Maryland is a surprisingly walkable state, offering a mix of historic towns, scenic waterfronts, and lush parks—all perfect for exploring on foot. Unlike many states, Maryland’s small towns, like Berlin and North Beach, shine brightest when you stroll their streets, discovering stories behind the storefronts and enjoying local flavors. Our favorite? The Berlin Tasting Tour because it combines history, charming architecture, and delicious bites, making it a well-rounded experience for anyone curious about small-town Maryland.
For those interested in a more nature-oriented walk, the Chesapeake Beach Railway Trail offers a lovely blend of marshland views and local wildlife. And if coastal charm is what you seek, the North Beach Guided Tours reveal the town’s colorful history and scenic waterfront spots. Whether you’re after history, nature, or a bit of both, Maryland’s walking tours deliver authentic experiences in compact, walkable settings.
Quick Overview
Our list features five top walking tours across Maryland, each with its own unique appeal:
– A culinary and historic stroll through Berlin (Berlin Tasting Tour)
– A nature and history walk along the Railway Trail in Chesapeake Beach (Chesapeake Beach Railway Trail)
– Two North Beach tours focusing on history and scenic views (North Beach Historic Tour and North Beach Scenic Tour)
– A shorter, more flexible North Beach Historic Tour with a focus on local sights (North Beach Historic)
Now, let’s explore each in detail to help you choose the best fit.
1. Berlin Tasting Tour: A Delicious Walk Through History
At number one, this tour combines culinary delights with a walk through one of Maryland’s most charming small towns, Berlin. Named one of the 20 best small towns to visit by the Smithsonian, Berlin offers a picture-perfect Main Street lined with nearly two centuries of architecture, making it an ideal setting for a leisurely stroll. The tour lasts about three hours and costs $110 per person, which, considering the number of tastings and insights, offers good value.
What sets this tour apart is its ability to blend food and history seamlessly. You’ll visit several restaurants and specialty shops, sampling regional treats that reflect the local families and traditions. Along the way, a guide shares stories about the historic families, the town’s development, and even fun movie trivia—Julia Roberts and Richard Gere filmed Runaway Bride right here. Plus, you learn about the nearby equine center where famous racehorses like “Man o’ War” and “War Admiral” lived and trained.
Guests often comment on the well-paced itinerary, which allows enough time to savor each treat without feeling rushed. The highlight for many is the chance to see why Berlin has earned the nickname “Coolest Small Town in America”. This tour is perfect for food lovers, history buffs, and anyone seeking a relaxed, authentic taste of small-town Maryland.
Bottom Line: A delightful mix of food, history, and scenery in a top-rated town—ideal for a half-day outing.
2. Chesapeake Beach: Guided Walking Tour of the Railway Trail
Coming in at number two, the Chesapeake Beach Railway Trail tour is a solid choice for nature lovers and history enthusiasts alike. For just $41 per person, this 1.5-hour guided walk takes you along the historic Railway Trail, which played a vital role in shaping the town’s development. The trail offers marshland views and vistas of Fishing Creek, providing a peaceful setting to learn about the area’s past.
Your guide shares stories about the trail’s significance, from its role in establishing Chesapeake Beach to the regional impact of the railroad. Along the route, you’ll also get a chance to observe local wildlife like bald eagles and learn about native plants used in mosquito control. The educational garden onsite is a bonus for those interested in sustainable practices and supporting local ecosystems.
What makes this tour particularly appealing is its interactive approach to ecology and history, making it suitable for families and nature seekers. It’s a great way to combine light exercise with education, especially if you enjoy spotting wildlife and learning how the town grew from a tiny fishing village.
Bottom Line: An engaging, short walk that blends regional history with natural beauty—perfect for those who want a relaxed, educational outdoor experience.
$41 per person
3. North Beach: North Beach Historic Guided Walking Tour
Number three on our list is the North Beach Historic Guided Tour, a 1.5-hour stroll through the town’s colorful past. For $41 per person, this walk is perfect if you want a quick but comprehensive look at North Beach’s history and local sights. The tour begins at the Welcome Center and takes you along the boardwalk, past the pier, and through historic neighborhoods filled with beautiful homes.
