Things To Do

Things To Do > Explore a Water Trail

The Chesapeake region offers a wealth of natural, cultural and historic places to visit, many of which Captain John Smith explored and mapped for the first time during his 1607-1609 voyages. His amazing journeys are being honored and interpreted through the Captain John Smith Chesapeake Trail, which includes more than 60 sites throughout the Chesapeake region. But with all those trail sites, it may be hard to choose which one to visit!

To get you started on a great Chesapeake experience, our trail experts have developed several pre-planned itineraries that will help you get the most out of your trip.

Each trail exploration itinerary includes:

  • The types of activities offered at the site, such as hiking, biking, swimming or bird-watching.
  • A description of the site’s scenery and trail offerings.
  • Optional side trips you can take if you decide to extend your stay in the Chesapeake region!

Each itinerary also contains information about Captain John Smith’s visit to the site during his two Chesapeake voyages. After learning about Smith’s encounter with the site more than 400 years ago, you can retrace his path on your own modern-day exploration.

Interactive Content

For Boaters

Boaters Guide

Download the official Boater's Guide.

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Smart Buoys

Smart Buoys

Learn about buoys marking the trail.

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Chesapeake Explorer app

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My Adventure Planner

Boat Wheel

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