The cork is popping on our 10th Annual Wine Walk presented by Johnsonville, and we don't want you to miss out! Join us on September 10th for an unforgettable evening of wine, delicious snacks, local shopping, and a celebration of 10 amazing years of Wine Walk fun. Gather your friends, stroll through your favorite shops, discover new favorites, and raise a glass with fellow wine lovers along the way.
Don't miss this milestone event! Secure your tickets today before they're gone. ?✨
Check out the details below or in our Calendar of Events. Look forward to our upcoming events!
10th Annual Wine Walk Downtown Watertown September 10th
Celebrate a milestone year at the 10th Annual Downtown Watertown Wine Walk as we toast to A Diamond Night Downtown. Join friends, neighbors, and fellow wine lovers for an evening of sipping, shopping, and shining as downtown Watertown celebrates a decade of this beloved event.
Business After Hours Hosted By Habitat For Humanity September 17th
Enjoy an evening of great conversations, delicious refreshments, and fantastic opportunities to grow your business network. Don’t forget to bring your business cards.
Wake Up Watertown At Ready 2 Dance October 7th at 7:45 AM
Save the date for a morning of networking, connection, and highlights from Manufacturing Month.
Lunch & Learn Watertown Public Library October 8th
Join us for an insightful Lunch & Learn presented by KD InteractiveHostedBusiness Services. Discover how to improve your visibility on Google, attract more customers online, and leverage the power of artificial intelligence to work smarter, market more effectively, and stay ahead of the competition.
The WHS Gosling Alumni Giving Fund was created to support “the kid in the middle” – a graduating Gosling who may not have the highest GPA or the greatest financial need, but who shows up every day with consistent effort, service, character, and promise. Founded by alumni from the Watertown High School Class of 1984.
Jump Street Party Rentals is the go-to source for inflatable and party rentals, dedicated to delivering exceptional service, outstanding value, and unforgettable event experiences. Known for providing the best “bounce for your buck,” the company focuses on creating fun, stress-free events while ensuring every customer receives reliable, professional service.
Lake Country K9 to 5 is a Watertown Wisconsin-based pet care business that provides professional, dependable, and compassionate services for dogs and their owners.
Loos Homes builds new construction homes in Jefferson County and across Southeastern Wisconsin, all backed by third-party testing and transferable warranties.
Martin Real Estate is a family-owned, full-service real estate company with nearly 50 years of experience, offering comprehensive marketing and sales services with a competitive low commission rate of just 2.4%
River City Heating & Cooling 920-941-8025 Facebook
River City Heating & Cooling proudly serves the local community with reliable, professional heating and cooling services.
Since 2020, S Five Vision Media has become one of Watertown's premier photography studios, specializing in senior portraits, athlete branding, and entrepreneur photography.
Watertown Tourism
Watertown Tourism
Businesses & Organizations Wanted! Join us for Watertown Trunk-or-Treat on October 10! Participation is free, and participating businesses and organizations are asked to provide candy and/or handouts to trick-or-treaters. With more than 1,000 trick-or-treaters expected, it’s a great opportunity to connect with families and show off your organization.
Join us at Lyons Irish Pub on September 16 for the Art on Main LIVE Auction, where the banners that have been proudly displayed along Main Street all summer will be auctioned off to the highest bidders.
Come early at 5:30 PM to preview the banners, choose your favorites, and enjoy an evening celebrating local art, talented artists, and Downtown Watertown. The LIVE Auction begins at 6:30 PM.
Registration Open Now!
We’re excited to invite you to participate in our Women’s Only Weekend Swag Bags! This is a fantastic opportunity to showcase your business and connect with a vibrant community of women. By contributing promotional items, samples, or special offers, you’ll help create a memorable experience that celebrates, supports, and empowers women throughout our community.
Raffle Donation & Swag Bag items: All raffle donations and swag bag items must be dropped off at the Main Street Program office, 519 E Main St., no later than November 6, 2026.
HelpMakeWitches'BrewBingoaSpooktacularSuccess!
The Watertown Main Street Program is seeking raffle baskets, gift cards, and prize donations from local businesses for the upcoming Witches' Brew Bingo fundraiser. Your donation will help raise funds for the Main Street Grant Program, supporting improvements to Downtown Watertown businesses. It's a great way to showcase your business while supporting a vibrant downtown community. Thank you for your support!
If you have any questions, please reach out to Stefanie.
Redevelopment Authority\'s (RDA) Citywide Sign Grant Program
The Redevelopment Authority (RDA) of the City of Watertown continues to support local business investment through its Citywide Sign Grant Program. The program provides eligible businesses with a 50% matching grant, up to $1,000, to assist with permanent exterior signage improvements that enhance visibility and strengthen the community’s commercial corridors. Eligible signs must be permanently installed, visible from a public street, and either mounted to a building exterior or incorporated into a monument sign. Businesses should note that all projects require RDA Board approval before any on-site work begins, and grant funds are reimbursed upon submission of a paid invoice. Businesses located within the City’s downtown historic district are not eligible for this program and are encouraged to explore sign and façade grant opportunities available through the Watertown Main Street Program.
Chamber member Ready 2 Dance was recently awarded a sign grant through the Redevelopment Authority's (RDA) Citywide Sign Grant Program.
