Oconomowoc's storefronts are getting festive and the lights are being strung on the trees! Make sure you don't miss any of our favorite events! From now to Thanksgiving, Christmas and New Year's, we've got fun things ahead!
Friday, Nov. 21 - Harvest Wine Walk
5-8pm: It's a late fall downtown shopping event! Perfect timing for checking some names off your list, or grabbing some things for yourself. Grab your friends and spend the evening in downtown Oconomowoc as stores stay open late, host special sales and are stocked with drinks and treats to keep you going. Plan dinner out downtown while you're here.
Oconomowoc's German Christmas Market
Thanksgiving weekend isn't just about stuffing and turkey in Oconomowoc. It means the Oconomowoc German Christmas market is here!
5-10pm Wednesday, Nov. 26
It's Thanksgiving Eve and the market grounds get a little warmup when the Entertainment tent opens for music and merriment. Doors open at 5pm, David Graham & the Eskimo Brothers will play starting at 6:30pm. Wednesday evening will also have the traditional keg tapping. Beer part of the fun!
10am to 10pm Friday, Nov. 28
The first day of the 2025 market! The full market opens at 10 am full of vendors, the polka music will start, Santa will take his seat and the smells, oh the smells of all the delicious treats will waft through the air! *please note vendor huts close at 8pm Friday and Saturday but the tent keeps rocking until 10pm.
10am to 10pm, Saturday, Nov. 29
Market continues Saturday. Looking to make sure you don't miss Santa? Here's his schedule on the market's website, oh and some reindeer visit Saturday evening!
10am to 4pm Sunday, Nov. 30
Final day of the market and things wrap up at 4pm. Make sure you don't miss out, or plan your second, or third trip before it's gone for the season!
The market is offering free shuttle service! Avoid the hassle of finding parking downtown. You can find details on the shuttle as well as all things Oconomowoc German Christmas Market on their amazing website!
Letters to Santa - Dec. 1-15
Santa's mailbox will return in front of City Hall. The Friends of Oconomowoc Parks & Trails put out the Santa Letter Box for all the children to write their Christmas wish letters, to Santa. The Santa Box will be out in front of City Hall, 174 East Wisconsin Avenue, near the front entrance.
The box will be put out Dec. 1 and remain until Dec 15. Santa will answer every letter he receives in his special mailbox.
Christmas Tree Lighting Ceremony, 4:30pm, Sat., Dec. 6
The official City Christmas tree will light up shortly before the annual Christmas parade the evening of Saturday, Dec. 6. Grab a cup of hot cocoa courtesy of St. Matthew's Church and gather around the City Christmas tree. The Oconomowoc Community Choir will sing Christmas carols in front of the tree and Mayor Robert Magnus will join as we all count down to light the tree right before the Christmas parade begins at 5pm.
Oconomowoc's Christmas Parade, 5pm, Sat., Dec. 6
The Oconomowoc Kiwanis Club organizes a sparkling stream of floats, marching groups and more for its annual Christmas Parade. The nighttime lighted parade begins at 5pm just north of the roundabout.
The parade begins just north of the roundabout at Walnut/Pleasant streets. It travels through the roundabout and west on Wisconsin Avenue. It then turns right on North Main Street and ends at the intersection of North Lake/Lisbon Road. Don't forget to bring donations for the Oconomowoc Food Pantry and children, make sure you have your letters to Santa ready. Elves will be in the parade to collect them. All letters will receive a response.
Christmas on the Isthmus - 4-7pm, Saturday, Dec. 6
Following the Christmas Parade, head to North Lake Road downtown - Oconomowoc's isthmu for the 5th annual Christmas on the Isthmus!
The event is held by neighbors on historic Lake Road in Oconomowoc on the isthmus between Fowler Lake and Lac La Belle. This year’s event will again benefit the Lake Area Free Clinic and will be held before, during and after the Christmas parade on December 6th from 4-7 PM. Families will have a chance to stroll down Lake Road and enjoy and old-fashioned Christmas. Walk in the historic neighborhood and see homes beautifully decorated for Christmas, enjoy the treats and drinks offered by participating homes, visit with Santa and enjoy Christmas music.
Donations can be made to the Lake Area Free Clinic at each participating home. With the help of community donations, the Lake Area Free Clinic has been providing life-changing medical, dental and referral services to residents of Waukesha County since 2001 who lack health insurance and the ability to pay for health care.
-Visit with Santa on the porch (don’t forget your letters for Santa!)
-Enjoy treats in the neighborhood
-Pictures with a Hallmark truck
Look for signage in front of house participants.
Holiday Train - 6:40 p.m., Wednesday, Dec. 10
Experience the magic of a 1,000-foot lighted train that opens up to feature a live band playing Christmas music! The Holiday Train rolls in the Christmastime magic to Oconomowoc. The train stops at the Silver Lake Street rail crossing in downtown Oconomowoc. Since its inception, the Holiday Train has raised more than $26 million and 5 million pounds of food donations for local pantries. Oconomowoc's Holiday Train is a seasonal blessing to the Oconomowoc Area Food Pantry that supports our greater community.
Grab your pantry donations and head out early to enjoy caroling about a half hour before the train's arrival. St. Matthew's mission team will be on site offering cocoa and cookies for donations to support their missions.
Grab a great spot and enjoy the show! The train is anticipated to arrive at approximately 6:40pm. The band will play about 45 minutes on both the north and south sides of the tracks, it's quite the experience!
Noon Year's Eve - 10:30am-12pm, Wednesday, Dec. 31
Start your New Year's celebrations off on the right foot or two! Back for its fifth year, Noon Year's Eve is the best family friendly, Oconomowoc only tradition!
New this year, the event is moving to Meadowview Elementary School, 1500 Whalen Drive. AND an adults 5k has been added to the fun. Why do the kids get to have all the fun running into the New Year? No more, our friends at Silver Circle Sports events have added a race through the adjacent neighborhood. Run, walk, roll, stroll on this course. You can enjoy a 5K run or 1.5 mile walk. The point is to get moving and enjoy some fresh air.
And don't worry, the free kiddos 1K is still in the mix. Sign up to make sure we have all the race bibs and medals we need!
After the race enjoy hot cocoa inside Meadowview's common area, dance to tunes and enjoy a photo opps and some free goodies inside the gym. Then head out front before Noon to get raedy for the ball drop thanks to our friends at Western Lakes Fire District and their giant ladder truck! We plan to have another cool touch a truck option that day as well. Make sure Noon Year's is on your holiday calendar!
