Sookie and Lorelai first discover the inn through Luke's ex-girlfriend, Rachel. Rachel is a photographer and finds the disheveled Dragonfly Inn and showed Lorelai the pictures, sparking her interest in the old building.
The inn was a pre-existing inn owned and run by the family of Fran Weston, that had fallen into disrepair. Fran initially refuses to sell the place, but not long after dies and with no inheriting family members, Lorelai and Sookie negotiate a deal at Fran's funeral with the family attorney.
At first, Lorelai thinks she cannot buy the Dragonfly because she has to pay for Rory's Yale tuition. However, when Rory approaches Richard and Emily for the money for Yale, Lorelai asks Luke for a $30,000 loan and renovation on the Inn begins. Tom is hired as the contractor, and soon the Dragonfly Inn is ready to open.
Before they open up to customers, Lorelai, Sookie and Michel host a test run when they invite their friends and Lorelai's parents. Having been successful, the Dragonfly Inn finally opens to the public.
After balancing their costs at one year into the run, Richard Gilmore, through business contacts, gets an offer from Mike Armstrong, owner of the Durham Group, who buy boutique inns and woo Lorelai and Sookie. While Richard remarks that they retain the management, Lorelai seems happy to stay where she is, although she would become an international consultant and finally get to travel the world on business.
- Originally also known as The Violet Lady
- The Dragonfly has two horses – Cletus and Desdemona
- The Inn was located on 3rd Street before the street names were changed in Stars Hollow, after the street was called Sores and Boils Alley. According to a letter written by Lorelai to Rory on Dragonfly Inn stationary (on display at the Warner Brothers Studio tour in Burbank, CA), the address finally became 214 Oak Tree Lane, Star Hollow, CT, 06109. Tel: 203.555.0106. Fax: 203.555.0112.
- It was first seen when Rachel takes Lorelai there to take pictures.
- The house used for the inn was the Walton's family home in The Waltons.