Madison, Wisconsin is home to us – we both grew up near here and chose to raise our families here. The summers can’t be beat – such a variety of good outdoor spaces and activities, local events, and dining options. Things get a bit trickier in winter but over the years, we’re learning to embrace the seasons and survive winter!
Even if you’re not located in the Madison area, hopefully these tips and ideas can help make the most of the seasons wherever you live! (Unless of course you live somewhere sunny and warm year-round. Then invite us to come join you for a visit! 🙂
1. Get outside
It’s way too easy to look out the window or look at the thermometer and make the decision to stay in. We’re certainly not going to venture out much when it’s below zero, but we’ve been fortunate to have a mild winter in Wisconsin so far. With the right outdoor apparel, its not so bad. So throw on those long underwear and get outside! Build a snowman. Make a snow fort. Have a snowball fight. Take the dog for a walk. Find a sledding hill. If it’s a mild day, go hiking. Just get outside! We almost never regret getting out.
2. Ice Skating
Tenney Park Outdoor Rink – located on the edge of Lake Mendota, this is a very large open outdoor and naturally-occurring rink (weather dependent of course). There is a nice warming house with concessions, fireplace, and skate rental for the whole family. Outdoor stadium lights provide lighting for skating after dark. Ample free parking lot and street parking available. Visit their website for more information and special events.
Ice Rink at the Edgewater – another (man-made) outdoor rink in downtown Madison. Located on the property of the Edgewater hotel, there is a variety of dining and drink options. Skates available to rent here as well. A parking ramp across the street can be somewhat limited. The patio overlooks Lake Mendota and has outdoor fireplaces to warm up by, plus the whole area is beautifully lit and decorated at night! Check out their website for more info.
(Tip: if you’re looking to eat elsewhere, Camp Trippalindee is near the parking ramp and was a unique and fun dining experience!)
Local outdoor rinks – most communities have some outdoor rinks, so worth looking into. Not all have skate rental available on-site, but visit Sun City Cyclery and Skates in Sun Prairie, Wisconsin. They have seasonal skate rentals for a decent price if you plan to go multiple times.
3. Visit a ski hill and learn to ski
If you live in in the Madison area there are few great options for skiing nearby. We took our six year old a couple times this year and it was a huge hit. We lucked out with good weather both days but they were days to remember and our daughter had a blast trying something new. The first time we went, we signed our daughter up for a ski lesson at Cascade. Read this post for more info!
We also went to Devil’s Head during learn to ski week. Our daughter did a 1.5 hr lesson that day. It was also a great experience. By the end of the day she was able to go down runs without falling. I think the views at Devil’s Head are prettier but some say the snow at Cascade is better. I also liked the “magic carpet” at Devils Head better, it seemed less busy. There are pros and cons to both locations but either are a great option!
A few of the ski hills also offer snow tubing for those who aren’t interested in skiing or snowboarding. We’ve only been to the snow tubing at Cascade Mountain and everyone enjoyed it!
4. Visit a New City / Town
While there are plenty of local options, it’s fun to explore new cities and towns year-round. Most people flock to northern Wisconsin to enjoy the winter activities – skiing, snowmobile, ice fishing, etc! We took a fall trip together with our families to Boulder Junction, Wisconsin and stayed in the cutest, coziest cabin! See our post on this trip here if you’re looking for a fun weekend getaway.
Every winter for the past 10 years, Katie’s extended family takes a long weekend trip to northern Wisconsin. This year, they stayed in Eagle River, WI and rented a cabin on the lake. There were four families and 7 kids between them, so all the cousins had a blast playing together. Everyone had something to entertain themselves – ice fishing, snowmobiling, playing on the playset in the snow, and spending time together. A full blog post will be coming soon with all the details!
Our friends in Chicago invited us down to spend the weekend with them in the Windy City. We went without kids for this trip, so we had fun eating and drinking our way around the city! A nice change of pace and was so good catching up with friends we haven’t seen in a while.
We’ve also taken trips to Chicago around the Christmas holiday – hotels in the city can actually be pretty cheap (usually less than $100 if you look) and the city is decorated so pretty for the holidays.
Even if it’s just a day trip – look at some of the local events and happenings and pick a destination! Go to Pewaukee, WI for a shopping day or plan a girl’s night out and visit some wineries! Click the links for some of our suggestions.
Balanced Rock Winery 
Shopping in Pewaukee, WI
5. Plan a warm weather trip
One of our favorite ways to survive winter, for sure. 🙂 We started planning our Spring Break 2020 trip after we took separate family trips in 2019. Sara returned home from Florida (see this post for all the details!) and Katie from Arizona, and we both agreed it was so nice having a warm weather vacation to look forward to.
Sedona, Arizona 
Fort Myers Beach, Florida
After a lot of researching and planning (our specialty), we landed on a small island on the Gulf Coast of Florida called Anna Maria Island. After more researching and scouring vacation rental sites, we found the perfect little house for the 8 of us. We’ve kept ourselves busy this winter searching for low cost van rentals, plane tickets, and other vacation logistics like shopping online for beach clothes and reading the travel forums on TripAdvisor to get some activity and dining ideas.
