Tookish Travelers

The Tookish Travelers represent the companions of those that went with Belladonna Took and her brother Hildifons Took on an adventure with Gandalf. Though Hildifons never returned, Belladonna managed to gain a sizable fortune which allowed her good economic standing among the Hobbits of the Shire. Her home of Bag End would eventually be passed down to her son, Bilbo.

Whatever happened during her and Hildifons's adventure, it is assured that she made her fortune at this adventure and that Hildifons disappeared.

Given the dates of when she was young, and before she had Bilbo, and the likely scenario that fits into the timeline of Professor J.R.R. Tolkien's writings of the Hobbit and Lord of the Rings the following adventure seems to make the most sense and fits perfectly in the timeline:

After Gandalf discovered Thrain and the loss of Durin's Ring, Gandalf went on an adventure to try and recover the items of Durin in Moria in order to rouse the Dwarfs to action in retaking Erebor, and uniting against the Dark Lord.

In T.A. 2883, these individuals are who went with Gandalf on his adventure to secure the lost items of Durin:
 * Gandalf
 * Hildifons
 * Belladonna
 * Elladan
 * Elrohir
 * Gwaewar (Great Eagle), Gandalf heals and he helps Gandalf’s party fly back to safety.