"We are rolling pumpkins down the hill!" That's the pitch on Nutt Hill's homepage for Saturday, October 17, and it's the first time the hill at 750 W. Main St. has thrown a party to cover its own operating costs. Cheese Capital Winter Park, the nonprofit that runs Nutt Hill, calls Squirrel Fest its first annual fundraiser. The Sheboygan Press reported that proceeds will help the hill keep offering affordable winter activities.
Before the rebuild, donors covered capital costs like snowmaking, a lift and buildings. This October is the first time the hill is asking for help with the day-to-day work of staying open. Plymouth residents paid to bring Nutt Hill back. Whether its second winter goes well depends on the same people, and the ask now comes with a barbecue and a pumpkin roll.
What happens on the hill October 17
Admission is free from noon to 6 p.m. You only need a ticket for the wine-and-cheese pairing. Here's the afternoon:
- Acorn Scavenger Hunt, noon to 1 p.m. It's free and works like an Easter egg hunt, with big acorns hidden on the slope. There are two age groups, 4 to 6 and 7 to 10, with up to 50 kids in each.
- BBQ, noon to 6 p.m. Food is for sale on site: pulled pork, steak sandwiches, award-winning mac-n-cheese, German potato salad, desserts, beer and soda.
- DJ Jimmy James, 1 to 6 p.m. Free.
- Pumpkin Rolling Contest, 1 to 6 p.m. Pumpkins are for sale at the hill. One of the prizes is a ski and snowboard season pass.
- 50/50 Raffle and Gift Baskets, 1 to 6 p.m. Tickets are sold on site.
- Wine & Cheese Pairing, 1 to 5 p.m. Presale tickets are $35 for five fall wines matched with cheeses from Wisconsin cheese companies.
The season pass prize gives the best pumpkin rollers something they can use in a few weeks. Families who'd buy a pass anyway get a cheap shot at a free one.
Why the hill needed a nonprofit at all
Nutt Hill has a longer history than most people in town know. The nonprofit's own timeline says Drs. Charles and Genivera Nutt acquired the property in 1946. The community established the hill in 1962, and the city bought snowmaking equipment in 1969. For decades it ran as city park winter recreation, with a rope tow, snowmaking and lights for night skiing.
The hill went dark for more than a decade. Sources disagree on exactly when it stopped. A 2025 Sheboygan Press story puts the closure in 2011. Seehafer News reported that organized winter recreation hadn't happened since February 2014, and the nonprofit's timeline also marks 2014 as the year the hill became inoperable. Joe Van Derven, Cheese Capital Winter Park's president during the revival effort, said the city eventually couldn't put enough resources into maintaining it.
That's how a small group of Plymouth residents ended up forming a nonprofit to raise money and rehabilitate a property the city owns. In November 2024 the Plymouth Common Council voted unanimously to give Cheese Capital Winter Park a five-year operating license, with up to three more renewal terms. Some coverage said the nonprofit "purchased" the hill, but it didn't. The city still owns the land, and the nonprofit runs the hill under that license.
This setup is why Squirrel Fest matters. A city department has a budget line. A nonprofit operating under a license has whatever it raises plus whatever it brings in from tickets.
What $2.3 million of community money bought
According to the nonprofit, community donations to revitalize the hill have passed $2.3 million. Most of that money went into things visitors never notice until they fail:
- Snowmaking. The hill's snowmaking equipment dated to 1969. New equipment went in during 2025, including a new pump station, new piping, hookups for two portable snowmakers, and a fixed snowmaker on the tubing hill.
- Grooming. The hill bought a PistenBully 100 groomer.
- Lift. A conveyor lift replaced the old rope tow, which makes the climb easier for tubers and beginners.
- Buildings. The original warming lodge was upgraded, and a second building was added.
- Terrain. The slope was regraded in places for better snow coverage and flow, and a new ski and snowboard run was added in 2025.
