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  • Ladies Night Out

    Downtown Delafield

    The seasonal Ladies Night Out Series is a three-night shopping extravaganza in Downtown Delafield that happens twice a year. Shops, restaurants, bars, and more offer deals and specials for all the shoppers. Hundreds of ladies grab their girlfriends and head out for a fun night on the town. Participants and businesses have a blast shopping...

    Free

    Illuminated Walk Through Country Christmas

    The Ingleside Hotel 2810 Golf Road, Pewaukee

    Illuminated Walk Through Country Christmas, benefiting Christmas Clearing Council of Waukesha County, starts in November for SEVEN nights in 2026! This is a favorite event of the Lake Country Family Fun team. Erin and her girls attended the first year in 2019 and nearly every year since. In fact, her children prefer the walking night...

    $10

    Home Plate for the Holidays

    American Family Field 1 Brewers Way, Milwaukee, WI, United States

    Capture the magic of the season with an exclusive photo experience at home plate. Gather your family and create an unforgettable holiday memory! Each photo session includes a custom scoreboard message and an optional Bernie Brewer appearance with a minimum of 3 high-resolution digital photos, giving you the perfect keepsake for holiday cards and memories...

    Peck and Bushel Winter Market

    Peck & Bushel Fruit Company 5454 County Road Q, Colgate, WI

    We are HUGE fans of Peck and Bushel. Our family goes there every fall to pick apples. The kids love the samples and the caramel apple bar. I love the picturesque barn, grounds, and orchard, and best of all the organic apples. (I’m that mom (some days).) Now it’s time for some holiday cheer! Peck...

    Free

    re:Craft and Relic Once upon a Holiday Market

    Milwaukee County Sports Complex 6000 W Ryan Rd, Franklin, WI, United States

    This annual Holiday Market is held at the Milwaukee County Sports Complex in Franklin, WI and features 180 booths filled with vintage treasures, handmade goods, artisan foods and boutique finds. Food trucks, live music and mobile boutique trailers and so much more make this two-day shopping event a can’t-miss part of your holiday season! Strollers...

    $1 – $10

    Kids Market at Country Christmas

    The Ingleside Hotel 2810 Golf Road, Pewaukee

    Kids Market at Country Christmas at the Ingleside Hotel in Pewaukee Waukesha. Bundle up and bring the festive spirit—this Kids Markets pop-up at Country Christmas is the perfect place for kids to share their creativity and holiday cheer with hundreds of patrons! Register now so young entrepreneurs can showcase their handmade crafts, sweet treats, or...

    $10

    Illuminated Walk Through Country Christmas

    The Ingleside Hotel 2810 Golf Road, Pewaukee

    Illuminated Walk Through Country Christmas, benefiting Christmas Clearing Council of Waukesha County, starts in November for SEVEN nights in 2026! This is a favorite event of the Lake Country Family Fun team. Erin and her girls attended the first year in 2019 and nearly every year since. In fact, her children prefer the walking night...

    $10

    Peck and Bushel Winter Market

    Peck & Bushel Fruit Company 5454 County Road Q, Colgate, WI

    We are HUGE fans of Peck and Bushel. Our family goes there every fall to pick apples. The kids love the samples and the caramel apple bar. I love the picturesque barn, grounds, and orchard, and best of all the organic apples. (I’m that mom (some days).) Now it’s time for some holiday cheer! Peck...

    Free

    re:Craft and Relic Once upon a Holiday Market

    Milwaukee County Sports Complex 6000 W Ryan Rd, Franklin, WI, United States

    This annual Holiday Market is held at the Milwaukee County Sports Complex in Franklin, WI and features 180 booths filled with vintage treasures, handmade goods, artisan foods and boutique finds. Food trucks, live music and mobile boutique trailers and so much more make this two-day shopping event a can’t-miss part of your holiday season! Strollers...

    $1 – $10

    Illuminated Walk Through Country Christmas

    The Ingleside Hotel 2810 Golf Road, Pewaukee

    Illuminated Walk Through Country Christmas, benefiting Christmas Clearing Council of Waukesha County, starts in November for SEVEN nights in 2026! This is a favorite event of the Lake Country Family Fun team. Erin and her girls attended the first year in 2019 and nearly every year since. In fact, her children prefer the walking night...

