Who is Smilin Jake !!!
If you don’t already know us you might ask yourself just who or what is Smilin’ Jake’s.
As to the name “Smilin’ Jake’s” it was the name of my best friend Jacob Austin Kees Esquire or “Jake”. For you dog lovers,
Jake was as happy a Keeshond as you could ever find and he never went anywhere without his Hawaiian print scarf on and a great big smile for everyone he met, thus the name was born “Smilin’ Jake’s”.
It was my love of sailing that brought me to this town in the 80’s when I moved here to work for and now partner in Gratitude Yachting Center. As time would have it there was one thing that I missed and that was the feel of Hawaii and the tropics, so I thought about how could I bring what was missing to this great little town in a way that everyone could enjoy.
With surfing, sailing and cars being my passions, what goes better with all that than a whole lot of aloha shirts, some tropical music, a palm tree or two and a sandy beach? The sounds of Buffett, Don Ho, Iz and the Beach Boys are always in the air here and the fragrances of the tropics can never be missed.
Well, Smilin’ Jake’s is “just a state of mind”. We are that little displaced piece of island paradise tucked away in a small town on the eastern shore of the Chesapeake Bay. We opened our door (singular) in 1998 with a 160 square foot store (which many questioned my sanity, a Hawaiian shirt shop in a fishing village on the Chesapeake Bay). I guess it worked because the next move was to a slightly larger location on Main Street, which we continued to operate as a seasonal business 
until the spring of 2007. And then the big move! With a lot of help from my partner Linda and many friends we opened our doors (plural) on Memorial Day 2007. We opened our current location in a beautiful historic building on the corner of Main and Sharp streets but still in that great little fishing village of Rock Hall, Md.
The store became a year round business and now with the addition of this web site we will be now able to help our friends and customers when they are not able to be here. This town may not be on the Hawaiian Islands but it has more than its share of Aloha for the people that both live and visit here.
For those of you who have never been here, we hope you will visit our town and stop in and say Aloha.
Mahala
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