Romantic Date Night Ideas Winter Edition Lake Country Family Fun Date Night Guide

8 Romantic Date Ideas in Lake Country – Winter Edition

Winter is here, New Year’s is over, and everyone’s turned into a hibernating bear. Sound about right? I do love to hunker down at home by the cozy fireplace, but there are so many fun opportunities to go out and enjoy the Wisconsin winter with your significant other. There’s even plenty to enjoy way before Valentine’s Day arrives. So if you are a Lake Country couple looking for ideas for romantic dates and even more specifically, date ideas for this cold weather season.  …Lake Country Family Fun to the rescue! We’ve put together a categorized, winter-specific, date list for you and your loved one.  So book that babysitter, make those plans and enjoy this month of love.

*Bonus sitter option in Waukesha on February 15 from 5:00- 8:00 pm.


Please thank our Winter Date Guide Sponsor:

ID Date Night Guide

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. 


Painting & Art




Beer & Wine Experiences

  • Raised Grain Brewery (website)
  • Delafield Brewhaus (website)
  • Spring City Wine House in Waukesha (website)
  • Mr. Brew’s Taphouse in Menomonee Falls (website)
  • Vino Ectera in Oconomowoc (website)
  • Three Cellars in Menomonee Falls (website)
  • Bernie’s Tap Room in Waukesha (website)
  • Craft Beer Cellar Pewaukee (website)
  • The Hive Taproom East Troy (website)

ID Date Night Guide


Finer Dining

  • I.d.- Make your next date-night a shared-plate night!  (website)
  • Belfre Kitchen Delafield (website)
  • Butler Inn Pewaukee (website)
  • Palmer’s Steakhouse Hartland (website)
  • Golden Mast Okauchee (website)
  • Seven Seas Nagawicka Lake (website
  • Zin in Delafield (website)
  • Kurt’s Steakhouse Delafield (website)
  • Artisan 179 Pewaukee (website)
  • Mr. B’s Bartalotta’s Brookfield (website)
  • The Union House Genesee Depot (website)
  • Asiana Pewaukee (website)
  • Ninja Habachi Sushi in Menomonee Falls (website)
  • Lagniappe Brasserie New Berlin (website)
  • Red Circle Inn Nashotah (website)
  • Zesti Hartland (website)
  • Melting Pot Brookfield (website)
  • Coopers Hawk in Brookfield (website)
  • David Alan’s SmokeHouse Mukwonago (website)
  • Bass Bay Brewhouse in Muskego (website)
  • Lago Su Bella in Oconomowoc (website)
  • Twisted Fire in Oconomowoc (website)


Active Fun


Couples Massage/Spa Services

  • Woodhouse Day Spa in Mukwonago (website)
  • Spargo in Pewaukee (website)
  • Elegance Salon & Spa in New Berlin (website)
  • Absolute Necessities Day Spa in Menomonee Falls (website)


Stay-at-home Ideas

  • Board Game Night or Card Games – Do you know how to play Cribbage? Ask me!
  • Buy a Make Your Own 6-pack from Total Wine and have an at-home beer tasting date
  • Make a fancy Dinner after kids go to bed (Try this one)
  • Take a ‘ how well do you know each other’ quiz.

Coffee Shops in Lake Country Family Fun

Other Ideas:

Valentine Craft Open House Delafield Public Library Waukesha Public Library Pewaukee Public Library

