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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...

    $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...

    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....

    $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...

    $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...

    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....

    $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...

    $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...

    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...

    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...

    $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...

    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...

    $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...

    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,...

    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...

    $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...

    $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...

    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...

    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...

    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 –...

    $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 –...

    $20