Things to Do in Waukesha County & Milwaukee County This Weekend ☀️Wisconsin summer weekends do not mess around. The second we get a stretch of warm weather, everyone collectively decides we
Dated: December 26 2025
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Winter in Waukesha County: 2025 Sledding Hill GuideWinter in Waukesha County isn’t just about braving the cold—it’s about finding ways to enjoy it. When the snow piles up, our parks turn into sledding spots where families and kids trade shovels for sleds and cabin fever for downhill fun.
And just like choosing the right home, picking the perfect sledding hill comes down to location, comfort, and the memories you’ll make there. Whether you’re new to the area or simply ready to try a different slope this season, this guide is your go‑to list of sledding hills across Waukesha County.
🌟 Calhoun Park – New Berlin
Best For: Variety for all ages
❄️ Hill: Northwest slope allows sledding and tobogganing; a smaller hill for younger children
🚗 Parking: South entrance
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: 1848 Coffee, Sister’s Brew
🌲 Extras: Baseball fields, fishing areas, picnic shelters
Best For: Local families
❄️ Hill: Solid incline with open sledding space
🚗 Parking: Park lot
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: Stone Creek Coffee, Milwaukee Street Traders
Best For: Kids of different ages
❄️ Hill: Smaller hill for younger kids; steeper areas for older kids
🚗 Parking: Available
🚻 Restrooms: Closed during winter
💲 Cost: Free
☕ Nearby Coffee: Whelan’s Coffee, Roots Coffee Bar, Java Hut, River Coffee
Best For: Younger kids
❄️ Hill: Small, gentle slope
🚗 Parking: Available
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: 1848 Coffee, Sister’s Brew
Best For: Big-hill adventure
❄️ Hill: Large hill; short hike required
🚗 Parking: Available
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
Best For: Family-friendly sledding
❄️ Hill: Suitable for all ages
🚗 Parking: Available
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: Shanahan’s Coffee, Espresso Love Coffee, Brew52
Best For: Free sledding close to town
❄️ Hill: Suitable for all ages; caution during icy conditions
🚗 Parking: Street parking near the top or the lot at the bottom of the hill
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: Brewers Two Café, Good Eats Café
🌲 Extras: Playground, tennis courts, baseball fields, basketball courts
Best For: Families of all ages
❄️ Hill: Wide, well-maintained hill
🚗 Parking: Available
🚻 Restrooms: Seasonal facilities
💲 Cost: Free
☕ Nearby Coffee: Loca Latte, Starbucks (Hwy 164)
Best For: Spacious, safer runs
❄️ Hill: Approximately 250-foot run with long run-out
🚗 Parking: Archery Lot
🚻 Restrooms: Heated flush toilets at beach house; pit toilets near SCUBA lot
💲 Cost: County park fee required
☕ Nearby Coffee: Quarry Coffee (Lannon), Loca Latte (Sussex), Kwik Trip
🌲 Extras: Cross-country skiing, snowshoeing, archery, horseback riding
Best For: Wide hills for all ages
❄️ Hill: Large open sledding area
🚗 Parking: Picnic Area #4; overflow at #5
🚻 Restrooms: Heated flush toilets at Picnic Area #5
💲 Cost: County park fee required
☕ Nearby Coffee: Mama D’s, Le Café Bistro
🌲 Extras: Hiking, snowshoeing, ice fishing
Best For: All-ages sledding with room to spread out
❄️ Hill: Open hill near dog park
🚗 Parking: Near dog run
🚻 Restrooms: Porta-potties available
💲 Cost: Free
☕ Nearby Coffee: Goddess and the Baker
🌲 Extras: Trails, picnic areas, river views
Best For: Older kids and teens
❄️ Hill: Steep, popular hill; solid workout
🚗 Parking: East end of Picnic Area #4
🚻 Restrooms: Flush toilets at Picnic Areas #2 and #3
💲 Cost: County park fee required
☕ Nearby Coffee: Shanahan’s Coffee, Espresso Love Coffee, Brew52
Best For: Younger kids
❄️ Hill: Gentle slope
🚗 Parking: Picnic Area #2
🚻 Restrooms: Flush toilets
💲 Cost: County park fee required
☕ Nearby Coffee: Inclusion Coffee, Birch & Banyan, Creole Café
🌲 Extras: Ski and hiking trails
Best For: Older kids who don’t mind a hike
❄️ Hill: Large hill; walk-in access
🚗 Parking: Small lot
🚻 Restrooms: None
💲 Cost: Free
☕ Nearby Coffee: Whelan’s Coffee, Roots Coffee Bar, Java Hut, River Coffee
Best For: All-day sledding
❄️ Hill: 50-foot hill; open 9 AM–10 PM
🚗 Parking: Available
🚻 Restrooms: Heated winter restrooms
💲 Cost: Free
☕ Nearby Coffee: The Gingerbread House, Vintage Grounds
🌲 Extras: Outdoor ice rink
Best For: Younger children
❄️ Hill: Gentle slopes
🚗 Parking: Off-street parking
🚻 Restrooms: Seasonal portable toilet
💲 Cost: Free
☕ Nearby Coffee: The Gingerbread House, Vintage Grounds
🌲 Extras: Playground, walking trails, shelter, picnic tables, open turf area
Best For: Small children
❄️ Hill: Gentle slopes
🚗 Parking: Street parking only
🚻 Restrooms: None
💲 Cost: Free
Best For: Local families
❄️ Hill: Popular neighborhood hill
🚗 Parking: Park lot
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: Loca Latte, Quarry Coffee
Best For: Evening sledding
❄️ Hill: Lighted sledding hill
🚗 Parking: Available
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: 1848 Coffee, Sister’s Brew
Best For: Family-friendly sledding
❄️ Hill: Suitable for all ages
🚗 Parking: Available
🚻 Restrooms: Not confirmed in winter
💲 Cost: Free
☕ Nearby Coffee: Sister’s Brew
Best For: Wide, open sledding
❄️ Hill: Spacious and open
🚗 Parking: Park in the lot or behind the fire station
🚻 Restrooms: Seasonal portable restroom
💲 Cost: Free
☕ Nearby Coffee: Mama D’s, Buzz Café, Black Canyon Coffee
🌲 Extras: Disc golf, playgrounds, sports fields
Families bundle up for sledding, skating, and snowy adventures, then head back to neighborhoods that feel like home year‑round.
The Hupke Team at RE/MAX Forward is proud to be part of that story. In 2024, we helped 121 families close on homes, totaling over $38 million in sales, and earned 130+ five‑star Google reviews. Because we don’t just sell houses—we live here, raise families here, and know these communities season by season. 🏡❄️

⚠️ Before You Go
Snow days can be unpredictable! ❄️ Restrooms, parking, and hill conditions change with the weather, so think of this guide as a starting point, not a guarantee. 🚗🚻
👉 Quick tips:
Check posted signs before you sled 🪧
Keep an eye on the kids 👀
Ride safely and responsibly 🛷
That way, the only surprise you’ll get is how much fun you have flying down the hill. 🎉
Jennifer has been a trusted name in Southeastern Wisconsin real estate since 2003. With over two decades of experience, she brings a strategic, detail oriented approach to every transaction, whether i....
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