Celebrate the holidays in Lake Country and Waukesha County!
Our Holiday Fun Guide brings together the best Christmas and holiday events across Oconomowoc, Delafield, Hartland, Pewaukee, Brookfield, and Waukesha, all in one magical list. Whether you’re looking for Christmas light displays, photos with Santa, local parades, craft fairs, or festive family activities, we’ve got you covered.
This year’s guide is proudly sponsored by The Ingleside Hotel, home of the beloved Country Christmas Light Display, a must-see tradition for families across Southeast Wisconsin (especially ours!).
Keep scrolling to find every local holiday happening, from tree lightings and live nativities to holiday shopping and Christmas break activities. Bookmark this page and check back often — Lake Country Family Fun keeps it updated all season long so you can make the most of your holiday fun in Waukesha County!
- Holiday Fun Guide sponsored by Ingleside Hotel
- Thanksgiving Guide sponsored by Bank Five Nine
- Holiday Craft Fair Guide sponsored by Brown Street Emporium
- Photos with Santa Guide – sponsored by Kara Reese Photography
- Best Holiday Light Displays Guide sponsored by Bank Five Nine
- Christmas Tree Lighting Guide sponsored by Roots Coffeebar and Cafe
- Christmas Parade Guide sponsored by the Delafield Brewhaus
- Christmas Tree Farm Guide sponsored by Aspire Dance Center
- Christmas Break Guide – sponsored by Dayspring Church & Schools
- Holiday Drop and Shop Guide – sponsored by Lake Country Currents
- Live Nativities Guide – sponsored by St. Matthews Oconomowoc
HOLIDAY & CHRISTMAS EVENTS GUIDE GIVEAWAY 2025
This year, we have put together an awesome package thanks to local sponsors to kick off our Holiday Season. Scroll to the bottom of this page to enter. One lucky winner will win:
- 1 carload pass to Country Christmas Light Display at the Ingleside Hotel + a Four Pack of Water Park Tickets to Springs Water Park
- 2 VIP Passes to MKE Improv at the Corners of Brookfield each of which can be redeemed for two General Admission tickets, and are not time-sensitive
- 2 drink minimum required
- A $50 Candle Set from Oak and Elizabeth
- 24K Gold Pvd Titanium Earrings featuring 3 Baguette cut CZs. Comfortable flat black labret posts are included from Piercings by Danielle – Elegant Edge in Brookfield
- 4 tickets to the Take Flight Theatre’s “Rudolph!” at the Wilderness Hotel in Wisconsin Dells.
- Does not include hotel stay. Other exclusions and limitations apply. Physical tickets will be mailed to the winner.
1 – Fill out the form below.
2 – Also comment on the Facebook post from 11/6/2025 AND/OR the Instagram post from 11/6/2025 OR if you do not have Facebook or Instagram, comment below on the website in the comment box with which prize you are most excited to win!
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2025 Giveaway will run November 6 – December 3, 2025 at 11:59 pm with the winner chosen on December 4, 2025 via the email used when filling out the form above. Please whitelist Lakecountryfamilyfun@gmail.com so you can receive your winning email!
CONGRATULATIONS TO STACEY H. of Oconomowoc for WINNING in 2024!
Christmas & Holiday Fun Guide
Table of contents
Click a category below to jump to that category.
DAYS UNTIL CHRISTMAS...
(not that we are counting…)
2025 CHRISTMAS & HOLIDAY FUN GUIDE SPONSOR
A HUGE Holiday thank-you to our Christmas & Holiday Fun Guide Sponsor,
The Ingleside Hotel presenting Country Christmas.
COUNTRY CHRISTMAS at the Ingleside Hotel is Wisconsin’s Largest outdoor drive-through light display and it begins soon for the 2025 season. Enter a separate giveaway to win one of three carload passes in November.
Country Christmas is open November 28, 2025 through December 2, 2025 & December 4, 2025 through January 3, 2026. Sunday through Thursday hours are from 5-9 pm, and Fridays and Saturdays hours are from 5-10 pm.
*Note that there are special nights and special promotions throughout the holiday season!
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!
Illuminated Walks:
Dates: November 14-16, 21-23 & 26, 2025
This seven-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.
