Find Things to do in Lake Country and Waukesha County with Kids this weekend!
May 15-17, 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!
Want all the weekend fun sent directly to your inbox? Join our Enewsletter so you never miss out on the fun!
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
Jurassic Journey Waukesha is presented by Empire Home Remodeling from May 8 – 25, 2026 at the
Waukesha County Expo Center.
*DelaSPRING
SATURDAY
Held in downtown Delafield. Don't miss this family favorite spring festival! We went last year and had a blast.
*Head to a Farmers Market
SATURDAY
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!
*Block Party at Next Gens Academy
SATURDAY
Held at Next Gens Academy in Pewaukee/Waukesha. I toured the campus and between the building and the outside space, it's gorgeous!
*Mindful Me: Mental Health Resource Fair
SATURDAY
Held outside Birch and Banyan in downtown Hartland. We went last year and met so many amazing people!
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 this weekend! Time for a sweet treat!
*Splatter Fest – A community fund raising event for NAMI (Held at the Mindful Me Mental Health fair)
SATURDAY
Held outside Birch and Banyan in downtown Hartland as part of the bigger Mindful Me Event. *Fee associated as it is a fundraiser.
Find a Rummage Sale
SATURDAY
Check out some rummage sales and the Okauchee Lions Super Flea Market!
Free Craft & Open House at Stonecutter Arts
SATURDAY + SUNDAY
Held at Stonecutter Arts in downtown Oconomowoc. We went opening day on May 1 and it's so cute! You must check out this FREE event 🙂
Mukwonago Book Festival
SUNDAY
Held at the Mukwonago Community Library
Find a Rummage Sale
ALL WEEKEND
Tap the image for the full guide. Find the an estate sale and a FREE Book Fair in Hartland!
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!
Since 2015, Caitlin Dennis has operated on a simple premise: real estate is a deeply human experience, not just a financial transaction. While her track record includes more than $140 million in career sales and over 350 closed transactions, her true measure of success is the peace of mind clients feel from start to finish.
Caitlin Dennis brings a high-energy, all-in approach to every interaction, taking each client’s goals personally. To her, clients are never just transactions, they are relationships built on trust. Through both the high points and the hurdles, she remains a constant advocate, handling the heavy lifting and complex negotiations behind the scenes to ensure a clear, calm, and seamless experience.
Her commitment to the industry is reflected in strong results, including a career high of $18.8 million in sales in 2025. These milestones are driven by long-term relationships, built on attentive service and the belief that every client deserves an expert who genuinely cares about their outcome.
Tap the ad to learn more!
THURSDAY:
Sunny, with a high near 68. Calm wind becoming south around 5 mph in the afternoon.
FRIDAY:
A chance of showers, with thunderstorms also possible after 1pm. Partly sunny, with a high near 75. Chance of precipitation is 50%.
SATURDAY:
A 20 percent chance of showers and thunderstorms. Mostly sunny, with a high near 78.
SUNDAY:
A 40 percent chance of showers. Partly sunny, with a high near 80.
*from weather.gov for 53066 on 5/11/2026
Amazon Affiliate Link: Our favorite paper planner. I’m on my 5th year and gifted one to all my team members!!
SpeechWorks LLC
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.
Date Night Guide
Find ideas for a unique date night!
🛍️ 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.