The Holiday Fun Guide is sponsored by the Ingleside Hotel presenting their Country Christmas Light Display.
Lake Country Family Fun has put together a one-stop guide that consolidates all your Holiday and Christmas events and fun into one place. First, read about our sponsor, the Ingleside Hotel’s County Christmas. Then use the guide to find great local Christmas and Holiday fun for you and your family. Please thank all of the local sponsors that make Holidays in Waukesha County a breeze to navigate:
- Holiday Fun Guide sponsored by Ingleside Hotel
- Christmas Parade Guide sponsored by the Delafield Brewhaus
- Christmas Tree Farm Guide sponsored by Aspire
- Christmas Tree Lighting Guide sponsored by the Hartland Lights
- Holiday Craft Fair Guide sponsored by Brown Street Emporium
- Holiday Light Displays Guide sponsored by River Coffee
- Can’t Miss Christmas Events – sponsored by Smiley Barn
- Thanksgiving Guide – sponsored by Smiley Barn
- Photos with Santa Guide – sponsored by Kara Reese Photography
- Christmas Break Guide – sponsored by Dayspring Church & Schools
- Holiday Drop and Shop Guide – sponsored by Craft & Relic’s two markets
- Live Nativities Guide – sponsored by St. Matthews Oconomowoc
HOIDAY FUN GIVEAWAY 2023
This year, we have put together an awesome package thanks to local sponsors to kick off our Holiday Season. One lucky winner will win:
- 1 carload pass to Country Christmas Light Display at the Ingleside Hotel + a Four Pack of Water Park Tickets
- 2 VIP Passes to MKE Improv each of which can be redeemed for two General Admission tickets, and are not time-sensitive
- 2 drink minimum required
- 1 free relaxation salt cave/sauna/family salt room pass to Salt Spot Oconomowoc
- $50 Promo Certificate to Delafield Brewhaus and a Brewhaus Beanie Cap
- $50 from Pine Hill Farm Wellness Collective & Market
- 4 tickets to the Take Flight Theatre’s Polar Express Journey at the Wilderness Hotel
- Does not include hotel stay. Other exclusions and limitations apply. Physical tickets will be mailed to the winner.
THANK YOU TO EVERYONE WHO ENTERED!
CONGRATULATIONS TO MICHELLE N. for WINNING!
Categories in this guide include:
Click a category below to jump to that category.
DAYS UNTIL CHRISTMAS...
(not that we are counting)
2023 HOLIDAY FUN GUIDE SPONSOR
A HUGE Holiday thank-you to our Holiday Fun Guide Sponsor, The Ingleside Hotel presenting the Country Christmas.
COUNTRY CHRISTMAS at the Ingleside Hotel is Wisconsin’s Largest outdoor drive-through light display and it begins soon for the 2023 season. Enter a separate giveaway to win one of 3 carload passes here from Nov 7 – 20.
Country Christmas is open November 24th, 2023 – November 29, 2023 & December 1, 2023 – January 1, 2024. Sunday through Thursday
Country Christmas is Wisconsin’s longest standing and most spectacular drive-through holiday lights event! Country Christmas features over a million holiday lights festively displayed along a mile-long trail that winds through the woods. You’ll experience enchanting animated figures and holiday scenes – all from the comfort of your car. And when you’ve finished your trip through the trail, leave your vehicle behind and visit Christmas Village and The Streets of Bethlehem. Christmas Village is home to our spectacular, working model train display as well as a concession area to purchase refreshments. The Streets of Bethlehem is where you will be amazed by the near life-size Fontanini nativity display, an exact replica of the one found at the Vatican.
Illuminated Walks –Join us November 17, 18, or 19th for an Illuminated Walk through Country Christmas. This three night only event will help benefit the Christmas Clearing Council of Waukesha County. Enjoy the mile long Country Christmas trail like you never have before. Hours are 5pm – 9pm, last admission tickets sold at 8pm. Admission is $8 per person with $2 donated directly to the Christmas Clearing Council.
Wagon Rides – Wagon Rides through Country Christmas provide a unique and fun way to see the holiday lights.
- November 26th – November 29th
- December 3th – 7th
- December 11th – 14th
Rides are at 5pm, 6pm, 7pm, and 8pm. Tickets are based on availability. $20 per person – Includes hot chocolate and a cookie. Purchase tickets in Christmas Village. Carload admission not required for wagon ride. Wagon rides will leave promptly at your scheduled departure time. Please dress appropriately for the weather.
