Giving Tuesday @ WinMan

Giving Tuesday 2021 – WinMan Trails


What if your organization has never done a Giving Tuesday campaign before? Where do you start?

The operations director at WinMan Trails, a 501(c)3 nonprofit trail system in northern Wisconsin, called Lemon Zest Copywriting with exactly that challenge. The organization had built up an email list of 1,000 and a very engaged Instagram audience, but they hadn’t done a formal fundraising campaign before. Giving Tuesday seemed like a great way to start.

In addition, previous conversations and interviews with users and community members had revealed some people believed the land and trails were owned/maintained either by the town or by a private landowner. We wondered if these misconceptions might hinder donors from making a gift.


Together, we decided on a mix of Email and Instagram messages that highlighted the incredible user experience as well as the family- and dog-friendliness of the facility and trails. We included an educational component letting supporters know that the WinMan Trails organization was completely supported by donations.

WinMan Trails had secured a sponsor for a matching gift challenge, which was an important part of the success of the campaign.

Since we had no data to help us predict how much this campaign might raise, the internal goal was to raise $5,000 from the community in order to max out the $10,000 we had in pre-solicited, double-match funds. When the dust settled at the end of the week, WinMan Trails had raised nearly $15,000 from the community, 3x what we had hoped!

See the progression of messages sent between November 29 and December 1, 2021: