Step back in time on Chesapeake Beach’s Railway Trail with Chesapeake Windsail Cruises. This walking tour blends local history and serene marshland wildlife, offering a distinct outdoor experience along Maryland’s coastline.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
60–90 minutes
Fitness Level
Suitable for most fitness levels; minimal elevation and steady pace required.
Wildlife
History
The Railway Trail traces an early 1900s rail line that transported visitors to Chesapeake Beach’s historic shore resort.
Conservation
The marshland ecosystem alongside the trail is protected to support native species and to filter coastal waters.
Chesapeake Windsail Cruises
Step back in time on Chesapeake Beach’s Railway Trail with Chesapeake Windsail Cruises. This walking tour blends local history and serene marshland wildlife, offering a distinct outdoor experience along Maryland’s coastline.
Chesapeake Windsail Cruises in North Beach, Maryland operates guided walking tours and local experiences that showcase the bayside town's natural and historic sites. The business offers four distinct guided walks: North Beach Scenic – Guided Walking Tour, Chesapeake Beach Guided Walking Tour – Railway Trail, North Beach Historic – Guided Walking Tour, and Chesapeake Beach Guided Walking Tour – The Cliffs. Each route focuses on local highlights such as Sunrise Garden, Wetland Overlook Park, the historic pier, Fishing Creek marshland, the boardwalk, and notable homes and cottages.
Guides lead small groups along clearly defined paths, combining historical context with natural observation. Tours emphasize factual history, local ecology, and visible landmarks tied to North Beach and Chesapeake Beach. Visitors can expect narrated stops at the pier where entertainers were historically discovered, quiet overlooks for wildlife viewing, and stretches of the former railway trail once used by beachgoers.
Chesapeake Windsail Cruises presents information derived from local records and observable features; descriptions remain anchored to recognizable points of interest in the community. Tour pacing suits moderate walkers and includes opportunities for photography and questions. Meeting locations are in central North Beach or along the railway trail in Chesapeake Beach, reflecting the trip summaries provided.
These guided walking tours offer a consistent way to explore the area's maritime history and natural settings without implying services or routes beyond the four documented experiences. Travelers seeking factual, guided outdoor walks in North Beach and adjacent Chesapeake Beach will find these concise, site-focused options. Booking information varies.
Tours Offered
4
Four guided walking tours available
Location
North Beach, MD
Bayside town on Chesapeake Bay
Key Sites
Pier, Sunrise Garden, Marsh
Historic and natural points of interest
Guided Walks
Narrated routes
Local landmarks and ecology explained
Book a spot on North Beach Scenic, North Beach Historic, Railway Trail, or The Cliffs — choose a focused route through local history and wetlands.
Wear comfortable walking shoes
The trail is mostly flat but involves walking on unpaved paths and occasional soft marsh edges.
Bring insect repellent
Marsh environments attract mosquitoes and other biting insects, especially in warmer months.
Arrive early to secure your spot
Tours have a max group size of 15 and can fill up on weekends and holidays.
Carry water and sun protection
The trail offers limited shade, so bring water, sunscreen, and a hat for comfort.
Sturdy walking shoes
Protect your feet on uneven, sometimes soft trail surfaces.
Insect repellent
Keeps mosquitoes and ticks at bay, especially near marshes.
spring|summer|fall
Water bottle
Stay hydrated during the walk, particularly in warmer months.
Sun protection (hat, sunscreen)
Shield yourself from direct sun on open trail stretches.
spring|summer|fall