Madison, Wisconsin is only 2.5 hours from Chicagoland. Madison is the Capital of Wisconsin and is home to the World’s Largest Brat Fest. 

National Geographic rated Madison one of the Top 10 happiest cities in the world, and with 5 sparkling lakes and the University of Wisconsin at Madison, this city consistently rates high among the top places to live.

Madison, Wisconsin: Group Family Trip
Madison, Wisconsin: Group Family Trip

Depending on what time of year you decide to go there are some really fun festivals such as  – The Taste Of Madison, Yum Yum Fest, Isthmus Food Cart Fest, and Restaurant Week.

Where to Stay

Hotel Red

HotelRED is a dog-friendly, boutique hotel that has 48 rooms in the entire hotel. HotelRED is located across the street from the University of Wisconsin-Madison and conveniently located 2 miles from the Madison Museum of Contemporary Art & 7 miles from Dane County Regional Airport.

Lobby of HotelRed | Madison, Wisconsin | Pet & Kid Friendly Hotel
Lobby of HotelRED | Madison, Wisconsin

Since we were planning this weekend trip with another family of three plus their au-pair, we wanted to find lodging that could accommodate both our families and their dog Shelby. HotelRED was an ideal choice because they are the only hotel I could find in the area with two bedroom suites and that is dog-friendly!

HotelRed Dog Friendly Madison WI
2/2 Bedroom Suite | HotelRED | Madison WI

This hip and modern hotel has trendy furniture, fully equipped kitchens as well as 1 or 2 bedrooms suites. Private patios have lavish seating. All of their hotel rooms have free Wi-Fi. The studios have flat-screen TVs and kitchenettes. Their 1- and 2-bedroom suites have large, modern tubs, furnished balconies, sofa-beds and/or separate living rooms.

The Wise Restaurant inside HotelRed | Madison, Wisconsin | Pet & Kid Friendly Hotel
The Wise Restaurant inside HotelRED | Madison, Wisconsin

The Wise Restaurant and Bar is their on-site restaurant and can be booked via Open Table. This young and fun restaurant has Drag Queen Bingo and Happy Hour Menus. These are just some of the unique features that are all part of the HotelRED experiential stay.

Olivia & Juju trying to pose with Shelby | Dog Friendly HotelRed | Madison, Wisconsin
Olivia & Juju trying to pose with Shelby | Dog Friendly HotelRED | Madison, Wisconsin

Parking is included in your room rate, as well as local/airport shuttle service, and seasonal use of bikes, kayaks, paddleboats and paddleboards. There’s also a 24/7 gym and an onsite restaurant and bar. 

Shelby enjoying the treats at check-in | Dog Friendly HotelRed | Madison, Wisconsin
Shelby enjoying the treats at check-in | Dog Friendly HotelRED | Madison, Wisconsin

Shopping

Shopping on State Street is the prime spot. Easily the most iconic area of Madison, State Street is a long street that leads from the UW campus to the Capitol. It’s lined with bars, restaurants and hippie shops and is oh-so very fun. You can get lost for the whole day here.

I can’t wait to check out Capital Kids, and Little Luxuries. To buy Wisconsin shaped cutting boards: Orange Tree Imports, and for fair trade items: Servv.  

Because my family and I are cheese-oholics we are definitely making a stop into Fromagination  where you can taste and smell the cheeses before making your selection. Fromagination is located on Capital Square in Madison.

And we plan on bringing back treats from Candinas Chocolatiers for Mimi and Papa.

Dog Friendly Madison

Our friends dog Shelby is tagging along with us on this trip. Sycamore Park is an off-the-leash dog park that also has a playground for the girls.

The Graduate Madison  hotel is also dog-friendly and Camp Trippalindee (their rooftop restaurant)  is dog friendly with s’mores kits and root beer floats for the kids (and adults).

The Rooftop of The Graduate | Madison, Wisconsin
The Rooftop of The Graduate | Madison, Wisconsin

Where to Eat

Merchant has a Saturday Farmer’s Market Brunch from 9am-3pm. And since we are big fans of really cool meat boards, this place is a must try.

With restaurants like: GraftHeritage TavernGraze, and Pig in a Fur Coat,  I think the Chicago foodies on this trip will be good to go!

Things to Do

The State Capitol building is gorgeous and totally requires a selfie with your kids.

Rent bikes at Budget Bicycle Center. They have a huge selection of kids bikes and the trailers that attach behind bikes for the kids and dogs to ride in.

Olbrich Botanical Gardens has a Thai Pavilion, Conservatory, Rose Garden and more. The Gardens are free with donations appreciated and the Conservatory is $2 for adults and free for children. (FREE)

Rent bikes at The UW Arboretum  where the kids can ride behind your bike. The Arboretum has three garden collections where you can run, walk, photograph and enjoy nature.

Have beers at the UW Madison Memorial Union Terrace. It’s a huge terrace by the lake with great sunset views, cheese curds and plenty of beer options.

Henry Villas Zoo is one of the only free zoos in America and has some great exhibits. We had a blast here feeding the goats, riding the merry-go-round and playing at their playground. We would have stopped over to the beach at Lake Wingra afterwards but the rain moved in. (FREE)

Henry Vilas Zoo | Madison, Wisconsin
Henry Vilas Zoo | Madison, Wisconsin
Henry Vilas Zoo | Madison, Wisconsin
Henry Vilas Zoo | Madison, Wisconsin
Henry Vilas Zoo | Madison Wisconsin
Henry Vilas Zoo | Madison Wisconsin

Lake Wingra is great for kayaking or paddling boarding. On one far corner you can even see the Capitol. During the winter you can go ice skating here. Here is a bike trail map.

Governor Dodge State Park is about an hour and a half drive from Madison. This park since it has two lakes, and one of them you can swim across the lake to a secluded hiking spot. It also has horseback riding trails, camping sites and lots of hiking trails.

Unique Things To Do

Madison is home to the National Mustard Museum.  About a 15 minute drive from downtown Madison, it’s home to more than 6,090 mustards from all 50 states and more than 70 countries , the Mustard Museum has been featured on Oprah, Jeopardy and To Tell the Truth. Best yet, it’s FREE! Started by Barry Levensen, who left his job as Assistant Attorney General for the State of Wisconsin to open what is now one of Wisconsin’s most popular attractions. (FREE)

Kids posing at the Mustard Museum | Madison, Wisconsin
Juju and Olivia posing at the Mustard Museum
Our Kids and Munchkins | Mustard Museum | Madison, Wisconsin
Our Munchkins | Mustard Museum | Madison, Wisconsin
Mustard Museum Wall Art | Madison, Wisconsin
Mustard Museum Wall Art | Madison, Wisconsin

If you don’t mind driving about an hour west of Madison, House on the Rock is a quirky architectural attraction featuring a rambling, Japanese-style home on a 60-ft. rock face. Many describe this house as bizarre, eerie, and fascinating. Located in Spring Green, Wisconsin, this house  has admission from $15 to $30, depending on how much of the House you want to see.  House on the Rock was the crazy vision of Alex Jordan Jr., a recluse who turned his home into America’s largest, strangest indoor sideshow (And later served as a rendezvous point for deities in American Gods. 

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