Trunk or Treat at Generations
2025-10-05 13:00 - 15:00 (America/Chicago) | Generations Intergenerational Center, 1500 Douglas Drive, Plymouth, WI, 53073, United States
Trunk or Treat is at Generations on Sunday at Generations from 1-3. Trick or treating from car to car. Music and crafts and treats.

Fall Harvest Days
2025-10-10 09:00 - 2025-10-12 17:00 | Rumley Acres, W1545 County Rd MM, Cleveland, WI, 53015, United States
Fall Harvest Days at Rumley Acres in Cleveland Friday-Sunday. Food,
kids activites, music, demos, and antique equipment. Open at 9 each day.

Plymouth Fire Department Open House
2025-10-10 17:00 - 20:00 | Plymouth Fire Station, 111 East Main Street, Plymouth, WI, 53073

Paint the Towns in Fall Color
2025-10-10 18:00 - 21:00 | Plymouth Arts Center, 520 East Mill Street, Plymouth, WI, 53073
Plymouth Arts Center to Host Public Reception
For Paint the Towns in Fall Color

The public is invited to a festive reception and silent auction on Friday, October 10, 2025, from 6 pm to 9 pm to view the paintings created at this year’s Paint the Towns in Fall Color event. It is a great opportunity to meet the participating Paint the Towns Artists and to bid on your favorite piece of Sheboygan County art at the Silent Auction until 9:00 pm. Awards will be presented at 6:45 pm. After the reception and silent auction, the unsold works will remain in Gallery 110 North through November 14 and be for sale at a “Buy it Now” retail price. This free admission reception features live music by Zach Holzer, complimentary appetizers, and desserts, along with a cash bar. The event sponsors are Sargento, Masters Gallery, Plymouth Furniture, and Barbara and Conrad Barrows with supporting sponsorship from Pleasant View Realty, Kenjay Fiedler Excavating, Inc., Roadside Bar & Grill, Allechant Boutique, Racer’s Hall, and Suchon Funeral Home. All proceeds of this event benefit the Plymouth Arts Center, a charitable 501c3 non-profit organization.

Midwest artists who are interested in participating in this annual en Plein Air (outdoor painting) competition and exhibition, coordinated by artist Dan Rizzi, may visit or call the Plymouth Arts Center, 920.892.8409. Pre-registration is encouraged. A total of $3000 in cash awards will be presented. A full schedule of events may be found on the PAC website: www.PlymouthArts.Org and Facebook page. Plymouth Arts Center is located at 520 E. Mill Street, in beautiful downtown Plymouth, Wisconsin.

The Plymouth Arts Center is a 501(c)3 charitable non-profit organization solely supported through memberships, fundraisers, business and individual donations, grants and sponsorships. The mission of the PAC is….to enliven the spirit of our community and to enrich the lives of all, by providing diverse experiences in the arts.

Cascade First Responders Meat Raffle
2025-10-11 12:00 - 16:00 | Sipp’s Bar N Grill, 507 Madison Ave., Cascade, WI, 53011, United States
Join the Cascade First Responders for our 3rd Annual Meat Raffle, hosted at Sipp’s Bar-n.-Grill, located at 507 Madison Avenue in Cascade! We will be raffling off baskets stocked with meat, cheese, and goodies throughout the entire duration of the meat raffle! All proceeds from this event directly benefit the Cascade First Responders, specifically to purchase medical supplies essential for our EMS calls, as well as to support the education and skill development of our first responders.
If you would like to make a cash donation to the meat raffle or are interested in donating items, please contact Kim Kuehl at 704-281-4482 or meetkimhughes@gmail.com.
There is an ATM on site. Food and refreshments will be available for purchase at Sipps during the event.
Stay after the Meat Raffle and enjoy karaoke and Shy Guys DJ to celebrate the end of the Highway 28 road construction through Cascade… FINALLY!

