EVENTS near the Glacial Drumlin Trail

Waukesha Night Out

Frame Park 1150 Baxter Street, Waukesha, WI, United States

Enjoy a night of safety information, public safety vehicle displays, games, and activities for all ages! You will also have the opportunity to meet some of the members of our Police Department, Fire Department and other public safety professionals. There will be food trucks at the event for food and beverage purchases

Country Christmas Light Show, Waukesha

The Ingleside Hotel 2810 Golf Road, Pewaukee, WI

Celebrating its 28th year, Country Christmas features over a million holiday lights festively displayed on 40 wooded acres of Waukesha’s countryside. Experience enchanting animated figures and holiday scenes all from the comfort of your car. $25 per carload or minivan, Sunday-Thursday $35 per carload or minivan, Friday, Saturday and Holidays

$25 – $35

Waukesha JanBoree, Waukesha

Celebrating the JanBoree’s 39th anniversary! Get out and embrace winter in Wisconsin. Fun for the whole family throughout Waukesha! Times vary based on event(s).

Wild Winter Night Candlelight Hike, Waukesha

Retzer Nature Center S14 W28167 Madison Street, Waukesha, WI, United States

Come explore the winding trails and quiet woods of Retzer Nature Center by candlelight on a self-guided hike. Snowshoes will be available if conditions allow.

FREE

Get Lucky Art Crawl, Waukesha

Downtown Waukesha Riverfront Street, Waukesha, WI, United States

Hundreds of artisans at 20 galleries and showplaces are featured at this seasonal event, walk the downtown streets to discover your next artistic treasure, shop the boutiques, listen to live music or indulge in food and drink.

FREE

Trailbreaker – 5k, 10k, Half Marathon, Marathon; April 7

Schuetze Recreation Center 1120 Baxter Street, Waukesha, WI, United States

The Trailbreaker is Waukesha's home grown running event and has been held annually since 1993. Since 2009, the Park Foundation of Waukesha, Inc. (PFW Inc.), has organized and hosted this annual event as a fundraiser for the enhancement of city parks, trails, recreation programs and the urban forest.

$5 – $60

UPAF Ride for the Arts

Henry Maier Festival Park 200 N Harbor Dr, Milwaukee, WI, United States

We are Riding for the Arts! The UPAF Ride for the Arts, Presented by Miller Lite, is more than just a ride – it’s an opportunity for friends, families and coworkers to have fun and support our region’s world class performing arts organizations. Bike the Hoan and support the arts on the 20-mile Hoan Loop...

$35 – $65

“Mother of All Crawls” Art Crawl, Waukesha August

Downtown Waukesha Riverfront Street, Waukesha, WI, United States

Hundreds of artisans at 20 galleries and showplaces are featured at this seasonal event, walk the downtown streets to discover your next artistic treasure, shop the boutiques, listen to live music or indulge in food and drink.

FREE

Riverside Rhythms, Waukesha

Downtown Waukesha Riverfront Street, Waukesha, WI, United States

Enjoy live music and tasty food over the lunch hour, while taking in great views of the Fox River in Downtown Waukesha during the summer!

FREE

“Mother of All Crawls” Art Crawl, Waukesha, December

Downtown Waukesha Riverfront Street, Waukesha, WI, United States

Hundreds of artisans at 20 galleries and showplaces are featured at this seasonal event, walk the downtown streets to discover your next artistic treasure, shop the boutiques, listen to live music or indulge in food and drink.

FREE

Event

Have an upcoming event near the Glacial Drumlin Trail you’d like to see featured here? Let us know and we’ll try to include it!