Best date locations + Ideas in lake country and Waukesha county
When was the last time you went on a date or a group couples date? It’s been a while for us, but it’s definitely on our radar. However, when a date night does pop up, we usually spend too much time planning out what to do and where to go. Whether you are kid-free or have a babysitter for a night, we’ve got a great date list for you that will have you spending less time figuring out what to do and more time enjoying it!
Below you will find a categorized, all-season, date list for you and your loved one or even a group of friends. So book that babysitter, make those plans and enjoy some date night out fun.
Categories in this guide include:
- Milwaukee Improv – top date night recommendation
- On the Lake Dining Spots
- Best Patios (non lakefront)
- Best Burger Spots
- Best Hikes and Trails
- Seasonal Staples – Summer & Fall Ideas
- 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.
See comedy show at the Milwaukee IMPROV for an awesome date night:
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 2023. There are over 25 lakefront dining locations!!!
*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 2023. 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 Bar 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
- Neighbors in Waukesha
- 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
- Make it a date night at American Family Field to see the Brewers
- Go STRAWBERRY PICKING with your date.
- Catch an OUTDOOR MOVIE
- Every good date ends with an Ice Cream Cone – check out 20 PLACES to grab one in Lake Country.
- Rent a donut boat (or other types of boats) from BoatMKE.
- 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.
- Catch a movie at the DRIVE IN MOVIE theatre in Jefferson or other options.
FALL STAPLES
- Trot through a corn maze at night.
- Get spooked together at a local haunted house.
- Attend a local fall festival like a local Oktoberfest.
- Pick apples together and enjoy one of the many farms with other fun offerings like beer gardens.
- Go for a fall hike together on a local trail (pick up Mountain Top Coffee for your adventure).
TOTALLY UNIQUE IDEAS
- Rent a pedal boat on City Beach followed by a Martini on the Splash Martini Bar patio.
- Discover a new Brewery
- There are a few Golf Simulators around Lake Country, including a new one coming to Oconomowoc + XGolf at American Family Field in Milwaukee.
- Go Bowling
- Walk Downtown Oconomowoc or along Pewaukee Beach.
- Check out all the fun at WHIRLYBALL in Brookfield
- Group date on the Milwaukee Pedal Tavern from Vino Etcetera in Oconomowoc.
- Wine Tasting – Try Piper Porch in Mukwonago or the Eagle Public Market offers wine tasting nights
- Try out Life’s A Picnic – a Pop-Up Picnic Planner business! Find out more here.
- Catch a performance at Lake Country Playhouse.
- Couples Golf at the Club at Lac LaBelle or another course.
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!
Need a sitter?
Check out this guide for ideas on child care in Lake Country.
