Things to Do Outside in Milwaukee During the Winter

It’s officially winter, and the coldest days are still ahead. And while many of us are content to stay in the warmth of our homes, snuggled up with a blanket and a good book or movie, others can get a little restless when they’re holed up inside for too long. Thankfully, there are plenty of options for those who don’t mind feeling the chill of winter on their skin. Here are 13 ways you can embrace the cold in Milwaukee this winter. Don’t forget your gloves!

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1. Winter Festivals

The holidays may be over, but that doesn’t mean the celebrating has to end. Winter festivals are typically daylong outdoor events with seasonal food and drinks, music, games and other activities. They’re very family friendly and can be enjoyed with others or all by yourself! There are tons of winterfests happening all across the Milwaukee area this season, and we’ve listed some (but certainly not all) below.

DelaFREEZE: Jan. 13, 10 a.m.-3 p.m. in Downtown Delafield
West Allis Winter Week: Jan. 14-20, Various times and locations in West Allis
Waukesha JanBoree: Jan. 19-28, Various times and locations in Waukesha
Winterfest 2024: Jan. 21, 10 a.m.-2 p.m. at Boerner Botanical Gardens
Ice Bear Fest: Jan. 27, Time TBA at Third Space Brewing
Winter Carnival: Jan. 27, 2-4 p.m. at Elite Clubs Mequon
Mitten Fest: Feb. 3, Noon-8 p.m. at Boone and Crockett
Cedarburg Winter Festival: Feb. 17, 8-9 p.m. and Feb. 18, 8 a.m.-3 p.m. in Downtown Historic Cedarburg

2. Farmers Markets

Most of us associate farmers markets with fresh seasonal produce and warm summer mornings, but there are several that run twelve months a year – the Fondy Market, for example – and a few, such as the Capitol Drive Winter Farmers Market (formerly hosted in the Deer District), that are actually dedicated to winter. You can still purchase fresh food and locally produced art and crafts while enjoying a warm, cozy drink. While most of these events are indoors, you can walk to the closest neighborhood market to get your breath of fresh air.

3. Hiking

Most of Wisconsin’s hiking trails are open year-round, so you can enjoy what nature has to offer no matter the weather. Take a more leisurely stroll on the paved Oak Leaf Trail in Milwaukee, or pull on your boots and double-socks for a more rugged hike on the Ice Age Trail. If you’re looking for something a little more social, consider attending an organized hike, like the Mequon Winter Frolic or the Urban Ecology Center’s Winter Sunrise Hike.

4. Outdoor Dining

Have a bite to eat or a full-on feast at one of Milwaukee’s dozens of outdoor dining options. Many of these venues are heated, but it’s best to bring your coat and hat anyway. Check out At Random’s seasonal “Magic Forest,” including outdoor huts and festive lights, or the Northwoods Shanties at the Buckatabon Tavern and Supper Club in Wauwatosa. Be sure to secure your reservation ahead of time!

5. Ice Skating

Each winter, Red Arrow Park in downtown Milwaukee lays down its “Slice of Ice” for people of all ages and abilities to enjoy. You can rent equipment right on site, and skating is free for those who bring their own skates. The rink is also available for school trips and birthday parties. Or get out in nature, if you have your own skates, and find a frozen pond or river to skate on (just make sure the ice is thick enough; at least four inches is a good rule of thumb). Consider firing up a friendly game of pond hockey!

Red Arrow Park; Photo by Visit Milwaukee

6. Ice Fishing

Nothing screams “up-north winter” like drilling a big hole into a frozen body of water and dropping a line in. Lake Michigan and its tributaries are home to many fish that remain active throughout the cold winters, including bluegill, brown trout and steelhead. You can indulge in the luxury of a heated tent, or rough it with nothing more than a couple folding chairs. If you’ve never ice-fished before, you might try a guided excursion with an expert – many of them take place right on the Milwaukee Harbor.

7. Urban Ecology Center Programs

Milwaukee’s Urban Ecology Center facilitates opportunities for residents to engage with nature every month of the year. During the winter, it hosts group hikes, bird and tree identification sessions, park clean-ups, and more. New activities are being added all the time, so check the event calendar for unique interactions with Milwaukee’s natural urban habitats.

8. Snowshoeing

If you want to explore some of Wisconsin’s more rugged landscapes during the winter, snowshoes are the way to go. They have a large surface area to better distribute your weight, keeping you from sinking into the deep snow, as well as grippy soles to maintain your footing. You can rent snowshoes from the Whitnall Park Warming House in Hales Corners. If you’re crafty, you could even try making your own pair!

9. Snowmobiling

According to the Wisconsin Department of Natural Resources, there are more than 25,000 miles of snowmobile trails in our state, making it a great option for those looking for a fun (and fast!) way to traverse the snowy terrain. Of course, you’ll need the proper safety equipment, and you must obtain a safety certification to ride on public trails.

10. Sledding

Ah, sledding, one of Wisconsin’s great winter pastimes. While we may associate this downhill thrill with childhood, it can be just as fun as an adult. Take a drive to one of Wisconsin’s designated sledding slopes, or wander around your neighborhood until you find that perfect hill. If you don’t have a sled of your own, sporting goods stores carry sleds of all shapes, sizes and functions. You can even use household objects, like storage tub lids and tarps – just make sure you’re well protected before beginning your descent.

11. Skiing and Snowboarding

Wisconsin may not be home to America’s grand mountain ranges, but there are still plenty of options for downhill skiing and snowboarding. Wilmot Mountain is just an hour from downtown Milwaukee, where beginners can take lessons and experienced riders can hop right on the lift. Skis, snowboards, boots and helmets are available to rent on site. If you’d rather stick to level ground, give cross-country skiing a try. There are dozens of trails surrounding Wisconsin’s state parks and forest that can accommodate all skill levels.

12. Fat-tire biking

Fat-tire biking is becoming increasingly popular in regions where snow covers the ground for several months of the year. These bikes have extra-wide tires that enable riders to stay atop snow, much like how snowshoes keep us from sinking as we walk. If you already own a bike, consider putting some winter miles on it by installing wide snow tires.

13. Birdwatching

If you’re looking for something a little more leisurely, grab a pair of binoculars and hit any of Milwaukee’s hiking trails for a birdwatching outing. Many species of birds spend their winters in Wisconsin, and some become easier to spot against the backdrop of the white snow. Additionally, many birds use the coast of Lake Michigan to guide their winter migrations, making Milwaukee and other coastal areas ideal for spotting a variety of birds. To identify the birds, there are several birding apps that list the characteristics of regional species.