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“The driver was a 10 … the best. I have been a customer with you guys for 16 years. Teddy’s continues to set the bar in my mind for how it should all work. ”

Awards & Recognition

2023 ‘best car service’ by westport, weston & wilton magazine

Established in Westport in 1932, as Teddy’s Taxi, today’s Teddy’s Transportation System is proud to have been named the 2023 Best Driver Service of Westport, Weston & Wilton magazine. Teddy’s has been offering professional, safe and reliable, private car services to our busiest neighbors for 91 years!


 LCT Magazine 2020 Operator of the Year (31-44 vehicles) – Winner!

2020 LCT Operator of the YearLuxury Coach & Transportation Magazine has been the top trade media brand for the chauffeured transportation industry for more than 30 years, reaching thousands of industry leaders with its print and online media. Each year, Luxury Coach & Transportation Magazine awards the best players in the luxury coach and transportation business for their high standards, best practices and stellar performance. In the 31–44 vehicle category (operators with a fleet of 31-44 vehicles), Teddy’s Transportation System won Luxury Coach & Transportation Operator of the Year, beating out an array of other very impressive contenders to come out on top as the best in the biz for an operation with such a large fleet size.


LCT Magazine 2012 Operator of the Year (31-50 vehicles) – Winner!

2012 Operator of the YearLCT Magazine’s Operator of the Year Award is the most prestigious in the industry. The Operator of the Year Award honors chauffeured transportation operators in the $9 billion U.S. industry who have excelled in management, customer service, marketing, fleet quality, safety, and community and industry contributions. Peer recognition of unique abilities and accomplishments also is an important factor. A panel of professional judges score and select winners. Teddy’s Transportation System, Inc. was chosen as the 2012 Operator of the Year Award in the 31-50 vehicles category, and was previously named as one of three Finalists for the award in 2011.


Inc. 5000 Fastest Growing Companies For 7 Years in a Row!

Inc 5000 Growing Company AwardTeddy’s Transportation System, Inc., a global ground transportation company based in Norwalk, CT, was named to the Inc. magazine inaugural list of the 5000 fastest-growing private companies in the country and was a repeat selection for each of the next six years. Teddy’s was the only chauffeured ground transportation company in Connecticut and the Tri-state region to make the 2013 list. According to Inc. magazine, the annual list is the most comprehensive look at the most important segment of the economy: America’s independent-minded entrepreneurs.


Limo Digest Operator of the Year Finalist

Limo Digest Teddy’s Transportation System, Inc. was chosen as one of three Finalists in the large fleet category for the Limo Digest magazine Operator of the Year.



Connecticut Family Business of the Year Finalist

UConn Family Business The University of Connecticut Family Business Program named Teddy’s Transportation System, Inc. a Family Business of the Year Finalist . Teddy’s was one of four Fairfield County family businesses to receive the annual award.