Country Christmas Bikes and Lights:
Dates: November 24-25, 2025
Guests will be allowed to bike through the Country Christmas trail. Admission includes unlimited
number of trips through the trail on the event date selected. The trail will be closed to any drive through traffic on these special nights.
Wagon Rides:
Dates: November 30-December 2, December 4, December 7-11, and December 14-18, 2025
Ride a wagon to see the lights! On select nights, take in the lights of Country Christmas Trail from our Wagon Ride!
Brunch with Santa:
Date: December 21, 2025 | 9AM-1PM | Lake Country Ballroom
Make a reservation and enjoy a delicious buffet filled with sweet and savory favorites like pancakes, an omelet station, and of course desserts! There will be family-friendly activities to enjoy after your meal. Activities include a photo opportunity with Santa, arts and crafts, cookie decorating and more!
HANDY HOLIDAY GUIDES
(CLICK ON THE IMAGES BELOW)
2025 Holiday Guides
Ingleside Hotel
Bank Five Nine
sponsored by the Corners of Brookfield
sponsored by the Delafield Brewhaus
sponsored by Aspire Dance Center
at home!
shop more efficiently while the kids play!
featuring our 10 favorite local shops
CAN'T MISS LOCAL HOLIDAY EVENTS
- MILWAUKEE LIGHT FESTIVAL – November 20, 2025 thru January 1, 2026
- LAKE COUNTRY DANCE PRESENTS THE NUTCRACKER – November 22 and 23, 2025
- ASPIRE DANCE CENTER NUTCRACKER TEA – November 23 and 24, 2024 TBD in 2025
- GERMAN CHRISTMAS MARKET– November 26, 28-November 30, 2025
- DOUSMAN WINTERFEST 2025 – December 7, 2025 (Dousman Santa is Coming to Town)
- COUNTRY CHRISTMAS DRIVE THROUGH LIGHT DISPLAY – November 28, 2025 through December 2, 2025 & December 4, 2025 through January 3, 2026
- JANESVILLE JOLLY JINGLE – December 5th to 7th, 2025
- BREAKFAST WITH THE REINDEER DELAFIELD – December 6th, 2025
- MIDNIGHT MAGIC in MUKWONAGO – December 6th, 2025
- Dayspring’s annual LUMINARY NATIVITY WALK THROUGH EVENT – Dec 13, 14, 20, and 21, 2025
- CANADIAN PACIFIC HOLIDAY TRAIN December 10th, 2025
- DOWNTOWN WAUKESHA FESTIVITIES – The Tree lighting is December 5, 2024 and the Parade is December 7th
- Local TREE LIGHTING Events – Starting mid-November through the first weekend in December
- All of the local CHRISTMAS PARADES – Starting mid-November through the first weekend in December
- CHRISTMAS IN WALES – December 14, 2024 TBD on 2025
- St. Matthews LIVE NATIVITY – December 20, 2025
- EAST TROY SANTA TRAIN RIDE 2025 – Tickets on sale! Night trains sold out.
- AQUAVIA LUMINA and TAKE FLIGHT THEATRE’S “RUDOLPH!” AT THE WILDERNESS – New experiences in 2024; open in 2025!
MUST SEE PERFORMANCES
The 14th 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.
A Christmas Carol will run from November 28-December 14th, 2025. Performances will be held on Thursday and Friday nights at 7:30 pm, Saturday and Sunday afternoons at 2:00 pm, and Saturday and Sunday nights at 6:00 pm. Tickets are $27.50. Group pricing is also available. Tickets can be purchased online at www.lakecountryplayhousewi.org.
A Christmas Carol: the Musical – 17 PERFORMANCES:
Friday, November 28, 7:30pm – PREVIEW
Saturday, November 29, 2:00pm
Saturday, November 29, 6:00pm
Sunday, November 30, 2:00pm
Sunday, November 30, 6:00pm
Thursday, December 4, 7:30pm
Friday, December 5, 7:30pm
Saturday, December 6, 2:00pm
Saturday, December 6, 6:00pm
Sunday, December 7, 2:00pm
Sunday, December 7, 6:00pm
Thursday, December 11, 7:30pm
Friday, December 12, 7:30pm
Saturday, December 13, 2:00pm
Saturday, December 13, 6:00pm
Sunday, December 14, 2:00pm
*Possible added 6pm performance on Sunday December 14th. Tickets sell out quickly. Please join their waitlist if the performance you’re interested in is no longer available, or you would like to be contacted about the added performance.
