Top 10 Reasons You Should Visit Watertown, WI

Published On: Friday, October 11, 2019By Categories: Blog, Special FeaturesTags: , , , , ,
Pictures of events in Watertown Wisconsin

Enjoy family friendly events in Watertown, WI!


Watertown, Wisconsin is full of activities and amenities to enjoy in the final months of 2019.  We’ll take out the guess work and give you our top 10 reasons to explore this historic city!

#10 Historic Walking Tours

Watertown has five nationally registered historic districts, which can be enjoyed by picking up a walking/driving tour brochure.  The mild fall weather is the perfect time to stroll through the districts, learning more about early settlers, historic Main Street, Watertown’s brewery history, and so much more.  Pickup a Brochure at the Watertown Area Chamber of Commerce or download the Historic Walking Tour Guide from the Watertown Chamber’s Website.

#9 Pumpkin Palooza

Pumpkin Palooza, held in historic downtown Watertown gives you all the feels of fall, with horse-drawn wagon rides, sidewalk games, face painting, and Main Street Trick-or-Treating, and more.  Our favorite part?  The costumes!  Family-themed costumes, adults, children, and even pets get in the spirit.  We promise, you’ll be impressed.  October 26, 2019 – activities run from 10 a.m. until 3 p.m., with the very popular Main Street Trick-or-Treat set for 1-3 p.m. at participating businesses.

#8 Fall Foliage-Enjoy it on the River!

It’s a beautiful time of year to enjoy the sights and smells of fall.  But have you ever done it from the river?  The Tree-lined Rock River winds through Watertown and just might be the best “highway” to experience the fall foliage.  Map for the Put In/Take Out sites in Jefferson County.

#7 Craft Fairs

This community knows how to put on a craft fair, and there are several to enjoy.  November 1st– Marquardt Village Holiday Craft & Gift Fair, 1045 Hill St.  November 2nd – MBU Craft and Gift Fair, 745 W. Main St. November 24th – Turner Hall Craft Fair, 301 S. Fourth St.  The Turner Hall Craft Fair has been running for nearly 4-decades and includes 2-floors of quality craft and artisan items.  Plan on getting your Christmas shopping done at this event!

#6 Octagon House Annual Christmas Play

Not only do you get to experience the Octagon House Museum, but you get to enjoy a holiday play in the historic home.  This year’s play is The Gift of the Magi.  Each scene of the show takes place in the four main rooms on the first level of the Octagon House Museum. The actors will lead the audience through the show, and afterwards those attending will be invited to enjoy holiday treats. The show will be presented on November 30th and December 1st, from 11:00 to 3:00 each day, with a new performance approximately every 30 minutes throughout the day.  Tickets are available at the event on the day of the show at 919 Charles St.

#5 Watertown Window Wonderland

This event grows every year.  Watertown has one of the largest Main Streets in Wisconsin, with nine blocks of store-fronts!  Beginning on Thanksgiving weekend, participating store owners elaborately decorate their store-front windows for the holidays in order to win the public’s vote for best holiday window.  The store owners’ competitiveness is a big win for the community, as the city streets glow throughout the season.  Pick up a ballot at any participating business and stroll the downtown, choosing your first, second, and third favorite window.  The contest runs from December 1-December 15, with windows remaining decorated through New Year’s.

#4 Christmas Parade of Lights

This after-dark parade ushers in the holiday season.  You’ll enjoy live bands, unique parade units, dancers, stilt walkers, and lots and lots of lights!  Don’t forget to bring an empty bag to catch all of the candy and handouts.  The parade runs in historic downtown Watertown on November 30, 2019, and starts at 5:30pm.  Visit Santa in his house after the parade in the downtown plaza (read below).

#3 Santa House

Did you know that Santa has a beautiful home in Watertown, located in the downtown plaza during the holiday season?  Santa House is open for visits according to the schedule below in 2019.  The house is wheelchair accessible so every child has an opportunity to visit with their Christmas wish list.  Please note that these dates/times are subject to change due to weather conditions.  2019 hours:

  • Nov 30, 7-8 pm
  • Dec 5, 6-8 pm
  • Dec 7, 2-4 pm
  • Dec 9, 3-5 pm
  • Dec 10, 6-8 pm
  • Dec 12, 4-6 pm
  • Dec 15, 6-8 pm
  • Dec 18, 6-8 pm

#2 Seasonal Ice Cream

Your love of ice cream doesn’t go away when the temperatures go down, and Mullen’s Dairy Bar completely understands!  Their lineup of homemade ice cream flavors brings customers from all over the country, and their seasonal flavors can’t be beat. How about some pumpkin, caramel apple pie, or chai flavor?  You bet!  But you have to be quick, because their seasonal flavors are just that – seasonal.  Mullen’s Dairy Bar is located at 212 W. Main Street.

#1 CP Holiday Train

The Canadian Pacific Holiday Train rolls through communities in U.S. and Canada during the holiday season, brightly decorated with lights galore.  The train stops in several communities along the way, and Watertown has been chosen as a stop year after year.  One boxcar is turned into a traveling stage, and it opens up to entertain the crowd with a live band performing a 30-minute set of lively holiday music.  The free event acts as a fundraiser for local food banks and attendees are encouraged to bring non-perishable food items to donate.  December 3, 2019, Brandt-Quirk Park (time and additional details TBD.  Follow Watertown Tourism on Facebook for updates).

Robin Kaufmann is the Tourism Manager for the city of Watertown. She eats, sleeps, and breathes travel in her personal and professional life. She is the voice of Watertown Tourism, and the Facebook specialist for Enjoy Jefferson County Tourism.

Please follow & like us :)

April Contest Winner Larry K from Wauwatosa

Recent Posts

Take a Jefferson County Road Trip – 1950’s Style
Take a Jefferson County Road Trip – 1950’s Style
Take a step back in time on this Jefferson County Road Trip! We’re sharing all the best diners, old-fashioned ice...
Memorial Day Weekend Fun Around Jefferson County
Memorial Day Weekend Fun Around Jefferson County
Hello, warm weather, and yay for a holiday weekend we love spending outside! Aside from the beloved backyard BBQ, this...
The Pottery Scene in Cambridge
The Pottery Scene in Cambridge
The arts thrive in Jefferson County and Discover Wisconsin visited to learn more about our arts history and culture.
Watertown Has an Impressive Event Season Planned
Watertown Has an Impressive Event Season Planned
Watertown’s calendar is packed with exciting events in 2022. Music, markets, fun runs, comedy shows, and more. This list continues...
Celebrate Love at The Fort Atkinson Club
Celebrate Love at The Fort Atkinson Club
Jefferson County is home to some of the most beautiful, unique, affordable, and conveniently located event venues in Wisconsin. Join...


By submitting this form, you are consenting to receive marketing emails from: Jefferson County Tourism Council, PO Box 243, Jefferson, WI, 53549, You can revoke your consent to receive emails at any time by using the SafeUnsubscribe® link, found at the bottom of every email. Emails are serviced by Constant Contact