Fun and Romantic Date Night Ideas for Couples

Here’s a list of fun and romantic activities for couples in the Milwaukee, Waukesha and Washington County, WI area — perfect for date nights, pre-wedding getaways, or just enjoying time together. This list blends adventure, relaxation, creativity, and a touch of wine:

1. Winery & Tasting Experiences

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  • Cedar Creek Winery (Cedarburg) – Tour the wine cellar in a charming historic mill and enjoy a romantic stroll downtown Cedarburg afterward.https://cedarcreekwinery.com/

    Cedar Creek Winery - Cedar Creek Winery

    CEDAR CREEK WINERY Open Daily 10am - 5pm, Fridays & Saturdays. Open until 6pm Curbside pick-up available 11am-4:30pm.



  • Vines to Cellar (Port Washington) – A small-batch winery where you can even bottle your own wine. www.vinestocellar.com

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2. Lakefront Brewery Tour

A Milwaukee must-do! This hilarious and interactive brewery tour includes samples, local lore, and views of the riverwalk. Sit outside afterward for cheese curds, beer, and river views. Www.lakefrontbrewery.com 

Lakefront Brewery | Born in Riverwest Raised all over

Since 1987, Lakefront Brewery has brewed Milwaukee's best beers, including Riverwest Stein, New Grist, and countless other innovative and imaginative craft brews.

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3. Wisconsin Boot Kickers (Line Dancing Group) https://wisconsinbootkickers.com/

CONTACT

Sept 3, 10, 17, 24 Wednesday 6:15-7:15pm Beginner Lessons Bubs Germantown+ Sept 3, 10, 17, 24 Wednesday 7:30-8:30pm Improver Lessons Bubs Germantown+ +Includes Practice Time - Open Dance Time - All Lesson Step Sheets (Registration starts in August)

  • What it is: A friendly, welcoming group teaching line dancing—country, pop, and more—for all levels. Expect fun classes, monthly workshops, free open dances, and themed events around Southeastern WisconsinEventbrite+12Eventbrite+12TravelWisconsin+12.

  • Typical events:

  • Why it’s great for couples:

    • Learn something new together in a lively, social setting 

    • Casual and low-stress—many events are free or low-cost

    • Delicious local food and drinks available at venues like Bub’s and Harvest & Vine

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4. Holy Hill Art Farm (Hubertus, ~30 min from Milwaukee)

  • Overview: A 165-year-old family farm turned into a creative oasis. Thoughtful rustic charm meets artistic meaningFacebookAllEventsEventbrite+2Eventbrite+2Eventbrite+2 www.holyhillartfarm.com 

    Holy Hill Art Farm | Event Venue & Farm | Wisconsin

    Originally our Loosen Family Homestead, this 160 year old 80 acre farm is located in the heart of the Kettle Moraine near Holy Hill.

  • Seasonal events:

    • Art & Farm Market weekends (June, September, October): local artisan booths, farm-fresh food, music, workshops holyhillartfarm.com+3TravelWisconsin+3LocalHarvest+3.

    • Music on the Farm series: barn concerts with tribute bands like Supertramp beneath 30-ft oak beams—plus wine, local fare, and bonfires Eventbrite+2Eventbrite+2Eventbrite+2.

    • Barn dances & themed dinners: like chili cook-offs, barn dances under the stars, art workshops, and dinner nights .

  • Why it’s great for couples:

    • Romantic farm atmosphere with creative and culinary experiences

    • Mid-wedding-event potential—relaxed elegance without being pretentious

    • Beautiful open space and bonfire settings make for special, date-worthy evenings

Terrace 167, located near Milwaukee, Oshkosh, Appleton and Madison, Wisconsin is a locally owned wedding venue. We have been in the business for 9 years. We love supporting other locally owned venues and are dedicated to using our platform to support them. In every blog we write, we will include 5 to 10 locally owned wedding venues that use their articles to support their colleagues and the wedding industry in ways that are not always recognized but are essential. If you are searching for a wedding venue, please consider a locally owned venue!

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For more wedding inspiration, planning tips, and engagement advice, be sure to follow Terrace 167 on Facebook, Instagram, Pinterest, and TikTok. Let’s make your dream day a reality!

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