Old Settlers Day has been a Whitley County institution since 1904 when the first reunion of the pioneers was held at Loon Lake.

Whitley County residents and visitors of all ages are encouraged to come to the Whitley County Historical Museum Annex to register their attendance on Old Settlers Day. All ages are welcome and encouraged to register.

For over a century part of the Old Settlers Day celebration has been annually recognizing two honorary residents, the Longest Continuous Resident of Whitley County and the Oldest Registered resident of Whitley County. In years past those residents were presented with and engraved trophy, fondly called the “Loving Cups” for this distinguished milestone.

The presentation of these cups date as far back as 1904 and were very coveted amongst those who visited Old Settlers to record their name in their township of residence.

In more recent years the cups were discontinued and recipients were given an engraved plaque. A new tradition began in 2022 as those who achieve these still much coveted awards as the Longest Continuous Resident and the Oldest Resident will have their names engraved on a perpetual memorial plague that will be on display at the Whitley County Museum.