Chamber Member Promotions & Events
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Watertown Area Chamber of Commerce
National Technical Honors Society Support the Future Workforce
We are currently seeking sponsors and guest speakers to support the National Technical Honor Society as we relaunch the program and expand opportunities for deserving students. Contributions help cover membership dues, ceremonies, graduation regalia, and industry engagement experiences, while guest speakers can inspire and guide students as they prepare for future careers.
By volunteering as a Big Brother or Big Sister you have the opportunity to impact the life of a child for the better. Together, we are Defenders of Potential!
We’re always looking for people eager to positively impact a child and improve their community at the same time. For a few hours a month you can give a child the invaluable gift of your friendship. By simply changing their perspective of what the world can offer, you can literally start changing their life! It’s as simple as playing catch, going to a ball game, painting nails, watching a movie, sharing stories, and just hanging out together!
WBR’s new Dance Birthday Party Package offers two hours of studio fun with dance instruction, games, a group performance, and full setup support, creating a memorable celebration for just $150.
Going to be a memorable night with Tracey Ann Music filling the air with great music and Chef Chris Ghobrial filling the plates with amazing food.
Bcause We Care Meat Raffle September 5th at 12PM
Join us for a Meat Raffle! All proceeds benefit Because We Care, helping support our community and those in need.
Watertown Daily Times Annual City Wide Rummage September 10-12
Get ready to hunt for bargains all across Watertown! From hidden treasures to everyday essentials, you never know what you’ll find.
Want your sale listed in the Watertown Daily Times?
For pricing and listing information, call 920-390-6040.
Watertown Family Connections Protective Factors Foundations Training September 10, 17th, October 1st, 8th, & 14th
This engaging training explores the Protective Factors Framework, a proven approach that helps strengthen families, support healthy child development, reduce stress, and lower the risk of child maltreatment.
Get ready for an afternoon bursting with flavor, music, and family fun! This free, family-friendly celebration brings people together to honor Hispanic heritage through delicious food, lively entertainment, cultural tradiƟons, and community connections.
Summer Vendor Market Madison's Crafts and Fabric September 12
Whether shoppers are looking for handmade gifts, unique finds, treats, home décor, art, accessories, or a fun Saturday outing, our goal is to create a welcoming market filled with variety, creativity, and local small-business energy.
Rainbow Community Care Brat Fry & Bake Sale September 12
Rainbow Community Care is partnering with Watertown Piggly Wiggly for a Brat Fry and Bake Sale!
The Score Sports Bar Tailgate Party September 13
Join us at The Score Sports Bar for the Packers’ FIRST REGULAR SEASON GAME as Green Bay takes on Minnesota!
Culver's Share Night Benefitting CCLS September 15
We are excited to share that CCLS is having a Culver’s Share Night on September 15th from 5:00-8:00pm in Watertown! Come enjoy a tasty meal or purchase a gift card to support CCLS and our clients with intellectual and developmental disabilities! Donate while you dine and help make our Culver’s Share Night a success!
EAA Chapter 320
Fly- In Food Fests Sept 16th
Come and gawk at some cool planes, cars, & motorcycles while fueling up on pulled pork and shredded turkey sandwiches!
Lyons Irish Pub Halfway to St. Patrick's September 18th
Daniel and Claire make up the duo, "the foxfire affair." These multi-instrumentalists bring a full band sound when playing multiple instruments simultaneously.
Join us for a ball park lunch and a guided tour of the space will be provided.
Leaving Iowa Watertown Players' Theatre September 25 & 26 at 7 PM September 26 & 27 at 2 PM
Tickets are now on sale for the Watertown Players' production of Leaving Iowa, a heartwarming comedy about family road trips and memories, with performances September 25-27 at the Watertown Players Theater and advance tickets available for $15 online or at Piggly Wiggly.
Gosling Alumni Leadership Forum October 1 Silver Moon Watertown
You’re invited to the Gosling Alumni Leadership Forum, an evening designed to bring WHS alumni from every era together to reconnect, share ideas, and explore how we can build a stronger alumni community for generations to come.
WHS Alumni Golf Outing Watertown Country Club October 3rd
We welcome you to join us for the 1st Annual Watertown Youth Golf Association (WYGA) Golf Outing, to support the Watertown High School (WHS) Golf Teams.
Watertown Concert Series Watertown High School October 3rd
Celebrate some of the greatest duos in entertainment history with this high-energy musical comedy revue. Audiences will enjoy memorable songs and stories featuring legendary partnerships from Johnny Cash & June Carter to Fred Astaire & Ginger Rogers, delivering an evening filled with music, laughter, and nostalgia.
Watertown Dementia Awareness Coalition A Day with Lewy Conference October 8th, 2026
Join us for a FREE informative conference dedicated to expanding your knowledge and comprehension of Lewy body dementia, exploring its impact, symptoms, and the latest research in the field.
Jefferson County Cancer Coalition Frosty Balls Golf Outing October 10th
When cancer impacts one of us, it impacts all of us. The Frosty Balls Golf Outing brings our community together to support neighbors navigating cancer right here in Jefferson County.
Beyond Pink: Class of 2026 honors eight local breast cancer survivors through an inspiring afternoon of storytelling, recognition, hope, and community.
Creative Community Living Services (CCLS) is hosting our annual Dueling Pianos Fundraiser on October 24th in Oconomowoc at Cornerstone Pub & Eatery. Get ready for a night of fun with performers Howl2GO!
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