Freehold's first Harvest Festival was held the second tenday of Nightal, 1373DR, to celebrate the successful harvest of the first "real," organized community crops (wheat and corn planted earlier that year). Though it had been suggested prior, and was already in tentative planning stages before the event, the Harvest Festival also became a celebration of Freehold's victory in the recent Ghauwffhwar siege—a way to raise morale and boost spirits following the tragic surprise attack, as well as a memorial service for those defenders who lost their lives to the gnoll assailants.

The Harvest Festival met significant challenges early on, as Freehold faced numerous other issues at the time it was proposed, including questions of defense and debates over government. Councilor Vio Belc did his best to support and organize the celebration in the face of growing concerns over security and the announcement by fellow Councilor Shara Graye that stockpiled resources were slowly declining, but it would not have been possible without assistance from the community; a loose committee was formed to work on the event, which was supported by a generous donation from the House of Lazard to supplement the purchase of fanciful decorations and supply fresh beef and drink for the whole village.

This initial Harvest Festival was considered largely to be a success, encompassing an apprenticeship showcase, a small magefair, and variety of games and contests over the course of the tenday and concluding with a feast featuring music, singing, dancing, storytelling, and fireworks provided by local spellcasters, as well as inexpensive but clever magical decorations. Activities and competition winners are listed below:

Archery Competition:
1373DR: Samuel Fisher

Baking Competition:
1373DR: Lysander Arkaine

Footrace:
1373DR: Samuel Fisher

Horseshoes:
1373DR: Farwen Athscar and Dimble Garrick

Keg Toss:
1373DR: Samuel Fisher

Pie-Eating Contest:
1373DR: Samuel Fisher

Riddle Competition:
1373DR: Trendal Kingshand

Scavenger Hunt:
1373DR: Trendal Kingshand

Swimming Competition:
1373DR: Lysander Arkaine

Trial-by-Arms:
1373DR: Adoward Beastfriend

Wrestling Competition:
1373DR: Samuel Fisher

The Harvest Festival was meant to be the establishment of an annual tradition for Freehold, occurring on the same dates every subsequent year to celebrate the frontier settlement's continued success. Tentative long-range plans put the second Harvest Festival in Nightal, 1374DR.