Smilin' Jake's Casual Apparel

Need a taste of the islands from time to time? Whether Hawaii or the Caribbean ... a laid back place with palm trees, sandy beaches and the sounds of island music drifting on warm breezes. Smilin' Jake's, on the eastern shore of the Chesapeake Bay in Rock Hall, Maryland, is the store for you. We can’t wisk you away to the tropics, but for the past 20 years our casual tropical apparel has helped many to relax, live the tropical fantasy and forget about rush hour traffic for a bit ...

Tuesday, January 2, 2018

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Happy New Year and welcome to 2018. Just thought this might be appropriate since most of the country is a deep freeze for a while. Put on yo...
Tuesday, December 12, 2017

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Smilin' Jake's Casual Apparel NEW E-Commerce web store address www.smilinjakescasualapparel.com

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Almost time for Merry Christmas from us to you but.... not just yet For all those that have been saying for years tha...
Friday, November 10, 2017

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Smilin' Jake's Casual Apparel New Store 5770 Main Street, Rock Hall 21661 Aloha to all. It has been way to long since my la...
Thursday, August 24, 2017

July Cruise Night 2017

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Wednesday, June 28, 2017

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The BIG TWO "O" That's right this is Smilin' Jake's 20th. year in business. Thanks to you are customers. Our than...
Tuesday, February 7, 2017

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We are back,           2016 is behind us and time for a new year. For those who follow the groundhog, for get it is prediction is just s...
Thursday, December 1, 2016

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Thursday, December 31, 2015

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Aloha and Welcome                    to the a New Year
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Wednesday, August 5, 2015

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Available in 3 sizes Small: $155 Medium: $175 Large: $175 The History behind CHART metalworks Chart metalwor...
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About Me

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Smilin' Jake's
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”.

With cars being a long lost passion I thought maybe I could get back in some small way. It has been a long time since my last show car.... I decided to do the next best thing and that was to help organize a "Cruise Night" here in Rock Hall, Md.

The hope is to have some fun, meet some new freinds and bring together what Rock Hall has to offer with what the "Cruisers" can bring to our great town.

Mahalo
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