Specific Events around Valentine’s Day 2020

  • Bourbon, Bordeaux, and the Blue on 1/16 in Pewaukee.
  • Cafe Benelux Ice Bars open 1/17 in the Third Ward in MKE and will continue until Mother Nature melts them away.
  • Ice Castles Lake Geneva hopes to open soon!
  • Lake Country Playhouse – Mars Lost AT LAKE COUNTRY PLAYHOUSE on January 31, February 1, 2, , 7, 8, 9, 13, 14, 15, and 16!
  • Cupid Studio opens in Milwaukee January 31 through February 23.
  • Attend Guinness, Chocolate, and Music – featuring the Whiskey Belles on 2/1 (limited tickets)
  • See a Valentine Show at the Waukesha Planetarium on 2/14 (tickets)
  • Take a romantic stroll under the Domes at their Hearts Under Glass event on 2/14
  • Couple’s Night Out at Brooklife Church
    • 2/14
    • It’s a unique entertainment experience full of laughter & games—all while celebrating & building into your relationship. 
  • Tacos and Tequila Bus Tour 2/15 6:30 PM – 9:30 PM
    • Milwaukee Food & City Tours
      2419 N 62nd Street, Wauwatosa, Wisconsin 53213
    • Included in the per person price, attendees will enjoy:
      • A bus tour with 3 stops for a taco, sope and fajitas, with each paired with a half-sized margarita or tequila-infused drink. And, be sure to save room for dessert!
      • Round trip transportation – help keep Milwaukee safe and leave the driving to us!
      • Narrated, guided tour fun
      • Tickets 
  • Murder Mystery Dinner – Til Death Do Us Part 2/15 6 PM – 10 PM
    • The Abbey Resort
      269 Fontana Blvd, Fontana, Wisconsin 53125
    • Til Death Do Us Part: All is fair in love and murder
      The birds are chirping, the sun is shining, but the wedding bells aren’t ringing for this not-so-happy couple when a member of the wedding party is murdered! Trade clues with the other party members and help solve the mystery of whodunnit. Get into the fun by wearing your own wedding dress or the most ridiculous wedding attire you can come up with.
    • Dinner menu
  • Valentine’s Prime Rib Buffet 2/15 5 PM – 10 PM
    • 240 West
      269 Fontana Boulevard, Fontana, Wisconsin 53125
    • Delight in the numerous options of this delicious prime rib dinner in 240° West each Saturday evening. Enjoy classic favorites as well as seasonal specialties brought to you by The Abbey Resort’s culinary team.
    • $32 Adults / $18 Children ages 6-12 / $8 Children ages 2-5
    • Sample Menu
    • Reservations/cost: $75 per person
    • Reservations Required, Call (800)709-1323
  • Weekend Brunch 2/15 8 AM – 2 PM
    • The Waterlin
      N88W14750 Main Street, Menomonee Falls, Wisconsin 53051
    • Brunch draws us together for great food, drink and company. They welcome visitors and locals alike to Menomonee Falls who seek an interactive experience coupled with creative midwestern fare. Waterlin provides an approachable brunch experience that both guests and locals have been craving. Gluten-free, vegetarian, and vegan options available. 
    • Tickets
  • Date Night: Raclette, Red Wine and Romance  2/15  5 PM – 7 PM

    • Village Cheese Shop
      1430 Underwood Ave, Wauwatosa, Wisconsin 53213
      (414) 488-2099

    • Enjoy the one you love! Join in for a romantic evening. Traditional Raclette smothered over a plate of oven baked potatoes, Italian herbed ham and cornichon. Enjoy with a flight of 3 red wines and finish with a chocolate covered strawberry.

      $45/person, plus tax

  • Beer and Wine Tasting at the Cotton Exchange in Waterford.
  • Mama D’s Coffee Shop Events (at the Wales location only)
  • Oconomowoc Junior Woman’s Club Annual Auction
    • 3/3
    • “The Reasons We Love Wisconsin” 
      • Food will include Wisconsin favorites, like brats, pretzels, cheese and other yummy treats
      • Live and silent auction items donated by local businesses and OJWC members
      • Every year the OJWC raises funds that go directly back to our community through service and charity, including Family of the Month program, Coats for Kids, Blessings in a Backpack, Helen Farnsworth Mears Art Contest, Food Pantry Easter Baskets with senior members at Wilkinson Woods and more.
      • Bring a donation for the Oconomowoc Food Pantry. If you bring a 4-pack of toilet paper, jar of peanut butter, 2 boxes of Mac & Cheese or 1 family size, you will receive 1 additional raffle ticket for each item(s).
      • Free to attend
  • Attend Oconomowoc Brewfest with your date on 3/7 Celebrate with over 30 different beer,wine, and food vendors, a fun atmosphere and a chance to help out the local community and the world! (event)

Winter Date Night Guide
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