Children
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
Soda with Santa
Sprecher, Milwaukee’s original craft brewery, in operation since 1985, announced that its Soda with Santa tradition is returning to their Glendale headquarters at 701 W. Glendale Avenue, Sunday November 16, 30; December 7, and 14 at 11:30 am, 12:30 pm 1:30 pm and 2:30 pm. According to Sharad Chadha, president and CEO of Sprecher “This fun event has become...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
German Christmas Market, Oconomowoc
The German Christmas Market is Celebrating its 14th 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. 2025 Dates: Thanksgiving Weekend...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
German Christmas Market, Oconomowoc
The German Christmas Market is Celebrating its 14th 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. 2025 Dates: Thanksgiving Weekend...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
German Christmas Market, Oconomowoc
The German Christmas Market is Celebrating its 14th 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. 2025 Dates: Thanksgiving Weekend...
Crescendo Christmas Market at Oakwood Church
Crescendo Christmas Market at Oakwood Church – Make intentional, local impacts with your holiday shopping! Enjoy the sounds of the season while purchasing gifts from local artisans who are donating 10% of their proceeds to local organizations. Various ensembles will play live music while shoppers browse and dine. At 5 p.m., the market will close...
Watertown Holiday Parade of Lights
On November 29, 2025 start your holiday season with the merchants in beautiful downtown Watertown . This is your opportunity to enjoy family friendly holiday activities and the Watertown Holiday Parade of Lights. The parade features more new units this year, bands, choirs, and floats. The parade begins at 5:30 pm in downtown Watertown. Pull...
German Christmas Market, Oconomowoc
The German Christmas Market is Celebrating its 14th 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. 2025 Dates: Thanksgiving Weekend...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
Soda with Santa
Sprecher, Milwaukee’s original craft brewery, in operation since 1985, announced that its Soda with Santa tradition is returning to their Glendale headquarters at 701 W. Glendale Avenue, Sunday November 16, 30; December 7, and 14 at 11:30 am, 12:30 pm 1:30 pm and 2:30 pm. According to Sharad Chadha, president and CEO of Sprecher “This fun event has become...
MainStage Academy of Dance Presents: The Nutcracker
MainStage Academy of Dance Presents: The Nutcracker MainStage Academy of Dance presents: The Nutcracker! (Featured event) Going to see Tchaikovsky’s beloved ballet at the Oconomowoc Arts Center has become a holiday tradition in the Lake Country Area. With Artistic Director Eddy Bray’s all-new choreography, Local dancers, amazing set design, and the magical musical score of...
Special Saturday
Join the Oconomowoc Public Library for their Special Saturday: Hands On Holidays Visit a variety of holiday crafting stations with all supplies provided for adults, teens, and kids to make gifts to share. The Oconomowoc Public Library provides materials, services, facilities, technology and up-to-date resources and programs to meet the educational, informational, cultural, and recreational...
Home for the Holidays at Old World Wisconsin
What is Home for the Holidays at Old World Wisconsin? Ready for a picturesque Victorian winter full of bustling shops, scenic stops and endless good cheer? Experience it all at Home for the Holidays, where you’ll stroll through a charming 1800s village filled with crackling bonfires, festive greenery and fun-filled craft making. Create your very...
“Letters To Santa” Mailbox at The Smiley Barn
Bring your kids or grandkids to The Smiley Barn to write a letter to Santa and put it directly into a certified “Letters to Santa” mailbox. All mail is guaranteed to make it to the big man himself! Find the “Letters To Santa” Mailbox at The Smiley Barn daily November 10 – December 24, 2025...
Watertown Outdoor Live Nativity
Kick off the Christmas season with this outdoor live portrayal of the true story of Jesus’ birth in Watertown. Get a glimpse into what it might have been like that very first Christmas – real animals and all! The Watertown outdoor live nativity will be the first weekend in December. Following the performance, meet the...
An Enchanted Christmas at Glacier Rock Farms
Find family fun and adventure at Glacier Rock Farms as they present “An Enchanted Christmas.” Get ready to step into our Wisconsin wonderland! Glacier Rock Farms is transforming into an Enchanting Christmas experience that will touch the hearts of all guests, regardless of age. If you come to Hartland Kids Day in the summer, then...