MAINSTAGE ACADEMY OF DANCE PRESENTS THE NUTCRACKER BALLET
Don’t Miss This Beloved Holiday Favorite! December 5-7, 2025
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/
‘Twas the Night Before…by Cirque du Soleil at the Miller High Life Theatre.
Our team member Sam saw this performance in 2024 and loved it! She went on a date night with her husband, but relayed that her small children would have loved it, too!
- Nov. 26, 2025 / Wednesday 7:30 PM DOORS 6:30 PM
- Nov. 28, 2025 / Friday 1:00 PM DOORS 12:00 PM
- Nov. 28, 2025 / Friday 4:00 PM DOORS 3:00 PM
- Nov. 28, 2025 / Friday 7:30 PM DOORS 6:30 PM
- Nov. 29, 2025 / Saturday 1:00 PM DOORS 12:00 PM
- Nov. 29, 2025 / Saturday 4:00 PM DOORS 3:00 PM
Nov. 29, 2025 / Saturday 7:30 PM DOORS 6:30 PM
Nov. 30, 2025 / Sunday 12:00 PM DOORS 11:00 AM
Get tickets to ‘Twas the Night Before… by visiting their ticket website.
We’re excited to partner with Cirque DU Soleil to offer our Lake Country Family Fun followers 20% off select seats and price levels! (Other restrictions may apply.)
How to redeem the offer:
1. Select your preferred show date and time.
2. Under Available Offers, click “Buy Offer” in the Special Offers section.
3. On the next page, click “Select Tickets” and enter promo code CHEER to unlock the discounted
tickets.
4. This offer is valid until Wednesday, November 26 at 5:30 PM local time.
Dr. Seuss’ How The Grinch Stole Christmas! The Musical
Shows run from November 25 – November 30, 2025 at the Marcus Performing Arts Center.
Dr. Seuss’ How The Grinch Stole Christmas! The Musical features the hit songs “You’re A Mean One Mr. Grinch” and “Welcome Christmas” (written by Albert Hague and Dr. Seuss) from the original animated series. Max the Dog narrates as the mean and scheming Grinch, whose heart is “two sizes too small,” decides to steal Christmas away from the Holiday loving Whos. Magnificent sets (John Lee Beatty) and costumes (Robert Morgan) inspired by Dr. Seuss’ original illustrations help transport audiences to the whimsical world of Whoville, while the Music and Book of Mel Marvin and Timothy Mason breathe new life into this timeless story of the true meaning of Christmas.
The Pigeon Gets A Big Time Holiday Extravaganza!
Show runs November 21 to December 28, 2025 at the Marcus Performing Arts Center.
When Mo Willems’ characters get together for the holidays, it’s bound to be the biggest extravaganza ever! The Unlimited Squirrels deck the halls and Elephant and Piggie come ready to celebrate! But will The Pigeon join in the festivities, or will he run all the way to the North Pole in the search of the greatest gift ever? Catchy tunes, silly stories, goofy gifts, audience antics: it’s all in this brand-new musical party that sleighs!
Trans-Siberian Orchestra Tickets at Fiserv Forum
December 27, 2025 at the Fiserv Forum in Milwaukee
The holidays rock a whole lot harder than they ever have thanks to Trans-Siberian Orchestra. By infusing seasonal classics with rock flamboyance, a symphonic sense of scope, and an eye-popping visual presentation complete with lasers and pyrotechnics, what began as a side project for a veteran group of American hard rockers has grown into one of today’s top-selling acts, with over 10 million concert tickets sold since 1999.
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 2025 season.
See details on the 2025 dates for Illuminated Walks and Wagon Rides and NEW THIS YEAR: Country Christmas Bikes and Lights.
OLD WORLD CHRISTMAS MARKET
ELKHART, WI
December 5-14, 2025!
