Milwaukee is hosting the Republican National Convention July 15 - 18, 2024. Discover where to stay, meet, dine, and unwind here in Wauwatosa - right in Milwaukee’s backyard. Learn More


Hike, Eat and Tour Your Way Through Tosa Outdoors This Winter

Night sky in wauwatosa

If you think you’ve missed the window for the best time to visit Wauwatosa during our warm-weather months, you’re in luck because our cold-weather activities are truly some of our most magical. With countless open-air parks and trails to explore, numerous local restaurants with heated outdoor dining, and historic architecture to tour, there are so many ways to get the full Tosa experience, safely, when you visit during the fall and winter months

If you’re like us, you’re not quite ready to pack up and head indoors for the season, which is why we’ve put together some of our favorite things to do and see outdoors in Wauwatosa this winter. 

Take A Hike

We’re always looking for any excuse to get outdoors—especially, on one of Tosa’s warmer winter days. With so many open-air parks in Wauwatosa, the hardest decision is not choosing between going for a run, bike ride or rollerblading, it’s which stunning park or trail to check out first!

Hart Park. This 19.5-acre park along the Menomonee River has everything you need to get active or just have fun outdoors. During the winter months, enjoy Hart Park’s playgrounds, athletic fields, and eight-lane running track. 

Oak Leaf Trail. Not only is Oak Leaf Trail the perfect secluded space to take in nature’s beauty, but it’s also perfect for cycling, rollerblading, walking, bird-watching or running on its paved 108-mile multi-use recreational trail that encircles Milwaukee County. This trail is also a must for stopping to check out Tosa’s gorgeous foliage throughout the fall.

Hartung Park. Head over to Hartung Park to enjoy walking trails, a playground with swings and bongos, and outdoor fitness equipment. Be sure to stop by the intricate stone labyrinth to take your outdoor adventure to the next level.  

County Grounds Park. Home to various wildlife species including birds, monarchs, butterflies, and more, County Grounds Park is one of the largest remaining open spaces in Milwaukee County. The park consists of the County Grounds Park Loop that’s perfect for hiking, walking, and taking nature trips.

Menomonee River Parkway. If you’re ready to take full advantage of a warm winter day, head over to the Menomonee River Parkway to explore its multipurpose trails that span the entire length of Wauwatosa from Currie Park all the way to the Village.

Dine Outdoors

As the cooler weather comes in, Wauwatosa’s restaurant scene is getting creative. You can now dig into unique outdoor dining offerings at multiple restaurants throughout Tosa’s five dynamic districts.

Cafe Hollander. Located in Tosa Village, Cafe Hollander’s après ski lodge is the perfect spot to warm up with local favorites like house-made cheese curds, the Sconnie burger or tap beer.

Buckatabon Tavern & Supper Club. Buckatabon’s Northwoods Shanties are a must with their heated, private shanties that can seat up to eight people. Enjoy your own space and dig into their Supper Club Nachos, full pound of Buckatabon curds, and Friday Fish Fry.

Eldr + Rime.  Located in the Renaissance Milwaukee West Hotel, Eldr + Rime takes the outdoor dining experience to the next level with their Stugas. Enjoy the New American, Scandanavian-inspired fare from within an igloo all winter long. Reservations are required.

Take A Tour

Become your own personal Tosa tour guide with Wauwatosa Historical Society’s Walking Tour Series, which includes your own personal map and everything you need to know about the unique historic architecture. Here’s a glimpse of some of the hidden gems you may find:  

Little Red Store. Designated as a Wauwatosa landmark in 1978, The Little Red Store stands alone as the oldest remaining commercial building in the city. This adorable red house was one of the only buildings to survive the 1895 fire that destroyed most of the buildings north of the river in Tosa Village.

Old Pabst Tavern. Constructed in1899, Old Pabst Tavern was built with Cream City brick and pointed arch windows and tower to reflect Gothic Revival style buildings. It is now home to Ristorante Bartolotta, which opened in 1993.

The Jacobus Building. Originally built to accommodate the Wauwatosa Fuel and Supply Company that provided fuel oil and furnaces, The Jacobus Building was built by the Jacobus Family in 1924. 

Learn more about where to stay, where to eat, and things to do while you’re here in Wauwatosa. Want a personal itinerary? We’ve got those too! 

Header photo courtesy of @kindof_fit_girl