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    • 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

    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

    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

    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

    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

    Burn Boot Camp Oconomowoc’s Annual North Pole Party

    Burn Boot Camp Oconomowoc 1061 Summit Avenue, Oconomowoc, WI, United States

    SANTA IS COMING TO OCONOMOWOC! Burn Boot Camp Oconomowoc’s Annual North Pole Party is BACK, and you won’t want to miss the magic at this 5th event! MEMBERS & NON-MEMBERS, EVERYONE IS WELCOME! Bring your family, invite your friends, and come make unforgettable Christmas memories with us! NOVEMBER 22 11 AM – 2 PM Burn...

    Free

    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

    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

    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

    • 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