National Cheese Curd Day
2025-10-15 08:00 - 22:00
On October 15, National Cheese Curd Day celebrates the velvety goodness of cheese curds. This delicious food holiday allows us to indulge in the unique, funky, snackable little pieces of yellow or white Wisconsin cheddar cheese. Did we mention they are also deep fried?
#NationalCheeseCurdDay
Cheese Curds are one of the most unique appetizer items you can eat. One bite brings you straight to a warm buttery crunch, followed by an ooey-gooey burst of dairyland delicacy on the inside. Made with unaged, curdled milk with a mild, salty flavor and a springy, rubbery texture, cheese curds are known for the “squeak” they make when you bite into them. They are a natural byproduct of the cheesemaking process, most commonly cheddar.
NATIONAL CHEESE CURD HISTORY
Culver’s founded National Cheese Curd Day in 2015 to celebrate the delicious and snackable treat.

Plymouth Farmer's Market
2025-10-16 15:00 - 18:00 | Stayer Park, 39 Stafford St, Plymouth, WI, 53073, United States
The Plymouth Farmer’s Market at Stayer park!

Ladies Nite Out in Sheboygan Falls
2025-10-16 17:00 - 19:00 | downtown Sheboygan Falls, Sheboygan Falls, WI, 53085, United States
Ladies Nite Out in Sheboygan Falls is Thursday in Sheboygan Falls at 5.

Track and Treat
2025-10-18 13:30 - 16:30 | Road America, N7390 Hwy 67, Plymouth, WI, 53073, United States
Track and Treat at Road America on Saturday from 1:30 to 4:30. Enter at gate4.

2025 Sheboygan Caregiver Conference
2025-10-20 08:30 - 15:00 | Sheboygan Lutheran High School, 3323 University Dr., Sheboygan, WI, United States

Sheboygan Farmer's Market
2025-10-22 08:00 - 13:00, 2025-10-25 08:00 - 13:00 | Fountain Park, 8th St. & Erie Avenue, Sheboygan, WI, 53081, United States
The SCIO Farmers Market makes available fresh, native products directly from farmers to residents. It works to help local farmers remain vibrant, educate the community on healthy eating, and provide a social experience that helps build community. Did we mention the flowers? Truly the best selection of fresh cut flowers in the county is at the Farmers Market.

Trunk or Treat Plymouth
2025-10-24 17:00 - 19:00 | Fairfield Plaza, 2112 Eastern Ave, Plymouth, WI, 53073, United States

Improv Comedy Shows
2025-10-24 19:30 - 2025-10-26 21:30 | Plymouth Arts Center, 520 East Mill Street, Plymouth, WI, 53073

Trick or Treat for the kids at Sheboygan Senior Community
2025-10-25 13:30 - 15:00 | Sheboygan Senior Community, 3505 Co Rd Y, Sheboygan, WI, 53083, United States
Trick or Treat for the kids at Sheboygan Senior Community on County Road Y in Sheboygan Saturday from 1:30-3.

Trick or Treat Hours
2025-10-25 15:00 - 19:00
Trick or Treat hours Saturday October 25th
Adell 3-5 p.m.
Cascade 3-6 p.m.
Waldo 4-7 p.m.

Waldo Lions Halloween Roller Skating Party
2025-10-25 18:00 - 20:30 | Waldo Memorial Hall, 308 West First Street, Waldo, WI, 53093, United States
Waldo Lions Halloween Roller Skating Party
When: October 25th 6pm-8:30pm
Where: Waldo Memorial Hall
We will be offering Pizza, Roller Skating, Music and Prizes

Glow Hike at Maywood Environmental Park
2025-10-25 18:30 - 21:00 | Maywood Environmental Park, 3615 Mueller Road, Sheboygan, 53083, United States
Follow colorful luminaries along trails through Maywood Park and experience the park in a new light! First 100 pre-registered participants will receive an eco-friendly reusable glow stick to enhance the evening under the stars. Enjoy a self-guided 3/4 mile multi-color luminary-lit trail, followed by glow-in-the-dark games and activities with music and more colorful lighting!
The event will feature a cosmic glowing beer garden area for adults. Snacks, beverages, and additional glow items will be available for sale at the event.
Please dress appropriately for the weather, as the event will take place outdoors.
$7/Maywood Association Member
$10 /General Public

Cascade Lions Soup-A-Rama
2025-10-26 10:00 - 14:00 | Cascade Lion Hall, 303 W. Water St., Cascade, WI, 53011, United States
The Cascade Lions Club welcomes you to join us at the Cascade Lions Hall for our Annual Soup-A-Rama! We will be serving over ten kinds of soup (more details to come on the exact soups), grilled cheese, and assortment of desserts for this all you can eat event. $10 for adults, $5 for kids under 10 years old. As always we will have drinks and walk around raffle prizes available with a money tree to also be raffled off (need not to be present at the time of the drawing to win the money tree). This will run from 10:00 am – 2:00 pm (or until sold out).

