Explore

Unwind

Reconnect

Guided by Local Knowledge Since 1999

Chester River Kayak Adventures is owned and operated by Jim Gillin, who has spent more than 20 years paddling the local creeks, coves, and waterways of Maryland's Eastern Shore. Before launching the company, he operated a paddlesports retail shop on Main Street in Rock Hall, bringing years of hands-on experience and local knowledge to every adventure.


Whether you're planning a half-day outing or a week-long exploration, we're here to help you find the right equipment, route, and experience for your time on the water.

  • Maryland State Business License
Choose the adventure that fits you best

Kayaks

Stable singles, tandems, triples, and fishing kayaks, matched to your comfort level.


Paddleboards

Inflatable, beginner, and performance boards for fun workouts on calm tidal creeks.


Discover Our Story

Since 1999, we have shared local creeks, simple gear, and relaxed guidance that help you enjoy nature safely and comfortably on your own self paced paddle.