The board also hired someone who knows snow. Brandon Malley became general manager in 2025, and the nonprofit cited his 11 years of experience in snowmaking and winter-sports instruction. Asher Spatz of Elkhart Lake won the contest to name all three ski runs.
Nutt Hill reopened for tubing, skiing and snowboarding on December 16, 2025, and Van Derven spoke at the reopening.
What the first winter showed
Less than three weeks after opening, the hill closed temporarily on Monday, January 5, 2026. The Plymouth Review reported that the team posted on Facebook that it was listening to feedback and working on problems with the tubing lanes after hearing from community members. The season went on, and WHBL reported in early March that it would end March 15.
The tubing lanes are still the part of the hill that's changing. Public plans from fall 2024 called for six tubing lanes. The homepage now lists three to four tubing lanes and two ski and snowboard runs. If you went last winter with a picture of the original plan in your head, that's what you'll find now.
Even the first-season pause shows how this hill works. When tubers raised concerns, the response was a public post and a fix. Nobody sent a complaint through a city department. The people steering the hill are the same people riding it, and October's fundraiser runs the same way.
Season two, by the numbers so far
The website says it's getting ready for the 2026-2027 season. Here's what the online store lists as of early October:
| Product | Price | Per-unit math |
|---|---|---|
| 26-27 Individual Ski/Snowboard Season Pass | $150 | One rider |
| 26-27 Family Season Pass, 4 or more | $500 | $100 less than four individual passes |
| Tubing 5-pack | $80 | $16 per ticket |
| Tubing 20-pack | $300 | $15 per ticket |
The season passes are labeled 26-27. The tubing packs carry no season label, so check with the hill before you count on them for this winter.
A family of four skiers comes out ahead on the family pass. A family of five or six saves more, since the $500 price covers four or more people. If you mostly tube, the 20-pack drops the price by one dollar a ticket compared with the 5-pack.
Some details haven't been posted yet. As of October 4, the site lists no 2026-27 opening date, daily hours, single-day ticket price, lesson schedule or dated event calendar. Last season WHBL reported that the hill would be open every day except Monday, but that was the 2025-26 schedule. For now the homepage just says "Closed for the season." Your best sources are nutthillwinterpark.com and the hill's phone line, 920-400-1318.
The hill also rents out its buildings and slope for private events all year, from family reunions to private skiing or tubing parties. That's another way it earns money between seasons.
The rest of October and November around the hill
Squirrel Fest is one of several fall events in Plymouth, and the dates fall into an easy pattern.
- Friday, October 9, 6 to 9 p.m. Plymouth Arts Center hosts a free reception and silent auction for Paint the Towns in Fall Color, with Max Becker performing, at 520 E. Mill Street.
- Saturday, October 17, 7 p.m. An hour after Squirrel Fest ends, the Rat River Boys play A Tribute to 100 Years of the Opry at the Arts Center. Tickets are $17 in advance and $20 at the door.
- Friday, October 30, 5 to 7 p.m. The Plymouth Chamber's free, all-ages Pumpkin Walk runs along the Riverwalk behind Stayer Park, 39 S. Stafford Street.
- Friday, November 27, 7 p.m. The Holiday Gathering Christmas Parade goes through downtown, followed by a tree lighting at E. Mill, Eastern Avenue and North Street.
October 17 works as a full day. Spend the afternoon on the slope with the acorn hunt and pumpkin roll, then head across town for the 7 p.m. show at the Arts Center. The parade on November 27 lands close to when Nutt Hill opened last year, which was December 16.
If you're planning to buy a season pass anyway, buying it before the snow means you've paid for your winter. It also gives Cheese Capital Winter Park money while it's still getting the hill ready. The $35 pairing ticket helps the same way, and so does a plate of pulled pork bought on the hill October 17.
If you live near West Main Street and want to know how winter-season demand affects what your home is worth, Craig Kasten can walk you through it with a free home valuation and consultation, whenever you're ready, even before the first snow.