Your guide shares stories about how the town became a popular summer destination, highlighting famous entertainers discovered at the pier. Educational exhibits at the Bayside History Museum give a deeper understanding of North Beach’s evolution. Along the way, you’ll see charming shops and cafes that add to the town’s lively atmosphere.
While the tour doesn’t delve deeply into every aspect of the town, it offers enough insight for a quick visit. It’s well-suited for families, history lovers, or anyone wanting a snapshot of North Beach’s vibrant past.
Bottom Line: A concise, engaging walk that covers the essential sights and stories of North Beach, ideal for a brief visit.
$41 per person
4. North Beach: North Beach Scenic Guided Walking Tour
If you’re craving scenery and nature combined with local history, this 1.5-hour tour hits the mark. For $41 per person, you visit Sunrise Garden, Wetland Overlook Park, and the waterfront district, each offering native plants, water features, and wildlife spotting opportunities.
Your guide discusses the native plant species and water features that define the town’s natural environment. You’ll also hear about the history of North Beach and how its waterfront has shaped community life. The tour concludes with a visit to the Bayside History Museum, where you can explore exhibits about the area’s past.
This tour is best suited for nature enthusiasts and those interested in local ecology. It offers a more relaxing pace than the historic walk, with plenty of opportunities to stop and enjoy the scenery.
Bottom Line: A scenic walk that combines gardens, wetlands, and history—great for those who love the outdoors and peaceful settings.
$41 per person
5. North Beach Historic – Guided Walking Tour
Rounding out the list, this shorter, flexible tour focuses on the historic points of interest around North Beach, including the pier, boardwalk, and town landmarks. It’s a 1 to 1.5-hour walk costing $41 per person, with the added note that you need to call 24 hours in advance to confirm minimum group size.
Starting at the Welcome Center on the boardwalk, the tour takes you through famous entertainment spots and historic homes. It concludes at the Bayside History Museum, providing a nice wrap-up of the town’s story. The tour emphasizes local architecture and well-known sites, making it a good choice if your schedule is tight or if you prefer a shorter, more focused experience.
Keep in mind that the museum’s operation hours are not guaranteed, so plan accordingly. This tour is ideal for first-time visitors or those with limited time but wanting a solid overview.
Bottom Line: A compact, informative tour that captures North Beach’s historic vibe, suitable for a quick introduction.
$41.00 per person
How to Choose the Right Maryland Walking Tour
When selecting a walking tour in Maryland, consider your interests and schedule. If you love culinary experiences and small-town charm, the Berlin Tasting Tour will suit you perfectly—plus, it’s rated 5.0/5 based on 8 reviews. For a blend of nature and history, the Railway Trail walk offers a peaceful outdoor experience with wildlife spotting and educational stops. Those looking to explore coastal history and scenic waterfronts will enjoy the North Beach tours, especially the scenic guided walk.
Think about your time commitment—the longest tour is around three hours, while the others are typically an hour and a half or less. Budget-wise, all tours are reasonable, with prices ranging from $41 to $110. Booking early, especially for popular tours like Berlin’s, is advisable to ensure availability.
In sum, Maryland offers a variety of walkable experiences suited for foodies, nature lovers, history buffs, and coastal explorers alike. Whether you want to sample local treats, learn about the town’s past, or enjoy the natural surroundings, there’s a tour that will fit your interests. Remember to check the tour websites for current schedules and availability to make the most of your visit.
Maryland’s charm on foot is undeniable, whether wandering historic towns or scenic parks. For history and flavor, the Berlin Tasting Tour is a standout. If nature is your priority, the Railway Trail walk delivers serenity and wildlife encounters. And for coastal scenery and local stories, the North Beach tours provide a delightful glimpse of this Maryland seaside community.
Whatever your choice, these tours promise an authentic, enjoyable way to see Maryland’s diverse small towns and natural beauty. Book early, lace up your walking shoes, and enjoy the journey.