HANDY HOLIDAY GUIDES
(CLICK ON THE IMAGES BELOW)
2023 Holiday Guides
CAN'T MISS LOCAL HOLIDAY EVENTS
- MILWAUKEE LIGHT FESTIVAL – November 16, 2023 – January 1, 2024
- GERMAN CHRISTMAS MARKET November 22, 24-26, 2023
- OUTDOOR LIVE NATIVITY at Shepherd of the Hills – December 9, 2023
- DOUSMAN WINTERFEST 2023 – December 3, 2023 (Dousman Santa is Coming to Town)
- COUNTRY CHRISTMAS DRIVE THROUGH LIGHT DISPLAY – Nov 24, 2023 – Nov 29, 2023, December 1st – Jan 1st, 2024
- Winter Wonders Drive Through Light Display – Nov 24 – Dec 31, 2023
- Janesville Jolly Jingle – December 1st to 3rd, 2023
- Midnight Magic in Mukwonago – December 2nd, 2023
- St. Matthews LIVE NATIVITY – December 16, 2023
- Dayspring’s annual Luminary Nativity Walk through event – Dec 9, 10, 16, and 17 in 2023
- Canadian Pacific Holiday Train December 4th, 2023!!!
- BREAKFAST WITH THE REINDEER – December 2nd, 2023
- BREAKFAST WITH THE KING at Divine Redeemer – December 2, 2023
- All of the local CHRISTMAS PARADES
- CHRISTMAS IN WALES – December 9, 2023
- Waukesha SILVER BELLS FESTIVITIES – The Tree lighting is December 1, 2023 and the Parade is December 3rd
- Local TREE LIGHTING Events
- EAST TROY SANTA TRAIN RIDE 2023 – Tickets on sale! Night trains sold out.
- Polar Express Take Flight Ride at the Wilderness – Take Flight Ride in 2023
MUST SEE PERFORMANCES
MAINSTAGE ACADEMY OF DANCE PRESENTS THE NUTCRACKER BALLET
MainStage Academy of Dance Presents: The Nutcracker
Don’t Miss This Beloved Holiday Favorite! December 15-17, 2023
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 Peter Tchaikovsky, the production delights audiences of all ages.
Tickets/Info:https://wedancemainstage.com/
The 11th ANNUAL Production of the delightful musical rendition of the Charles Dickens classic, A CHRISTMAS CAROL will be at the Lake Country Playhouse this Holiday season.
SHOW DATES
Saturday, Nov 25, 2:00pm and 6:00pm
Sunday, Nov 26, 2:00pm and 6:00pm
Thursday, November 30, 7:30pm
Friday, December 1, 7:30pm
Saturday, December 2, 2:00pm and 6:00pm
Sunday, December 3, 2:00pm and 6:00pm
Thursday, December 7, 7:30pm
Friday, December 8, 7:30pm
Saturday, December 9, 2:00pm and 6:00pm
Sunday, December 10, 2:00pm and 6:00pm
From the Director Robert Hurd:
– When Charles Dickens created this story I don’t know if he realised that he also created the perfect script! We honor his story through this adaptation by playwright MICHAEL KOSCINSKI and Music by ERNEST BRUSUBARDIS. Come and continue your Holiday tradition or start your own tradition this year!
Appropriate audience: All ages
Purchase your tickets HERE.
MAKE THESE HOLIDAY TRIPS
Looking for some holiday fun to get you and your family in the holiday spirit? Enjoy this list and get in touch with your jolly side 🙂
Note: Information posted below taken from websites with permission.
COUNTRY SPRINGS COUNTRY CHRISTMAS DRIVE THROUGH LIGHTS
PEWAUKEE, WI
COUNTRY CHRISTMAS at the Ingleside Hotel is Wisconsin’s Largest outdoor drive through light display and it begins soon for the 2023 season.
Country Christmas is open November 24th, 2023 – November 29, 2023 & December 1, 2023 – January 1, 2024. Sunday through Thursday hours are from 5-9 pm, and Fridays and Saturdays it runs from 5- 10 pm.
See details on the 2023 dates for Illuminated Walks and Wagon Rides.
OLD WORLD CHRISTMAS MARKET
ELKHART, WI
December 1-10, 2023!