    $10

    Bird Club Meetings

    Retzer Nature Center S14-W28167 Madison St, Waukesha, WI, United States

    The Benjamin F. Goss Bird Club provides an opportunity for those interested in active study of birds and their habitats. The public is invited to attend the monthly Bird Club Meetings in-person, led by expert guest speakers and members.   About the Retzer Nature Center: Retzer Nature Center was John and Florence Retzer’s retirement home....

    Free

    Environmental Education Outdoor Classroom for Kids at Retzer Nature Center

    Retzer Nature Center S14-W28167 Madison St, Waukesha, WI, United States

    Environmental Education Outdoor Classroom for Kids at Retzer Nature Center. Learn and discover in the great outdoors! This program offers guided, hands-on exploration that brings seasonal topics to life for children ages 4-12. Families, caregivers, home school groups, scout troops and more…supplement your learner’s virtual education experience with an environmental education outdoor classroom program at...

    $6

    Peck and Bushel Winter Market

    Peck & Bushel Fruit Company 5454 County Road Q, Colgate, WI

    We are HUGE fans of Peck and Bushel. Our family goes there every fall to pick apples. The kids love the samples and the caramel apple bar. I love the picturesque barn, grounds, and orchard, and best of all the organic apples. (I’m that mom (some days).) Now it’s time for some holiday cheer! Peck...

    Free

    Holiday Folk Fair International

    State Fair Park 640 S. 84th St, West Allis, WI, United States

    Explore music, food, dance, and arts from around the world at Holiday Folk Fair International, Wisconsin’s premier multicultural festival. This one-of-a-kind cultural experience is taking place Friday, November 20 through Sunday, November 22, 2026 at the Wisconsin State Fairgrounds. The Holiday Folk Fair brings together dozens of cultures for a weekend of music, dance, food...

    Free – $16

    Craft Saturdays at the Brookfield Library

    Brookfield Library 1900 N Calhoun Rd, Brookfield, WI, United States

    Craft Saturdays at the Brookfield Library – This event is for ages 3-12: Make a seasonal craft! While supplies last. Come early, but they will try to have enough supplies to last all day. Third Saturday every month until December 19, 2026.   About the Brookfield Library: The Brookfield Public Library is established under the...

    Peck and Bushel Winter Market

    Peck & Bushel Fruit Company 5454 County Road Q, Colgate, WI

    We are HUGE fans of Peck and Bushel. Our family goes there every fall to pick apples. The kids love the samples and the caramel apple bar. I love the picturesque barn, grounds, and orchard, and best of all the organic apples. (I’m that mom (some days).) Now it’s time for some holiday cheer! Peck...

    Free

    Holiday Folk Fair International

    State Fair Park 640 S. 84th St, West Allis, WI, United States

    Explore music, food, dance, and arts from around the world at Holiday Folk Fair International, Wisconsin’s premier multicultural festival. This one-of-a-kind cultural experience is taking place Friday, November 20 through Sunday, November 22, 2026 at the Wisconsin State Fairgrounds. The Holiday Folk Fair brings together dozens of cultures for a weekend of music, dance, food...

    Free – $16

    Aspire Nutcracker Tea

    Aspire Dance Center W238 N1700 Rockwood Drive, Pewaukee, WI, United States

    Our partners at Aspire Dance Center are bringing a holiday classic to life in 2026: Aspire Nutcracker Tea! The Nutcracker Tea is coming soon!!! Save the date to be a part of this annual holiday tradition! This year they will be performing a 30-minute excerpt of The Nutcracker ballet, visiting the Land of the Snowy...

    $5

    The Corners of Brookfield Tree Lighting

    The Corners of Brookfield 20111 W. Bluemound Road, Brookfield, WI

    Join the Town of Brookfield at The Corners for a holiday tree lighting to kick off the season in 2026! Discover Brookfield, the Town of Brookfield & The Corners have teamed up this year to bring back a community favorite! The Holiday Town Tree Lighting Celebration presented by Aspire Dance Center & Landmark Credit Union,...

    Free

    Illuminated Walk Through Country Christmas

    The Ingleside Hotel 2810 Golf Road, Pewaukee

    Illuminated Walk Through Country Christmas, benefiting Christmas Clearing Council of Waukesha County, starts in November for SEVEN nights in 2026! This is a favorite event of the Lake Country Family Fun team. Erin and her girls attended the first year in 2019 and nearly every year since. In fact, her children prefer the walking night...

