Maryland’s most worthwhile walking tours pack centuries of history and natural beauty into compact, enriching experiences.
The standout walks concentrate in two main coastal areas: North Beach and Chesapeake Beach.
The North Beach boardwalk tours perfectly combine antique browsing with local storytelling.
I especially love the morning walks when the shops are just opening and the crowds are thin.
Over in Chesapeake Beach, the Railway Trail tours offer the best blend of maritime history and unspoiled nature – watch for ospreys and herons in the marshlands.
These walks work for most fitness levels, typically lasting 2-3 hours on flat terrain.
Local guides really know their stuff, mixing historical facts with colorful local tales that you won’t find in guidebooks.
Let’s explore the top walking tours worth your time and money in Maryland.
Good To Know
- North Beach Historic – Guided Walking Tour offers a 1.5-hour exploration of historic landmarks and attractions in North Beach, Maryland, priced at $39 per person.
- Chesapeake Beach: North Beach Scenic Guided Walking Tour provides a 1.5-hour guided tour of the town’s natural features, including the Sunrise Garden and Wetland Overlook Park, for $1,046 per person.
- Chesapeake Beach: Guided Walking Tour of the Railway Trail focuses on the area’s railway legacy, featuring educational installations about local wildlife and ecosystem preservation, with a duration of 1.5 hours.
- Chesapeake Beach: North Beach Historic Guided Walking Tour takes visitors along the beachside boardwalk, highlighting the town’s entertainment history and notable attractions, lasting 1.5 hours and costing $44 per person.
- North Beach Scenic – Guided Walking Tour, a 2-hour tour led by Chesapeake Windsail Cruises Corporation, starts at the Welcome Center and ends at the Bayside History Museum, with prices from $39 per person.
North Beach Historic – Guided Walking Tour
Exploring North Beach’s rich history, the North Beach Historic – Guided Walking Tour takes visitors on an immersive journey through the charming coastal town.
Operated by Chesapeake Windsail Cruises Corporation, the tour is priced at $39.00 per person and accommodates a maximum of 16 travelers. The tour begins at the Welcome Center on the Boardwalk and concludes at the Bayside History Museum.
Throughout the tour, you will be provided with water and communication radios for groups of 5 or more. The tour is wheelchair and stroller accessible, and service animals are allowed.
However, it’s not recommended for travelers with certain medical conditions or limited physical fitness. Confirmation is received at booking, and there’s a free cancellation policy up to 24 hours before the experience.
Guests can also take advantage of the “Reserve now, pay later” option for added flexibility.
Read our full review: North Beach Historic – Guided Walking Tour Review
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Chesapeake Beach: North Beach Scenic Guided Walking Tour
The Chesapeake Beach: North Beach Scenic Guided Walking Tour invites visitors to enjoy the coastal charm of North Beach. Priced at Kč1,046 per person, this 1.5-hour tour is limited to just 6 participants, ensuring an intimate and personalized experience.
Guided by knowledgeable English-speaking locals, the tour explores the Sunrise Garden’s water features and native plants, before visiting the Wetland Overlook Park to spot local wildlife.
Delving into North Beach’s history, the tour then takes visitors through the town center, unveiling its hidden gems. The experience culminates with a visit to the Bayside History Museum, where guests can explore exhibits featuring shark teeth, whale bones, and Native American implements.
With a free cancellation policy up to 24 hours in advance, this tour offers flexibility and convenience. Whether seeking to immerse in nature, uncover local history, or simply enjoy a leisurely stroll, the Chesapeake Beach: North Beach Scenic Guided Walking Tour provides a well-rounded and enriching experience.
Read our full review: Chesapeake Beach: North Beach Scenic Guided Walking Tour Review
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Chesapeake Beach: Guided Walking Tour of the Railway Trail
Discover the captivating history of Chesapeake Beach’s railway legacy on this guided walking tour of the Railway Trail.
Led by knowledgeable guides, this 1.5-hour excursion takes you through the forest and marshland along the old railway line, revealing how it contributed to the town’s hotel.
Along the way, you’ll learn about local wildlife, including bald eagles, and discover educational installations that support the local ecosystem, such as bat and purple martin houses.
