Find Things to do in Lake Country and Waukesha County with Kids this Day weekend!
May 29-31, 2026
Welcome to the Weekend Guide from Lake Country Family Fun – find our top picks for things to do this weekend, a link to the full events calendar, the weather for your outdoor weekend fun, and our local sponsors that keep the lights on here so we can keep bringing you the best local family fun and you can keep making fun memories with your family!
Be sure to tag us in your fun on social @lakecountryfamilyfun on IG.
This post contains affiliate links from Amazon. Lake Country Family Fun is an Amazon associate and earns from qualifying purchases at no extra cost to you. Thank you for supporting our small business!
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TAP HERE FOR THE FULL CALENDAR.
*Lake Country Family Fun Partner event. By attending and supporting Lake Country Family Fun partners, you support two local community businesses at once! Be sure to tell your friends, neighbors and the event organizers when there, that you saw their event on Lake Country Family Fun! We appreciate you!
*Jurassic Journey Waukesha
ALL WEEKEND: FINAL WEEKEND (we mean it this time)
Jurassic Journey Waukesha is presented by Empire Home Remodeling from May 28 – 31, 2026 at the
Waukesha County Expo Center.
*Okauchee Lions Days
ALL WEEKEND
Held at Okauchee Lions Park. Live Music. Local Food. Carnival and MORE!
Food Truck Friday at the Waukesha Airport
FRIDAY
Held at the Waukesha County Airport
*Head to a Farmers Market
SATURDAY + SUNDAY
We went to the Oconomowoc Farmers Market in the Bank Five Nine parking lot on May 1 and it was just what my soul needed, sun on my face and so many familar faces again after a long winter!
Held at various locations throughout Waukesha County; tap the image to find the list of farmers markets this weekend!
Bands at the Beach
FRIDAY
Held at City Beach in downtown Oconomowoc. First of the season!
Moms Mental Health Initiative Summer Social
SATURDAY
Held at Wilson Park Tot Lot in Milwaukee
Goat Yoga at Old World Wisconsin
SATURDAY
Held at Old World Wisconsin in Eagle, WI
*Pewaukee Lake Sailing School Grand Opening and Ribbon Cutting
SATURDAY
Held at the new Pewaukee Lake Sailing School
See them in our Summer Camp Guide!
*Maravilla Montessori School Open House 2026
SATURDAY
Held at Maravilla Montessori School in Waukesha
Get Some Ice Cream!
ALL WEEKEND
Try one of these 20 ice cream shops now open for the 2026 season! It's going to hit 80 again on Monday! Time for a sweet treat!
Find a Rummage Sale
ALL WEEKEND
Tap the image for the full guide. Find the Trinity Waukesha Lutheran Rummage and the Lake Country Village & Eastlake Village Neighborhood (Pabst Farms in Oconomowoc) and more!
Find a Splash Pad
ALL WEEKEND
Tap the image to find a splash pad - most of our 7 favorite splash pads open this weekend!!
Visit a New to You Park!
ALL WEEKEND
Tap the image to find your new favorite!
Try a New Gym of Fitness Class
ALL WEEKEND
Tap the image to find your new favorite!
We have intro deals from Oconomowoc Burn Boot Camp and 8th State Hot Yoga + Fitness and CMB Fitness in Pewaukee through the link!
Try a Date Night!
ALL WEEKEND
Tap the image for our updated summer date night guide!
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Tap the ad to learn more!
THURSDAY:
Sunny, with a high near 75. East wind 5 to 10 mph.
FRIDAY:
Sunny, with a high near 82. Calm wind becoming northwest around 5 mph.
SATURDAY:
Sunny, with a high near 79. Light northeast wind becoming east 5 to 10 mph in the morning.
SUNDAY:
Sunny, with a high near 77.
*from weather.gov for 53066 on 5/26/2026
Amazon Affiliate Link: Our favorite paper planner. I’m on my 5th year and gifted one to all my team members!!
Bloom Physical Therapy & Wellness offers expert, one-on-one pelvic floor physical therapy at their clinic in downtown Hartland, along with providing in-home treatment throughout Southeast Wisconsin. The physical therapists at Bloom offer care for women’s health conditions throughout the lifespan, including pregnancy care, postpartum rehab and birth doula services.
Learn more about them in our Moms Groups and Play Groups Guide.
Seasonal Guides to Skim:
Find the Best Fish Fry in the Area!
Tap for details and to see who won the best fish on 2026!
Find the Most Tried and True Baby Gear
Tap the image for the full list compiled by our friends at Moreland OB-GYN.
Free Summer Fun Guide
Find ideas for a FREE summer!
🛍️ Family Favorites We Use (Affiliate Links)
This section contains Amazon affiliate links. As an Amazon Associate, we earn from qualifying purchases at no extra cost to you.
Amazon Affiliate Links:
- A popular pick for toddler rain boots that our team uses for the rainy weather.
- A popular pick for luggage that our team uses for getaways.
- A popular pick for a handheld vacuum for cleaning up kid messes on the go.
- Our favorite scooter. We have two and the kids have been using them for years! We take them on trips, too!
- In 2025, my youngest got this scooter and now that is her favorite to ride around on at home.
- A popular pick for a door organizer for the mudroom/coat closet that Stephanie uses in her home. Every family member gets a labeled pocket for their outdoor gear, sunglasses, etc…
- A popular pick for a tumbler for coffee on the go.
LCFF FACEBOOK POSTS OF THE WEEK
CHECK OUT OUR GUIDES AND LATEST NEWS!
We’ve been busy over at Lake Country Family Fun working on these 7 latest projects/guides:
Waukesha County Fitness Guide
Want to join a gym? Boutique studio? Find one here! FREE Camps this week May 5-9 for Teacher Appreciation week at Burn Boot Camp Oconomowoc!
Lake Country Photography Guide
Need a local photographer? These are tried and true!
Grocery Delivery and Pick Up Options
NEWLY Updated Make every day easy with grocery pickup and delivery. Great options in our area.
Lake Country Coffee Shop Guide
Warm up this spring! Find a locally owned coffee shop throughout the Lake Country area.
Playgroups and Mom Groups Guide
Are you looking for moms groups or other moms to meet up with and playgroups to join with children the same age as your children? We have compiled a list of moms groups in the area.
Waukesha County Preschool Guide
Find 30+ Local Preschools Find which local preschool is the best fit for your family!
Birthday Party Guide
Find 50+ Local Birthday Venues + Local Businesses Celebrate your little one or yourself with one of these fun ideas!
See what people are saying about us…
Thanks for sharing! I have off this Friday and wanted to do something fun with my kids. I think we’ll check out the Food Trucks and then the drive-in concrete at night with my husband. I’ve seen a lot of friends going to drive-in concerts and I’ve wanted to go to one too, so this works out perfectly. Thanks again!
You’re welcome! We really enjoyed the Food Truck at the airport to watch the planes. Do plan extra time in case there is a line for food. Enjoy the concert as well!
I have heard about the Brookfields Farmers Market but never made it out. I think my kids would love it! I remember my first bartering lessons were at the swap meet!
Farmers markets are amazing for kids! It’s a great way to see and buy homemade, fresh local produce and products.
Thank you so much for the sledding hill guide and map! I’m afraid the kids have been getting incredibly restless lately now that the holidays are over and along with the pandemic. Could use some good sledding time to get it out of their system!
You are very welcome. We loved putting it together.