windorchid govcup2011

Galena bike ride

Gary Oster Fishing Trip




Steve MillerChesapeake Bay living means living life large, outside, on the water and on land. 

This section focuses on the Chesapeake Bay outdoor life: sailing, power boating, fishing — and eventually,  cycling, hunting and other outdoor activities. Our bloggers offer their insights.

Your response is welcome. Let’s get a conversation going!


Our Bloggers

The Captain’s b-Log

Jon Jones sailing Wind OrchidJon Jones is a veteran sailor of the Chesapeake Bay, but has often dipped his keel in the Pacific Northwest, British Virgin Islands and Jamaica. He sails The Wind Orchid, a Catalina 350. He’s a retired U.S. Army Captain who served as Commodore of the Canadian Forces Sailing Association. Jon holds the Canadian Yachting Association’s Intermediate Coastal Cruising certificate, the American Sailing Association’s Advanced Coastal Cruising certificate and is an ASA qualified sailing instructor. 
 Fishing Report

Gary Oster with RockfishGary Oster has been enjoying life on Chesapeake Bay for nearly 60 years.  He is an award winning photographer, a published freelance writer, a commercially rated 50 ton USCG captain and a SCUBA certified diver.  Living in Annapolis, he is an avid sport fisherman that loves casting, trolling or jigging for rockfish on the bay, chasing marlin offshore, flats fishing for barracuda in the Florida Keys or pulling in monster Halibut in Alaska.  A member of the Eastport Yacht Club he is ‘living the dream’ when he isn’t hard at work as an association executive in Washington DC.



Notes on Powerboating

Scott AndersonScott Anderson has been working in the marine industry in many capacities from charter fleet operations in the US and British Virgin Islands to managing full service marinas here on the Chesapeake Bay. Visit Scott at





Chesapeake Bay Cycling & Running

Owners of of TriCycle & Run, St. Michaels, MD

Laura (left), Jason (right) & professional triathlete Richie Cunningham (middle)

Jason and Laura Chance are married and own the TriCycle & Run cycling-shop (929 South Talbot Street) in St. Michaels, Maryland. Jason is an active triathlete and has competed in events all over the country. Laura enjoys bicycle riding on a more casual level, but has completed the Seagull Century, a 100 mile bicycle ride from Salisbury to the beach and back. They live in St. Michaels with their family and encourage their blog readers to stop by and say hello. Jason has recently been certified as a USA Triathlon Level 1 Coach!