Best date locations + Ideas in lake country and Waukesha county
Now that the weather allows for some outdoor fun, couples are getting excited to enjoy it with the special someone. Whether you are kid-free or have a babysitter for a night, we’ve got a great Summer Date list for you! Or, bring the kids to some of these great ideas. We’ve put together a categorized, summer-specific, date list for you and your loved ones. So book that babysitter, make those plans and enjoy this summer of love.
Categories in this guide include:
- On the Lake Dining
- Outdoor Dining/Patio Spots (non-Lake spots)
- Best Burger Spots
- Best Hikes and Trails
- Summer Staples + Unique Ideas
- Outdoor Beer Gardens
- Paddleboard/Kayak/Boat Rentals
Note: Reach out to individual businesses for hours, availability and pricing. Lake Country Family Fun is not responsible for availability and pricing of these events.
are you asking, where should we go on a date? We've got you covered!
ON THE LAKE DINING
You can view our Guide for Lakefront Dining here. It’s sponsored by the Delafield Brewhaus in 2021. There are over 25 lakefront dining locations!!! For sunset views, may we recommend Seven Seas in Hartland.
*FOR OUR GUIDE TO LAKEFRONT DINING CLICK HERE.
OUTDOOR DINING/PATIO SPOTS (NON-LAKE SPOTS)
You can view our Guide for Dining on the Best Local Patios here. It’s sponsored by the Delafield Brewhaus in 2021. There are nearly 50 awesome PATIOS listed!! For ample space, may we suggest the Delafield Brewhaus.
*FOR OUR GUIDE TO THE BEST PATIO DINING CLICK HERE.
BEST BURGER SPOTS (AS RECOMMENDED BY OUR FACEBOOK GROUP)
- Mainstream Bar & Grill in Waukesha
- Crafty Cow in Oconomowoc
- Joe Mamas in Colgate
- Sweet Dreams in Hartland
- Beer Snobs in Hartland
- Sobelemans in Waukesha
- Kick Switch in Okauchee
- Gina’s in Pewaukee
- David Alan Alan’s Smokehouse in Mukwonago
- Bass Bay Brewhouse in Muskego
- Sideliners in Genesee Depot
- Pointe Burger in Pewaukee
- Jake’s in Brookfield
- Stolley’s Hogg Alley in Oconomowoc
- Revere’s in Delafield
- Grill Junkies in Delafield
- AJ O’Brady’s in Menomonee Falls
- Foolery’s in Okauchee
- Most of THE ICE CREAM JOINTS make amazing burger spots too!
BEST HIKES AND TRAILS
- Nature Hill in Oconomowoc
- Cushing Memorial Park in Delafield
- Cushing Park Road Recrational Trail (LINK) – connect Glacial Drumlin and Lake Country trails
- Lapham Peak State Forest (LINK)
- Fowler Lake Loop
- Muskego Recreational Trail (LINK)
- Fox River Trail in Waukesha (LINK)
- All of the County Parks have hiking or trails:
- Retzer Nature Center in Waukesha
- Vernon Marsh
- Emma Carlin Trail in Eagle (LINK)
- Schuppernong Trail in Dousman (LINK)
- Ice Age Trail segments throughout our county (LINK)
FOR BIKING TRAILS, REFER TO OUR BIKING GUIDE TO WAUKESHA COUNTY 
*WATCH FOR TICKS! ALWAYS CHECK YOURSELF AND YOUR DATE OVER AFTER GOING ON A HIKE/BIKE RIDE.
SUMMER STAPLES
- Go STRAWBERRY PICKING with your date.
- Every good dates ends with an Ice Cream Cone – check out 18 PLACES to grab one in Lake Country.
- Some of these ideas in our 77 THINGS GUIDE, may spark an idea for a perfect date!
- Low budget? No problem! FREE SUMMER FUN GUIDE has you covered.
- Suntan and swim with your cutie on a LAKE COUNTRY BEACH. There are 12 to choose from!
- Shop together at a FARMER’S MARKET.
- Catch FIREWORKS with your sweetheart. Our anniversity is July 3rd so I say that there will always be fireworks.
- Catch a movie at the DRIVE IN MOVIE theatre in Jefferson or other options.
- Hit the links and try golfing! View the Golf Guide for courses and mini-golf ideas.
- Enjoy a night at an outdoor beer garden, even one with music! (See below for list of beer gardens in 2021.)
TOTALLY UNIQUE IDEAS
- Rent a pedal boat on City Beach followed by a Martinia on the Splash Martini Bar patio.
- Group date on the Milwaukee Pedal Tavern from Vino Etcetera.
- Try out Life’s A Picnic – a Pop-Up Picnic Planner business! Find out more here.
- Catch an outdoor play with the Summer Stage season 2021 at Lapham Peak.
- Couples Golf & Friday night fish fry at Western Lakes Golf Club!
OUTDOOR BEER GARDENS
- Raised Grain Brewery and Waukesha County Parks Pop-Up Beer Gardens
- The Beer Garden at Menomonee Falls
- The BEERGO with multiple dates + locations
- Beer Garden at Nixon Park Hartland
- more…
*To find out more details about each of these beer garden, go to our BEER GARDEN GUIDE! Many of them include entertainment for your date!
Going on an active date is an awesome idea. There are so many lakes in the area to utilize for this active fun! Enjoy a day on Lac La Belle on a luxury pontoon boat… tubing and lily pads available to rent too from laclabelleboats.com. Another idea for active fun is couples golf and Friday night fish fry at Western Lakes Golf Club!
Check out the Kayaking Around Lake Country Guide for:
- List of Rental Locations (including our Kayak Guide sponsor, Pato Loco Rentals who deliver within 15 miles of Delafield)
- Where to Kayak: Lakes & Rivers
- Recommendations from Fans
- Weather Report
Enjoy your date!
77 Things to Do this Summer in Lake Country
It's our summer bucket list in conjunction with the Free Summer Fun guide. We have 77 things to do with your family this summer in the Lake Country area and beyond so you never hear the words "I'm bored!" 🤩 This guide is made possible through our partnership with Postively Pewaukee presenting Taste of Lake Country and Waterfront Wednesdays.
Need a sitter?
Check out this guide for ideas on child care in Lake Country.
