Erin and Stephanie at the Pewaukee Wauesha airport for Positvely Pewaukee

All things Positive about Positively Pewaukee

Positively Pewaukee is an award winning non-profit known as being Lake Country‘s Premiere event source.  And in 2021 they celebrated 25 years! Tens of thousand attend Taste of Lake Country on the shores of Pewaukee Lake each July. In 2023, this popular event will be retiring, but there will be a new event for families to have fun in the summer! Wednesdays throughout the summer, many attend Waterfront Wednesdays, which is coming back in 2023!  But, did you know all the other things Positively Pewaukee does and is doing?  Erin and Stephanie (pictured above) sat down with Executive Director, Elaine Kroening, to talk about the Positive Things Positively Pewaukee does for our community.  Read on to be inspired! We sure were!

*This article was initially written in 2019. In 2023, Elaine Kroenig retired, and Liz Unruh has taken over to continue running Positively Pewaukee smoothly.

Did you know Positively Pewaukee has a YouTube Channel? It’s true!

Positively Pewaukee: What they are doing:

  • Producing events such as Taste of Lake Country (in the past) and Waterfront Wednesday concerts.
  • Providing financial and volunteer support through our Community Connection Committee.
  • Working with the Pewaukee Schools to provide backpacks for children in need and to provide help to families in financial crisis.
    • Plus check out The Reality Store at Pewaukee High School in spring.
  • Fostering business growth and promotion through our merchants’ group and one on one meetings with downtown merchants.
  • Beautifying our downtown through our gardening and streetscape projects

All this with only 1 paid staff and over 200 volunteers!

Let’s Break Positively Pewaukee Down:

Community Connection Program

Community Connection is a subcommittee of Positively Pewaukee that works with Pewaukee schools, churches and the food pantry to help people in crisis. They work with United Way’s Backpack Coalition to supply filled backpacks to children who need help this year providing 100’s of backpacks to our children.  They provide clothing items for children in need at school and work with the school councilors on other needs. They are funded through generous people who believe that our community should take care of its own. 

Merchant’s Group

Positively Pewaukee hosts meetings with all downtown and Capitol Drive merchants bringing in guest speakers, working on partnerships between the merchants and giving them updates on things happening in the Village.


Positively Pewaukee, with the help of many volunteers, plants and maintains the flower beds and flower pots in downtown Pewaukee.  For many years the flowers have been provided to the village free of charge from Schulte’s Microfarm Greenhouse and Fun Center in Pewaukee.  Numerous groups, individuals and families volunteer their time to weed, water and maintain the many flower beds and pots downtown.  If gardening is something that interests you, they are always looking for more helping hands! 

Positive Pewaukee Upcoming Events

Waterfront Wednesdays Summer 2023

  • Annual weekly concert series at Lakefront Park. Scheduled for June 7 – July 26th. Details and lineup HERE.

Summer Sizzle (In place of Taste of Lake Country)

  • NEW EVENT:  July 15th from Noon – 10:00pm
  • Food, RiverGlen Church Kids Area, Bocci Ball and Bags Tournaments and more!

Halloween Fun Fest – October 2023

  • Join one of our favorite annual events in Pewaukee: Halloween Fun Fest! 
  • Halloween Fun Fest will be held on October 2023 downtown Pewaukee with merchant Trick or Treating from noon – 1:30 pm. 
  • Please only visit merchants who have displayed a Trick or Treat sign in their business window.
  • The annual dog costume contest will be held in front of End of the Leash at noon.
  • Be sure to dress up, too!

Scarecrow Contest

Register by September 30th to receive a location!

  • Must be put out Oct 9-11.
  • Must be taken down by Nov 7th.

Positively Pewaukee – Holiday Online Shopping Fair Oct 24

  • October 24th, 2020 – 10:00 a.m. – 2:00 p.m.
  • Positively Pewaukee is excited to announce our first online sales fair that will feature high quality arts, crafts, and products on October 24th, 2020, from 10:00 a.m. – 2:00 p.m. We invite you to apply to be part of this unique and exciting event!
  • Our Holiday Online Shopping Fair will provide the opportunity for you, as a Vendor, to have real, live time, face-to-face interaction with customers without having the need to attend an in-person fair or man a physical sales booth. The Holiday Online Shopping Fair is a LIVE Virtual Event featuring an interactive page where customers can see multiple Vendors at a glance. In addition, each Vendor will be provided with an individual “tile booth” portal, similar to an on-site event.  Please click on the link for further details and to apply.  PP – DRAFT – VENDOR LETTER APPLICATION and AGREEMENT – sept 22

Gingerbread at the Police Station – Holiday

  • Check back closer to fall 2023 for more information on this favorite event.


It takes over 200 volunteer and 4,000 hours to help complete the mission of Positive Pewaukee each year. You can find out about all the ways you can donate your time here:

How to Volunteer

I think the most inspiring part of our meeting with Elaine of Positive Pewaukee (and getting to know her better throughout the years) is her true care for the people (and especially the kids) of the Pewaukee community. She beams with excitement telling us about a connection between a kid and a police officer through a program that she thinks has forever changed the kids life. She grins from ear to ear discussing how many kids received school supplies when it was identified out of a need. She continually pushes for a more positive world and has a great board of directors in the community also working towards those noteworthy and commendable goals. Go Positive Pewaukee! We love you!””

Stephanie Cutler

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