour page linked above.
1. Berlin Tasting Tour: A Delicious Walk Through History
This 3-hour guided tour in the small town of Berlin combines culinary treats with a deep dive into local stories. Berlin was named one of the 20 best small towns to visit by the Smithsonian, and this walk proves why. You’ll stroll along Main Street, exploring nearly two centuries of architecture while visiting several restaurants and specialty shops. The tour also includes stops at sights featured in the filming of Runaway Bride, giving you a glimpse into Hollywood history right in Maryland.
What makes this tour stand out is its focus on local families and their dishes, offering a taste of Berlin’s heritage and evolving culinary scene. The guide shares fascinating facts about landmarks like the famous equine center, home to legendary thoroughbreds like Man O’ War and War Admiral. Guests consistently praise the friendly atmosphere and the variety of tastings, which make the $110 price reasonable for a well-rounded experience.
Perfect for food lovers, history enthusiasts, and anyone wanting a leisurely exploration of a town crowned the “Coolest Small Town in America,” this tour offers a delicious and informative way to spend an afternoon.
Bottom line: If you want a blend of history, architecture, and good food, this tour is a top pick.
2. North Beach Historic – Guided Walking Tour
At just $41 per person for about an hour to an hour and a half, this tour offers a quick but thorough look at North Beach’s historic charm. Starting at the Welcome Center on the Boardwalk, you’ll stroll along the bayside pier, famous for discovering many entertainer stars. The walk includes historic points of interest and ends at the Bayside History Museum, where you can dive deeper into the town’s past.
While this tour is not rated yet, its focus on local history and waterfront attractions makes it an appealing option for those short on time. Walking past colorful shops, historic homes, and the pier, you’ll get a good sense of North Beach’s coastal character. Note that the tour requires 24-hour advance call to confirm minimum participants, so plan ahead.
If you’re seeking a cost-effective, informative walk that covers the essentials of North Beach’s past and present, this tour fits the bill.
Bottom line: Ideal for visitors with limited time wanting an overview of North Beach’s history and waterfront.
3. North Beach Scenic – Guided Walking Tour
This 1 to 1.5-hour scenic tour shares the same starting point at the Welcome Center on the Boardwalk but emphasizes the natural beauty and scenic spots. You’ll explore Sunrise Garden, the Wetland Overlook Park, and the pier — places where you might spot local wildlife like birds and perhaps even a bald eagle. Along the way, you’ll admire historic homes and cottages that add charm to the waterfront.
The highlight here is its focus on nature and scenery, making it perfect for visitors who want more than just history. The tour concludes with a visit to the Bayside History Museum, providing context for North Beach’s role as a beach destination before the Chesapeake Bay Bridge was built.
This tour suits those interested in outdoor activities, birdwatching, and landscape photography. For $41, it offers an engaging balance of scenery and history.
Bottom line: If natural beauty and wildlife are your priorities, this scenic walk is a great choice.
4. Chesapeake Beach: Guided Walking Tour of the Railway Trail
For around $41 per person, the Railway Trail tour in Chesapeake Beach offers a fascinating glimpse into local transportation history. The 1.5-hour tour begins at Kellam’s Field, where you’ll learn how the Railway Trail helped establish and develop Chesapeake Beach. As you walk along the trail, you’ll enjoy views of marshland and Fishing Creek, with opportunities to observe local wildlife, including bald eagles.
What makes this tour special is its focus on historic infrastructure and nature. You’ll discover how the old railway influenced the town’s growth and learn about conservation efforts, including how to support local wildlife with bat and purple martin houses. The guide shares stories about the trail’s past and its connection to the town’s identity.
This walk is best suited for those interested in local history, nature, and outdoor activity. It’s a good option for families, history buffs, or anyone who enjoys learning about how transportation shaped communities.
Bottom line: A well-rounded experience blending history and wildlife, perfect for active explorers.
5. North Beach: North Beach Historic Guided Walking Tour
At $41 per person for approximately 90 minutes, this historic walking tour offers a deeper look into Chesapeake Beach’s North Beach. Starting at Bay Ave, you’ll walk past historic homes, explore the boardwalk, and discover hidden town gems. The tour also includes a visit to the Bayside History Museum, where you’ll see exhibits about the town’s past as a popular beach destination before the construction of the Chesapeake Bay Bridge.
Highlights include stories about the famous entertainers discovered on the pier and the colorful shops and cafes that line the waterfront. The guide provides context about North Beach’s evolution from a quiet fishing village to a lively seaside town.
This tour is suited for travelers interested in local history, architecture, and coastal charm. It offers a relaxed pace, perfect for those wanting to soak in the town’s character.
Bottom line: An engaging historical stroll that combines local stories with scenic views.
6. North Beach: North Beach Scenic Guided Walking Tour
This scenic version of the North Beach walk shares many highlights with the previous scenic tour but additionally emphasizes water features like the Sunrise Garden and Wetland Overlook Park. It’s a 1.5-hour walk that ends with a visit to the Bayside History Museum to understand North Beach’s pre-bridge history.
The tour centerpieces are the water features and native plants, offering a peaceful and educational experience. You’ll learn about local wildlife, and the walk’s relaxed pace is perfect for those wanting a leisurely exploration of the waterfront.
Ideal for nature lovers, families, or those seeking a calm, scenic experience, this tour balances history and outdoor beauty. The $41 price makes it a compelling choice for a half-day adventure.
Bottom line: A tranquil, scenic walk that combines nature, history, and waterfront charm.
How to Choose the Right Walking Tour in Maryland
When selecting among these options, consider your interests and schedule. Want a culinary adventure? The Berlin Tasting Tour offers a rich mix of food and architecture. Looking for a short, informative overview? The North Beach Historic walk is perfect for a quick introduction. If nature and wildlife top your list, the North Beach Scenic or Railway Trail tours provide immersive outdoor experiences.
Budget is also a consideration. Tours range from $41 to $110, so think about whether you prefer a focused experience or an all-day outing. Always book early, especially in peak seasons, and double-check tour times, as some require advance calls or have limited availability.
Final Thoughts
Maryland’s walkable destinations cater to a wide range of interests. For a culinary journey paired with history, the Berlin Tasting Tour is a standout. For scenic outdoor experiences, the North Beach Scenic or Railway Trail** tours offer a mix of wildlife, water views, and local history.
If you prefer a shorter, town-focused walk, the North Beach Historic gives a well-rounded overview. No matter which you choose, Maryland’s small towns are best explored on foot — so pick your tour, wear comfortable shoes, and enjoy discovering these charming coastal communities at your own pace.
Remember, booking early can help secure your spot on these popular walks. Maryland’s rich and varied walking tours guarantee you’ll leave with more than just a good story — you’ll have a great experience.