6. Check out Local Events
There’s usually quite a bit happening on the weekends in the area. When we’ve got nothing planned, we’ll usually go on the “events” tab of Facebook and scroll through the local happenings. This is how we’ve found a lot of the activities we’ve done this winter, like Movie in the Park at Tenney Park outdoor ice rink (see # 2), Learn to Ski Week (#3) and Family Fun Night at Prairie Athletic Club (#7).
Around the holidays (and even after), the Henry Vilas Zoo is a fun place to visit. We took the kids to the Zoo Lights event before Christmas to look at the Christmas lights but the favorite activity was the carousel.
7. Indoor Activities to Burn Energy
When the weather doesn’t lend itself to getting outdoors (remember the Polar Vortex of 2019 when we had wind chills of -50 degrees?!), the surrounding Madison area has plenty of indoor options too. A few of our favorite places to visit when it’s cold outside and need to burn some energy include:
Play N Wisconsin, located in Middleton, WI
An indoor open gym with plenty of activities to keep the kids busy. They sell play huge structures that are available to purchase, but someone had the genius idea to have them all set up inside for the kids to play on. There are also trampolines, basketball hoops, and plenty of other little activities. Prices range from $7-9 per child, so this gets a bit pricey but is a good activity for those really bad winter days.
(Tip: when you’re done playing, grab cheap and delicious cheeseburgers at The Village Green in Middleton).
Prairie Athletic Club, located in Sun Prairie, WI
This is a huge indoor gym and sports complex that requires a membership to use. However, they have Family Fun Nights on Saturday evenings during the winter months that are available to non-members. Visit the website for the list of dates, activities, hours, and cost. (*Note: I had called in advance the night we went, and was told it started at 4pm despite the website listing 5:30pm so worth checking into).
It was a great way to spend a snowy night – the featured activity when we went was an indoor Bounce House, plus we played basketball, soccer, and finished our night at the indoor pools. The restaurant has food and beverage specials during this time as well. Kids had a blast and slept really well that night!
(Tip: get dinner before at Buck and Honey’s restaurant down the street. You can make online reservations, the food is amazing and then you can burn off all the calories from the delicious meatloaf later at the PAC).
Open Gym at local Gymnastic clubs
Most gymnastics clubs and even some karate gyms feature some Open Gym time. This is another one of our go-to activities when we have to burn some energy indoors. Some of the places we’ve been to over the years include:
- Jump Around in DeForest, WI
- Badger Gymnastics in Waunakee, WI and west Madison, WI
- Go Ninja in Waunakee, WI
- Prairie Kids Club in Sun Prairie, WI
- Madtown Twisters both east and west Madison, WI
- Plus many of the indoor trampoline and activity parks in the area
8. Restaurant Options Indoors
Another favorite winter activity in Wisconsin is eating and drinking (hehe). While the list is endless, here’s a few of the more unique food experiences we’ve done this winter:
Garver Feed Mill – northeast Madison, WI
- Huge indoor space with something for everyone!
- Late Winter Farmer’s Market – see website for hours
- Food options include:
- Ian’s Pizza (and salad/wrap bar), Surya Cafe, Calliope Ice Cream, Ledger Coffee Roasters, and more
Ledger Coffee Roasters 
Ian’s Pizza 
Farmers Market 
Such an awesome space to visit for the Winter Farmers Market
Camp Trippalindee – downtown Madison, WI
Traditional Supper Clubs like Cimaroli’s in Portage, WI
Nearly every small town in Wisconsin has an old-school supper club for a Friday Fish Fry. Just ask the locals! (Then plan to hit the gym Saturday morning!)
9. Have a winter bonfire
Bundle up and have a bonfire. Just because its winter doesn’t mean you can’t enjoy a fire. We had several this winter on warmer days and they were really enjoyable. Give it a try!
10. Stay In.
Our kids’ favorite activities on a snowy winter night is the simplest and least expensive! Build an “eagle nest” on the floor with pillows and blankets, have hot cocoa, make indoor s’mores, and have a movie night together.
(Looking for a new hobby or need new blankets? Katie’s DIY Tie Blanket Tutorial post will teach you how to make the world’s best blankets to add to your collection for building eagle nests!)
Since we live a few houses away from each other, we often end up at one of our houses if there’s nothing going on. The kids keep themselves (mostly) entertained and we pour a drink, either grab take-out or make some snacks, sit down at the table and have a game night. With early bedtimes for us, of course. 🙂
Settlers of Catan 
Dominoes
Feeling like entertaining? Host a get-together for friends. It doesn’t have to be anything fancy. We’ve had some really fun nights that we put together last minute, like our impromptu Halloween Party, or a planned event like Katie’s Holiday Party.
With all those activities and ideas, we hope it’ll inspire you to get outside! Also, is it spring yet?
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