Transportation methods and means has fundamental  shaped the places, people and environment of Chesapeake Crossroads. Long before European arrival, Indigenous peoples traveled natural paths and waterways throughout the region, creating routes that later influenced colonial roads and connected communities. Over time, those pathways evolved into stage roads, turnpikes, rail lines, highways, and recreational trails. Dozens of old, winding roads still evoke a time when travel was slower—and much more difficult.

In 2027, we invite heritage partners to bring this history to life and get visitors “On the Move.” Invite them to explore the Crossroads by land and water—from sailing vessels and steamboats to horses and carriages, railroads, historic roads, scenic byways, and trails.

Discover the railroad stories that shaped Maryland, from the Baltimore & Ohio Railroad and Odenton’s historic junction to the Baltimore & Annapolis Electric Railroad, whose former right-of-way now carries travelers along the B&A Trail.

Transportation stories continue into the automobile age, from historic and scenic roads to Defense Highway, the Blue Star Memorial Highway, and the Chesapeake Bay Bridge. Today, bicycle routes and the East Coast Greenway offer new ways to experience these historic corridors.

Your event might recreate a historic journey, explore a transportation corridor, feature a vintage vehicle or vessel, offer a guided walk or bike ride, or uncover the stories of those who traveled these routes.

Give visitors a reason to hit the road, follow the tracks, take to the water, or set out on a trail. Be creative, be evocative, and let’s get visitors moving through the Crossroads in 2027!