Explore the medicinal properties of mosquito-repellent plants in the educational garden and gain insights into preserving the region’s natural beauty.
With a minimum of 5 participants required, this tour offers a flexible reserve-now-pay-later option.
Cancellations up to 24 hours in advance are fully refundable, making it an accessible and convenient way to experience Chesapeake Beach’s rich railway heritage.
Meet your guide at the Kellam Field and embark on an immersive journey through the area’s captivating past and present.
Read our full review: Chesapeake Beach: Guided Walking Tour of the Railway Trail Review
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Chesapeake Beach: North Beach Historic Guided Walking Tour
Immerse oneself in the captivating history of North Beach during this 1.5-hour guided walking tour. Priced at $44 per person, this walking tour takes visitors along the beachside boardwalk, where they’ll discover antique shops, gift boutiques, and colorful cafes.
The guide will uncover hidden gems in the town center and share the stories behind the area’s notable entertainment history. Guests will visit the pier where famous entertainers were discovered and admire the beautiful historic homes scattered throughout the town.
The tour culminates with a visit to the Bayside History Museum, where educational exhibits showcase sharks’ teeth, whale bones, Native American implements, seashells, and coral.
This tour is limited to just 6 participants, ensuring an intimate and personalized experience. Cancellation is free up to 24 hours in advance, and reservations can be made now with no upfront payment required.
A live tour guide is available in English, and a minimum of 5 participants is needed for the tour to proceed.
Read our full review: Chesapeake Beach: North Beach Historic Guided Walking Tour Review
Book now: Check availability
North Beach Scenic – Guided Walking Tour
This two-hour guided walking tour of North Beach offers a scenic exploration of the town’s natural beauty and historical highlights.
Led by Chesapeake Windsail Cruises Corporation, the North Beach Scenic – Guided Walking Tour takes visitors on a journey through the charming seaside community. The tour begins at the Welcome Center, located across from the parking lot, and concludes at the Bayside History Museum, just a block away.
Throughout the experience, you will receive clear communication via provided radios and informative handouts. Water is also supplied at the start of the tour.
The moderate physical fitness level required makes this walk accessible to most travelers, though it’s not recommended for those with back problems, pregnant individuals, or those with serious medical conditions.
Priced from $39.00 per person, this private tour can be booked with a minimum of four walkers. Guests are advised to call 24 hours in advance to confirm the tour’s minimum requirement has been met.
Smoking isn’t permitted during the experience.
Read our full review: North Beach Scenic – Guided Walking Tour Review
Book now: Check availability
Questions About Staying Here
How Long Are the Walking Tours Typically?
Walking tours typically range from 1 to 3 hours, allowing visitors to explore the area at a comfortable pace. The duration often depends on the tour’s scope, covering a city’s highlights or delving deeper into its history and culture.
Do the Tours Accommodate Large Groups?
The walking tours typically accommodate large groups, with many offering group discounts and the ability to accommodate groups of up to 25 or more participants. Tour operators are often willing to customize tours for larger parties.
Are the Tours Wheelchair/Mobility Accessible?
Many walking tours accommodate wheelchair and mobility-impaired visitors. Tour operators often provide assistance and accessibility options. Visitors should check with the specific tour company about accessibility accommodations before booking.
Can I Bring My Pet on the Tour?
Whether you can bring your pet on the walking tour depends on the specific tour operator’s policies. Some may allow pets, while others may prohibit them for safety or accessibility reasons. It’s best to check with the tour provider before booking.
Are There Any Age Restrictions for the Tours?
Many walking tour operators have age restrictions, often requiring participants to be at least 8 or 10 years old. Some may allow younger children if accompanied by an adult. It’s best to check with the specific tour company for their policies.
Worth The Stay
Maryland’s coastal towns offer a variety of guided walking tours to explore the region’s rich history and natural beauty. From the historic streets of North Beach to the scenic Railway Trail in Chesapeake Beach, these tours provide an opportunity to discover the unique character of Maryland’s coastal communities. Whether you’re a local or a visitor, these walking tours are a great way to learn about the area’s heritage and natural wonders.