The 2023 Old World Christmas Market is open daily from 10 AM – 5 PM, December 1 – 10, 2023. Admission is $7 per adult, children 14 and under are complimentary with an adult ticketholder. Discounted ticket prices for groups of 20 or more are available. Reminiscent of the centuries-old Christkindlesmarkt of Nüremberg, Germany, the 25th annual Old World Christmas Market at The Osthoff Resort offers the warmth and merriment of this Old World tradition.
For more information, please call (877) 517-4596.
AN OLD WORLD CHRISTMAS
EAGLE, WI
Select Sat & Sun | 10 AM – 3 PM
December 2-3, 9-10 and 16-17
Stroll through the charming 19th century Crossroads Village, where historic shops and cozy homes are decked in festive greenery and bustling with holiday cheer.
GUIDED TROLLEY TOUR OF LIGHTS
LAKE GENEVA, WI
Christmas in the Country 2023 and the Annual Illumination Ceremony
We invite all of our resort guests and the community to help us kick off our annual six-week Christmas in the Country Celebration on Sunday, November 19, 2023. We’ll flip the switch on more than two million lights throughout the resort and follow it up with our dazzling fireworks display. Roam the resort taking in all of the sights and sounds of the holidays and stroll through our Gingerbread House Walk. Plus activities for the kids, a visit from Santa, holiday cookies and hot apple cider.
Hop aboard the Grand Geneva trolley for a tour around the resort to see all of our decorations.
- Starting on Monday, November 20, 2023 (last Tour of Lights is Saturday, December 30)
- Tours available hourly at 5, 6, 7 and 8pm
- Admission is complimentary for resort guests and $20 per adult and $15 for children 3-12 years old for non-resort guests (children 2 and under are complimentary)
- Advance reservations are required for resort guests and non-resort guests
- Meet in the hall across from White River Gifts
- The trolley is heated and enclosed
CANDY CANE LANE
WEST ALLIS, WI
CANDY CANE LANE is in West Allis and is fundraising for the MACC Fund (Midwest Athletes Against Childhood Cancer).
WISCONSIN CHRISTMAS CARNIVAL OF LIGHTS
CALEDONIA
THE CHRISTMAS CARNIVAL OF LIGHTS
Open Nov. 18, 2023 – Jan. 1, 2024*
Relax in the comfort of your own vehicle as you wind your way through our campground’s winter wonderland, book your seat on Santa’s GIANT Sleigh or take a ride in our Golf Cart Holiday Train for a unique experience. Enjoy Christmas in the country with lights on all sides that are high above in the trees and one-of-a-kind hand-crafted displays.
*Excludes 11/23, 11/24 (open for Light Show 5K only), and Christmas Day
SHALOM HOLIDAY LIGHT DRIVE THROUGH
WEST BEND
After the Holiday drive-thru enjoy entrance into the petting zoo and a crackling camp fire. Animal feed for the petting zoo is available for purchase in the gift shop.
ENCHANTMENT IN THE PARK
WEST BEND
JOIN US FOR AN INTERACTIVE HOLIDAY LIGHTSHOW TO BENEFIT HUNGRY FAMILIES AND LOCAL
Details HERE.
BURLINGTON
City is delighted to host the Wisconsin State Ice Carving Championship as part of the 2023 Ice Festival on
Saturday, December 9 and Sunday December 10 , 2023
This event is free to the public and it is only made possible with the support of our community sponsors. Come see them at your convenience for the next few days (weather pending)!
Wehmhoff Square Park
355 N. Pine Street, Burlington, WI
LCFF HOLIDAY ARTICLES
15+ Ice Skating Rinks In and Around Waukesha County
12 Snowshoe Trails to Stride this Winter
Lake Country and Waukesha County Winter Fun Guide
30 Things to do Over Christmas Break
Kick Your Christmas Movie Night Up A Notch
How to Make your own Hot Chocolate Bombs
30 Best Christmas Movies Guide!
Holiday Light Displays that Amaze
Lake Country Family Fun’s Shop Small Guide
South East Wisconsin Christmas Tree Farms Guide
Where to Find Santa in Waukesha County in 2023
Country Christmas Drive Through Light Display
Holiday Fun Guide + Giveaway
Milwaukee Holiday Lights Festival
Santa Train Ride, East Troy Electric Railroad
Fall and Holiday Craft Fair Guide
Food Pantry Guide of Waukesha County
Breakfast with the Reindeer in Delafield
Slice of Ice-Red Arrow Park, Milwaukee
LAKE COUNTRY FAMILY FUN Year in Review: 2021
Our Family Experience at the Ingleside Hotel in Pewaukee
Ho Ho Humbug? Holiday Confessions About the Not-So-Easy Stuff
5 Ways to Stay Sane During Christmas Week
Ten Ways To Do Christmas [Right] This Year
Hot Cocoa in a Jar!
