Falling for Middleton, WI

This Middleton Itinerary at a Glance

Residing minutes from Madison, Middleton offers the perfect blend of outdoor adventure, local flavor and small-town charm for a three-day escape. From cider doughnuts and colorful hikes through Pheasant Branch Conservancy to boutique shopping, cozy coffee shops and a quirky museum dedicated entirely to mustard, every stop adds a dash of delight.

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Check out these great attractions

Clasen’s European Bakery
Pheasant Branch Conservancy
Hidden Cave Cidery
National Mustard Museum

Day-to-Day Middleton, Wisconsin Group Itinerary

Day 1 of Things To Do in Middleton, WI

Falling for Middleton is as easy as dunking an apple cider donut into a caramel latte (don’t knock it until you try it).

That crisp autumn air begs for a warm cup of coffee, preferably paired with one of those apple cider donuts or a morning bun from Clasen’s European Bakery (think sugary cinnamon roll made from pastry), or perhaps a savory croissant from Grace Coffee Co., or a vegan doughnut from Wally Street Co-op.

Then it’s time to set off for your first adventure—a walk, hike or bike ride through Pheasant Branch Conservancy, featuring 682 acres of protected prairie land, creeks, woods and marsh.

Sandhill Cranes nest here in the spring and stay until their young are old enough to migrate in the fall. Middleton’s conservancy and various pond areas see blue-winged teals, great blue herons, wood ducks, green herons, Canadian geese, cattle egrets, double-crested cormorants, bald eagles, pelicans and more.

Lunch options near the conservancy vary from Wisconsin fare at Craftsman Table & Tap, where you can get a cocktail, fried cheese curds, Bavarian pretzels, burgers, fish fry and dessert. Speaking of dessert, next door is Miggy’s Bakes, a locally run bakery with delectable cookies, brownies, ice cream sundaes and cakes. On the same block is Pasqual’s Cantina, a place so famous for its chips that they sell them in grocery stores. Across the street is Lupe’s Taqueria, a small Mexican restaurant with huge flavor and a nice outdoor patio. And just down the street is Chocolate Shoppe Ice Cream Shop, locally owned and bursting with amazing flavors.

Spend the morning or day exploring 30 miles of trails throughout the city, discovering ponds, and taking in the outdoors.

Along one trail is Hidden Cave Cidery, a hard cider distillery that only uses Wisconsin-grown apples to make every batch. It is open Fridays and Saturdays (or by appointment) and has a nice indoor and outdoor seating area.

If you’re still looking for an outdoor excursion after taking in the fall color, check out these area pumpkin patches: Heise Pumpkin Patch, Appleberry Farm, and Kalscheuer’s Pumpkin Patch (where kittens, goats and piggies keep you company while shopping), and Enchanted Valley, which also has a corn maze for all ages.

End the evening around a fire pit at Longtable Beer Cafe, downtown, and choose from their stock of 300-plus types of beer and seltzers and enjoy a menu that always reflects what is in season. Another downtown dining spot includes Villa Dolce, located in a historic building. The family has been serving delicious Italian dishes for nearly 20 years. Middleton also has 12 restaurants with Friday fish fry on the menu, year-round.

DAY 2 of Middleton, Wisconsin Attractions

Begin the day with the full diner experience at Hubbard Avenue Diner, downtown, or Prairie Café, on the north side. Both diners do not disappoint and offer a variety of breakfast platters, specialty items, a full bakery counter and coffee and teas.

Then, walk it all off while checking out the shops downtown. Journeyman Co. is a men’s clothing and gift shop and just next door is Cloth & Metal, a women’s store that specializes in sustainable and environmentally friendly products; and she is a certified welder who makes beautiful, delicate jewelry.

Pick up something special for those at home from Little Pop Color Shop and Regal Find.

And around the corner is the famous National Mustard Museum–home to more than 6,500 mustards with a quirky gift shop above and a free museum below. The National Mustard Museum brings in thousands every year to check out the mustards for sale, as well as other Wisconsin favorites like honey, barbecue sauce, maple syrup, and more. They also sell cheeky gifts, kitchen gadgets, and merchandise. The museum’s curator provides group tours with advance notice, and the Tasting Bar allows folks to sample before buying. If traveling a bit earlier, mark your calendars for the annual National Mustard Day festival, always the first Saturday of August.

There are 12 downtown restaurants to choose from for lunch, including Sofra Family Bistro, an Albanian-American restaurant with a secret recipe for sausage. Down the street is Free House Pub, with a lovely courtyard for seating and several indoor bar areas–try the parmesan fries.

There are far too many local favorites, but Takara 88 for sushi, and Taza for Mediterranean are also never-fail options.

Then, head over to Greenway Station to finish the shopping day out at a 46-acre open-air shopping area, right next to four Middleton hotels and multiple great options for dinner. Try Cooper’s Hawk Winery and Restaurant for beautiful steak medallions with Mary’s potatoes and top it off with a glass of Barrel Reserve. Biaggi’s Risortante and Johnny’ Italian Steakhouse are also fantastic choices in Greenway Station, both with very different vibes but have delicious menus.

Day 3 of Middleton, WI Activities

After a day outdoors and more shopping, switch things up with other Middleton options like X-Golf, to Pleasant View Golf Course, and Marshall Boats (Memorial Weekend to Labor Day), Kickstarter Bar (arcade bar), and more.

Or consider Middleton the perfect home base. The city is perfectly situated within an hour of multiple area attractions like Cave of Mounds, Taliesin, House on the Rock, World’s Circus Museum, International Crane Foundation, Sassy Cow Creamery, New Glarus, Mount Horeb, and so much more. Not including all there is to do in Madison.

Stay at one of Middleton’s nine hotels, pick a direction and make a day out of it, returning back for another amazing dinner at one of the city’s 80 restaurants and diners. Consider an evening glass of wine at Grape Water Wine Bar, or a beer at MidTown Pub, or a cocktail at 1847 at the Stamm House–the longest running establishment in Middleton: it began as a tavern in 1847 and still serves as a modern-day supper club today with a gorgeous outdoor patio.

Catch live music at Capital Brewery’s bier garten–open until the snow falls. Capital Brewery is a German-style micro craft brewery—the oldest still running in the state. Known as “Middleton’s Backyard,” the bier garten has no dress code and invites patrons to bring their own food.

Stone Horse Green also hosts outdoor entertainment on Thursday evenings until the snow falls. Its schedule of outdoor movies, live bands, and bingo nights are online to choose from