The 2025 Old World Christmas Market is open daily from 10 AM – 5 PM. Admission is $8 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 26th annual Old World Christmas Market at The Osthoff Resort offers the warmth and merriment of this Old World tradition.
For ten consecutive days, guests stroll the aisles of a grand heated tent bedecked with fragrant boughs of fresh evergreens and the tantalizing scents of roasted almonds as they browse for unique and specialty items among international and regional artisans. Czech blown-glass ornaments, Russian nesting dolls, German hand-carved smokers and nutcrackers, fine apparel, handmade amber and silver jewelry, Turkish pashmina scarves and shawls, stained glass art, Russian hand-painted Santas, fresh green wreaths, kissing balls and centerpieces, alpaca products, Estonia woolens, fine chocolates, Plauen lace, fine woodwork, fur products and much more!
The Old World Food Court offers shoppers space to relax and enjoy delectable German fare, such as hot glühwein, sauerbraten, dumplings, schnitzel, potato pancakes, red cabbage, pulled pork and apple strudel.
For more information, please call (877) 517-4596.
AN OLD WORLD CHRISTMAS
EAGLE, WI
Select Sat & Sun | 10 AM – 5 PM
December 6-7 & 13-14, 2025
We love Old World Wisconsin! And we love this event. Bundle up as most of it is walking outside through the crossroads Village.
Stroll through the charming 19th century Crossroads Village, where historic shops and cozy homes are decked in festive greenery and bustling with holiday cheer.
Give yourself the gift of memories you and your family will remember forever—and experience a treasured outing you’ll never forget—when you leave the modern-day hustle and bustle behind at Home for the Holidays.
GUIDED TROLLEY TOUR OF LIGHTS
LAKE GENEVA, WI
Hop aboard the Grand Geneva trolley for a memorable tour around the resort to see all of the decorations and outdoor light displays.
Enjoy the view with 3D glasses, transforming the vibrant lights into a mesmerizing spectacle, and sing-a-long to the 12 days of Christmas. Prepare to be entertained by Santa’s elves, who bring the holiday spirit to life. It’s not just a tour; it’s a joyous celebration of the holidays, leaving you with cherished memories and a heart full of festive delight.
- Starting on Monday, November 24, 2025 (no tours on Christmas Day, last Tour of Lights is Tuesday, December 30)
- Tours available hourly at 5, 6, 7 and 8pm and run about 30 minutes long
- Admission is complimentary for resort guests and $30 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 at the Concierge desk
- The trolley is heated and enclosed
Advance reservations are required and can be made starting October 24, most tours do sell out.
Resort Guests – Call (262) 248-8811 ext 3782 for reservations
Non-Resort Guests – reserve your tickets online soon
If you miss the trolley tour, don’t worry! You are welcome to ride in your own vehicle down Grand Geneva Way, starting at Hwy 50. The trolley tour is not necessary to see all our decorations, but a fun way to experience them.
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).
It runs November 28 through December 25th, and the hours are:
6:00 – 9:00 pm weekdays
6:00 – 10:00 pm Friday
5:00 – 10:00 pm Saturday
5:00 – 9:00 pm Sunday Please note that the hours may change due to weather, traffic, and other conditions. Donations highly recommended. The goal is to raise $ for the MACC Fund!
WISCONSIN CHRISTMAS CARNIVAL OF LIGHTS
CALEDONIA
THE CHRISTMAS CARNIVAL OF LIGHTS
November 22nd to December 31st*
*Closed for Thanksgiving (11/27) & Christmas (12/25)
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.
