In 1994 The Orleans Farmers' Market started with a handful of vendors in the parking lot of the Orleans Bowling Alley.
In 1995 the market moved to The Cape Cod Five Operations Center on West Road. The market grew to about 15 vendors and stayed at C.C.5 until 2000, opperating from June to September.
In 2001 the market moved to 21 Old Colony Way.
In 2003 The Orleans Farmers' Market, Inc. became a Massachusetts non-profit and grew again to 30 vendors and operated from May to November.
From 2012 to 2014 a Wednesday afternoon market was added during July and August. The Wednesday market was discontinued in 2015 due to lack of customers.
In 2014 the Community Development Partnership received a grant to pilot an every-other week winter market. The market ran from December to April during 2014-2015 and 2015-2016.
In 2016 The Orleans Farmers' Market, Inc. applied for Non-Profit Status with the IRS.
In December 2016 and running to April 2017, the market has been run as a weekly winter market collaboration between the CDP and The Orleans Farmers' Market, Inc.. The market has an average of 22 winter vendors each week.
In 2018 the Orleans Farmers' Market, Inc. will be a year-round market, running from January to December and open for 50 weeks.