Romantic Date Ideas in Lake Country – Winter Edition

Winter is here, 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 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.

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

  • Uptown Art Sussex (website)
  • Board & Brush Hartland – Wine and Painting Wood Sign Studio (website)
  • A Stroke of Genius Waukesha (website)
  • Soul Fire Art Studio Delafield (website)
  • Creative Art & Wine Studio New Berlin (website)
  • The Rustic Orchid creative workshop Mukwonago (website)
  • Creative Arts Oasis (website)




Beer & Wine

  • Raised Grain Brewery (website)
  • Delafield Brewhaus (website)
  • Spring City Wine House in Waukesha (website)
  • Rocky’s Hops & Leisure in Oconomowoc (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 Summer Date Guide Ad

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)


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 (Coming Soon)

  • Ice Castles Lake Geneva hopes to open soon!
  • Attend “MKE Ice Bars” open daily through 2/6 (event)  Enjoy drinks outside in three different hand-carved ice bars located at St. Paul Fish, Café Benelux, and The Wicked Hop and a portion of proceeds will be donated to charity. Ice carving by Guinness World Record holder Max Zuleta of Art Below Zero.
  • Lake Country Playhouse – The Explorers Club shows AT LAKE COUNTRY PLAYHOUSE ON February 1, 2, 3, 7, 8, 9, and 10!
  • PIX FLIX for $5 a ticket at the Waukesha Civic Theatre on 2/11
  • My Funny Valentine at 7:30 on 2/14 at the Waukesha Civic Theatre (tickets)
  • See a Valentine Show at the Waukesha Planetarium on 2/14 (tickets)
  • The Rep Theatre Plays tickets throughout February 
  • Attend Guinness & Chocolate: 200 Years of Guinness in America Celebration Concert by CelticMKE on 2/8 (limited tickets)
  • Skyzone – Lots of special events throughout the month.
  • Uptown Art Studio – Live Music Valentine’s Paint Party on 2/9
  • See a show at the Riverside Theater (tickets)
  • Take a romantic stroll under the Domes at their Hearts Under Glass event on 2/14
  • Milwaukee Bucks game on 2/6 , 2/9, 2/21, and 2/23 (tickets)
  • Milwaukee Admirals games on 2/1, 2/2, 2/6, 2/8, 2/9, and 2/11 (tickets)
  • Legends of Country and My Fair Lady at the Fireside Theatre throughout February
  • Matilda the Musical throughout February at Marcus Center for the Performing Arts (tickets)
  • Mama D’s Coffee Shop Events (at the Wales location only):
    • Thursday, 2/14 Stan Markus is playing with Jeff Leonard
    • Thursday, 2/21 Stan Markus and Steven Vaugn (live music) from 7-9pm. Especially for February, it will be such a treat to hear him play every night…it’s got romantic, intimate touches…perfect for a date night!
    • Thursday, 2/28 Paul Sundheim (live music)
  • Attend Oconomowoc Brewfest with your date on 3/2 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)

Find more February Fun here.

Want to be included in this Guide?

If you are a local business and feel that you would be a great addition to this guide, please email lakecountryfamilyfun (at) gmail (dot) com today or go to our Advertise With Us contact form.