SHALOM HOLIDAY LIGHT DRIVE THROUGH
WEST BEND
ENCHANTMENT IN THE PARK
WEST BEND
JOIN IN FOR AN INTERACTIVE HOLIDAY LIGHTSHOW TO BENEFIT HUNGRY FAMILIES AND LOCAL
LCFF HOLIDAY ARTICLES
Thanksgiving in Lake Country
Holiday & Christmas Events Lake Country 2025 | Waukesha County WI
Christmas Tree Lighting Guide
Holiday & Christmas Parades 2025 | Lake Country & Waukesha
Fall and Holiday Craft Fair Guide
Milwaukee Holiday Lights Festival
Breakfast with the Reindeer Delafield 2025
Canadian Pacific Holiday Train to Return in 2025
Santa Train Ride, East Troy Electric Railroad
Country Christmas Drive Through Light Display
Take the Family to a Brewers Game and Enjoy Am Fam Field
How to Make your own Hot Chocolate Bombs
12 Snowshoe Trails to Stride this Winter
15+ Ice Skating Rinks In and Around Waukesha County
30 Best Christmas Movies Guide!
Waukesha Janboree
30 Things to do Over Christmas Break
Live Nativities around Waukesha County
Drop the Kids and Shop!
South East Wisconsin Christmas Tree Farms Guide
Lake Country Family Fun’s 2024 Holiday Wishlist
Lake Country Family Fun’s Shop Small Guide
15+ Holiday Lights Displays in Lake Country + Waukesha County
Where to Find Santa in Waukesha County in 2025
Food Pantry Guide of Waukesha County
Kick Your Christmas Movie Night Up A Notch
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](https://media.lakecountryfamilyfun.com/wp-content/uploads/2016/12/30153539/Untitled-design-1-450x253.webp)
Ten Ways To Do Christmas [Right] This Year
Hot Cocoa in a Jar!
15+ LIGHT DISPLAYS THAT AMAZE
Cookie Walks and Holiday Bake Sales
- Saturday and Sunday, November 22 and 23, 2025
Pauline Haass Holiday Book and Bake Sale
N64W23820 Main Street
Sussex, WI 53089
Join the Friends for $10/person to gain access to the Preview Sale from 4-6 PM on Friday, November 21. - Friday, December 5th and Saturday, December 6, 2025
10:00 am until 5:00 pm
Menomonee Falls Downtown District
121 Wisconsin Ave, Waukesha, WI 53186 - Saturday, December 13th, 2025
9:00 am until 1:00 pm (or while supplies last)
Oconomowoc Public Library
200 W. South Street, Oconomowoc, WI
If you’d like to donate cookies, they should be dropped off at the library starting Wednesday, December 10 through Saturday morning. - Saturday, December 7, 2024
9:00 am until 12:00 pm
First United Methodist Church
121 Wisconsin Ave, Waukesha, WI 53186
Cookie Walk located in the lower-level church dining room
For more information, call: 262-542-4256. - Saturday, December 7, 2024
9:00 am until the cookies are gone
Waukesha South High School
401 E Roberta Ave, Waukesha, WI
Waukesha South Band Boosters Cookie Walk
Cookies are set out on trays for guests to mix and match their own box of treats! - Saturday, December 14, 2024
9:00 am until cookies are gone
Jerusalem Presbyterian Church
2017 Main Street, Wales, WI
Doors open at 8:00 am, when numbers will be given out to hold your place in line. The church will sell fresh cinnamon rolls and coffee while you wait for the sale to start.
For more information, call Jerusalem Presbyterian Church at 262-968-3408. To reach the church, take I-94 to the Highway 83 exit and proceed south to Main Street in Wales. - Saturday, December 14, 2024
9:00 am until 11:00 am or cookies are gone
St. John’s United Church of Christ
N67 W28321 Sussex Road, Merton, WI
Homemade cookies will be available.
For more information, call: 262-538-1912.
We also recommend popping over to our SHOP SMALL GUIDE and hitting up these local YUMMY EATS retailers:
Sweet P’s Pantry in Oconomowoc
E and S Sweets in Mukwonago
All the Crumbs Cookies in Genesee
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
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 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
Walking the Ingleside Christmas lights. We drove them in years past. Experienced the walking part last year, AMAZING
It is a family tradition to drive through the Country Christmas lights at the Ingleside every year with the family. I am looking forward to walking them this year.
We walked through the Christmas lights today, our first time! Can’t wait to make it an annual tradition!
We took our 1 year old and he loved it! New family tradition!
Thank you for all these resources!! Love the info on the tree farms, lighting displays, Christmas markets & more! Always need reminders for these fun events!!
Magical! Can’t wait for the holidays. All the prizes look great but the Rudolph show would be so fun!