LIGHT DISPLAYS THAT AMAZE
Cookie Walks
- Oconomowoc Library Cookie Walk December 9, 2023 from 10:00 am to 2:00 pm
- Delafield Library Cookie Sale
December 3, 2022 from 9:30 am to 12:30 pm - Waukesha South Band Boosters Cookie Walk
- December 2 from 9 a.m. to noon (or until sold out).
- Homemade cookies $10 per pound, cash only.
- Shoppers are given a container to select their own cookies.
- Additional specialty baked goods will be individually priced.
- Visit Santa 9-11.
- Live music 9:30-10.
- Waukesha South High School, 401 E. Roberta Ave., Waukesha. Located in the cafeteria. Enter through Field House doors off Tenny Ave.
- Cookie/treat donations and volunteers also needed — sign up here: https://goo.by/aNJAPw
We also recommend popping over to our SHOP SMALL GUIDE and hitting up these local YUMMY EATS retailers:
Sweet P’s Pantry
E and S Sweets
All the Crumbs Cookies
The Naked Lemon Bakery
LAKE COUNTRY FAMILY FUN HAS ALL YOUR HOLIDAY NEEDS. CHECK OUT OUR HOLIDAY SHOP SMALL GUIDE, PHOTOS WITH SANTA GUIDE, CHRISTMAS TREE LIGHTING GUIDE, CHRISTMAS TREE FARM GUIDE, HOLIDAY CRAFT FAIR GUIDE, AND CHRISTMAS AND HOLIDAY PARADE GUIDE. HAPPY HOLIDAYS FROM LAKE COUNTRY FAMILY FUN!
HAPPY HOLIDAYS FROM LAKE COUNTRY FAMILY FUN!
ADD SOME HOLIDAY FUN
Enter to win the HOliday FUn Giveaway here:
One winner will receive:
- 1 carload pass to Country Christmas Light Display at the Ingleside Hotel.
- 2 VIP Passes to MKE Improv each of which can be redeemed for two General Admission tickets, and are not time-sensitive with 2-item minimum requirement
- 5 free session passes for our relaxation salt cave, infrared sauna or family salt room to The Salt Spot Oconomowoc
- A spa basket from Pine Hill Farm which will include a gift certificate
- 4 tickets to the Take Flight Theatre’s Polar Express Journey at the Wilderness Hotel
- $50 Promo Certificate to Delafield Brewhaus and a Brewhaus Beanie Cap
- 1, $25 Gift card to Fleet Farm
The contest runs Nov 1 – 30 11:59PM CST. Winner announced on December 1st. One entry per person. Duplicates will be deleted. To be entered to win, comment on the Facebook post from 11/1 at 7am and enter the form. Some product exclusions apply.
THANK YOU TO EVERYONE WHO ENTERED!
CONGRATULATIONS TO MICHELLE N. for WINNING!
GIVEAWAY DISCLOSURE:
Other: Entrants must be 18 years or older at the time of entering the giveaway. Entrants must be located in the U.S. The winner will be selected at random and notified via the email that was submitted. Winner must respond within 48 hours to claim their prize, or another winner will be chosen. Only one entry person. Duplicates will be deleted.
Disclosure: Many thanks to the many local sponsors for providing the giveaways (see individual giveaway for sponsorship details). See DISCLOSURE AND PRIVACY POLICY here. The winner may be congratulated on Facebook (with the official prize notification going through email). For giveaways that are announced or promoted on Facebook, please note that these promotions are in no way sponsored, endorsed or administered by, or associated with, Facebook.
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Merry Christmas
Merry Christmas!
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Awesome information!!
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Merry Christmas
This is a fantastic guide of things to do.
Thank you!! It truly is!
Thank you! We love the Delafield Christmas Tree 🎄 lighting and the German Christmas 🎅 Market in Oconomowoc!
Yay for all things CHRISTMAS!
Sounds AMAZING!!
What a great list of things to do in our awesome community!
It’s the most magical time of the year! ✨⭐️
Thank You for ALL this “LAKE COUNTRY FAMILY FUN” POST!
All the community Christmas events with family and our own light shows – Lights on Pleasant Heights.
LightsonPleasantHeights.com
Yeah I can’t wait for the best time of year, ice fishing soon