Plymouth Trunk or Treat
2025-10-26 13:00 - 15:00 | Stayer Park, 39 Stafford St, Plymouth, WI, 53073, United States
October 26
1:00 PM – 3:00 PM
Stayer Park – 39 S Stafford St.
The American Legion Family, Ladewig-Zinkgraf, Post 243 will be sponsoring the Trunk or Treat before the City Trick or Treating at Stayer Park.

Plymouth Trick or Treat
2025-10-26 15:00 - 17:00 | Plymouth, Plymouth, WI, 53073, United States

Trick or Treat Hours
2025-10-26 15:00 - 17:00
Sunday, October 26
Cleveland 4-6 p.m.
Elkhart Lake: 3–5 p.m.
Plymouth: 3–5 p.m.
Random Lake: 3–5 p.m

Great Pumpkin Pageant
2025-10-28 08:00 - 2025-10-31 17:00 | Plymouth Public Library, 130 Division St., Plymouth, WI, 53073, United States
Plymouth Public Library’s 5th Annual Great Pumpkin Pageant!
Monday, October 27th through Friday, October 31st 2025!
Here’s how to participate:
Buy a pumpkin.
Decorate it and make it book inspired! NO CARVED PUMPKINS, just use glue and paint!
Drop off your pumpkins on Monday, October 27th to go on display at the library.
Starting Tuesday, October 28th, come into the library and vote for your favorite pumpkin —the one with the most votes gets a prize!
Pumpkins will be on display through Friday, October 31st. You can pick up your pumpkin to take home on Friday, otherwise they will be discarded.
If you’d like to participate without bringing your pumpkin to the library, be sure to tag us on social media and use the hashtag #PPLPumpkinPageant so we can see your pumpkins!
Any questions can be directed to the Youth Services Librarian, Miss Sam.

Sheboygan's Haunted Asylum
2025-10-30 18:30 - 2025-11-02 22:30 | Sheboygan Asylum, N3773 Garden Parkway, Sheboygan Falls, WI, 53085, United States

"Our Town" at PHS
2025-10-30 19:00 - 2025-11-02 16:00 | Plymouth Comprehensive High School, 125 S Highland Ave, Plymouth, WI, 53073, United States
“Our Town” will be presented by the Plymouth High School Drama Department at 7pm Thursday-
Saturday (30th -November 1st) and at 2pm on Sunday afternoon 11/2 in the Plymouth High
School Auditorium.

Trick or Treat Hours
2025-10-31 16:00 - 19:00
Friday, October 31 (Halloween Day)
City of Sheboygan: 4–7 p.m.
Cedar Grove: 4–7 p.m.
Glenbeulah: 6-8 p.m.
Howards Grove: 4–7 p.m.
Kohler: 5-7 p.m.
Oostburg: 4-7 p.m.
Sheboygan Falls: 4-7 p.m.

Plymouth Pumpkin Walk
2025-10-31 17:00 - 19:00 | Stayer Park, 39 Stafford St, Plymouth, WI, 53073, United States

Halloween Sock Hop
2025-10-31 19:30 - 22:30 | Plymouth Arts Center, 520 East Mill Street, Plymouth, WI, 53073
Halloween Sock Hop on Friday at the Plymouth Arts Center from 7:30 to 10:30.

The American Cancer Society Run/Walk
2025-11-01 08:00 - 11:30 | Road America, N7390 Hwy 67, Plymouth, WI, 53073, United States
The American Cancer Society Run/Walk is at Road America on Saturday morning. Find more info at: https://runsignup.com/Race/WI/Plymouth/RoadAmericaWalkRun

Holiday Craft Fair
2025-11-01 08:30 - 14:00 | Saint John Lutheran Church, 222 N Stafford St, Plymouth, WI, 53073, United States
Saint John Lutheran Church and School in Plymouth is having their Annual Holiday Craft Fair on
Saturday, November 1st from 8:30 to 2. It’s a 100% handmade show.