    $10

    Peck and Bushel Winter Market

    Peck & Bushel Fruit Company 5454 County Road Q, Colgate, WI

    We are HUGE fans of Peck and Bushel. Our family goes there every fall to pick apples. The kids love the samples and the caramel apple bar. I love the picturesque barn, grounds, and orchard, and best of all the organic apples. (I’m that mom (some days).) Now it’s time for some holiday cheer! Peck...

    Free

    Holiday Folk Fair International

    State Fair Park 640 S. 84th St, West Allis, WI, United States

    Explore music, food, dance, and arts from around the world at Holiday Folk Fair International, Wisconsin’s premier multicultural festival. This one-of-a-kind cultural experience is taking place Friday, November 20 through Sunday, November 22, 2026 at the Wisconsin State Fairgrounds. The Holiday Folk Fair brings together dozens of cultures for a weekend of music, dance, food...

    Free – $16

    Aspire Nutcracker Tea

    Aspire Dance Center W238 N1700 Rockwood Drive, Pewaukee, WI, United States

    Our partners at Aspire Dance Center are bringing a holiday classic to life in 2026: Aspire Nutcracker Tea! The Nutcracker Tea is coming soon!!! Save the date to be a part of this annual holiday tradition! This year they will be performing a 30-minute excerpt of The Nutcracker ballet, visiting the Land of the Snowy...

    $5

    Illuminated Walk Through Country Christmas

    The Ingleside Hotel 2810 Golf Road, Pewaukee

    Illuminated Walk Through Country Christmas, benefiting Christmas Clearing Council of Waukesha County, starts in November for SEVEN nights in 2026! This is a favorite event of the Lake Country Family Fun team. Erin and her girls attended the first year in 2019 and nearly every year since. In fact, her children prefer the walking night...

    $10

    Children’s Story Time at River Coffee

    River Coffee Oconomowoc 1260 Brown Street, Oconomowoc, United States

    Children’s Story Time at River Coffee STORY TIME IS COMING TO RIVER COFFEE! Looking for something fun to do with the kids on a Monday? Come cozy up with us for Story Time at River Coffee! Every 2nd and 4th Monday through November, the staff will be gathering for a story and some coloring fun,...

    German Christmas Market, Oconomowoc

    Village Green Park Oconomowoc 104 E. Wisconsin Avenue, Oconomowoc, WI, United States

    The German Christmas Market is Celebrating its 15th Anniversary! The German Christmas Market is an amazing event. It is not to be missed. It’s great to go with adults and with the family. Don’t forget to take your picture with Santa! *A Lake Country Family Fun Fan Favorite Event. Not sponsored. 2026 Dates: Thanksgiving Weekend...

    Free

    German Christmas Market, Oconomowoc

    Village Green Park Oconomowoc 104 E. Wisconsin Avenue, Oconomowoc, WI, United States

    The German Christmas Market is Celebrating its 15th Anniversary! The German Christmas Market is an amazing event. It is not to be missed. It’s great to go with adults and with the family. Don’t forget to take your picture with Santa! *A Lake Country Family Fun Fan Favorite Event. Not sponsored. 2026 Dates: Thanksgiving Weekend...

    Free

    Crescendo Christmas Market

    Oakwood Church 3041 Oakwood Rd, Hartland, WI, United States

    Crescendo Christmas Market ~Local Artisans~Purchase Christmas presents from local artisans at the Christmas Market from 12 – 5 p.m. ~Exceptional Music~Take in the sounds of the season from local musicians while you shop. Stay for the Gracenotes Orchestra Christmas concert at 5 p.m. ~Intentional Impact~At least 10% of all purchases will go back into the...

    Free

    German Christmas Market, Oconomowoc

    Village Green Park Oconomowoc 104 E. Wisconsin Avenue, Oconomowoc, WI, United States

    The German Christmas Market is Celebrating its 15th Anniversary! The German Christmas Market is an amazing event. It is not to be missed. It’s great to go with adults and with the family. Don’t forget to take your picture with Santa! *A Lake Country Family Fun Fan Favorite Event. Not sponsored. 2026 Dates: Thanksgiving Weekend...

    Free

    Wagon Rides through Country Christmas Lights

    The Ingleside Hotel 2810 Golf Road, Pewaukee

    Wagon Rides – Wagon Rides through Country Christmas provide a unique and fun way to see the holiday lights. When are the Wagon Rides through Country Christmas? November 29, 2026 – December 3, 2026 December 6 – 10, 2026 December 13 – 17, 2026 The Wagon Rides are at 5:15pm, 6:00pm, 6:45pm, 7:30pm, and 8:15pm and...

    $20