Bordering Madison’s west side, Middleton is known as “the good neighbor city”.  It is one of the fastest-growing areas in Wisconsin, yet it maintains a small-town feel. Locals are always working towards building a community. It ranked #1 on CNN’s Best Places to Live.  In Middleton, you’ll find friendly neighbors, ponds, trails, parks, a bustling downtown. Middleton is a fantastic neighborhood to invest your heart in.  

History of Middleton

Like many American lands, the history of Middleton begins with Native American habitation. Its many waterways and lakefront real estate made it an ideal campground for natives. The area was inhabited first by the Algonquin tribe and then by the Ho-Chunk tribe. The site is famous for the ritualistic burial mounds formed by the Algonquin. After European settlement, a fur trading post was established here.

A railroad stop was built in the area. This was responsible for the spark that transformed Middleton into how we know it today. The train stop was known as “Middleton Station”… but we’ve since dropped the “Station”.

For decades, Middleton was an agricultural hub. Wheat was its big cash crop.  But as the area expanded throughout the 1800s, several other trades were established. There was a stone quarry, a lumberyard, a tin shop, a pickle factory (yum!), a blacksmith, and an opera house.

A wheat disease spread rampantly throughout the late 1800s. This inspired Middleton residents to switch their focus from wheat to dairy and helped to establish America’s Dairyland we all know and love today.

Many of the early European settlers in the area were German. For many years, Middleton was known almost as a “little Germany.” The newspaper even printed two separate publications… one written in English. And another in German. If you’re a history buff, you may even be able to track down some copies of this at the Middleton Library.

Recreation in Middleton

Striker’s Pond

Striker’s Pond was created from a glacial event over 10,000 years ago. It has since become a lush wetland prime for spotting wildlife. It’s not uncommon to see turtles, frogs, and various wading birds like Heron, Cranes, and Warblers. Walking, biking and bird-watching trails scatter the area.

Pleasant View Golf Course

A pleasant view is more than just a golf course. While it does have a highly-rated 18-course game, it also has a great bar and grill, ski, and bike trails. It’s also won the “Best of Madison” award three years in a row. Whether you’re a golfer or not, it’s worth checking out!

Lakeview Hill Park

This park claims the highest point in Madison. This 27-acre conservation park offers the best views of Lake Mendota in the City. Picnic tables and trails are plentiful. 

Pheasant Hills Conservancy

Pheasant Hills Conservancy is a steward of the land. The 550-acre natural area hosts wetlands, grassy plains, and forested hills. Over 2.6 million gallons of freshwater flow from the natural springs in this park. Check out the trail map here.

Middleton Hills Park

This neighborhood park features a boardwalk trail over lush wetlands. There are lots of activities for children and families including two playground equipment areas, a sand volleyball court, basketball court, and soccer field.

Middleton Community 


The Cross Plains Area School District has an impressive 96% graduation rate. The High School was ranked the #2 best High School in Madison. Read more stats about local Middleton schools here.

Downtown Middleton 

Downtown Middleton is bright, busy, and a lovely place to spend the afternoon. It’s highly walkable with lots of boutiques and attractions. The city provides a free trolley service that can transport you around the bustling entertainment district. 

If you’re new in town and like to stay active, the Capital Brewery Bike Club is a great way to meet new people. The club has been going strong for 12 years. Over 100 riders meet for a group ride every Tuesday and Thursday (weather permitting!) and conclude the ride by enjoying a beer in the brewery’s famous beer garden. 

Annual Events

The Wine Walk

This one happens every spring in Middleton, usually in May. It’s a great way to expand your pallet while supporting local businesses. Participants walk to each sponsored business, sampling different wines in each location. Friends are made. Pallets are expanded. And all proceeds benefit Domestic Abuse Intervention Services.

National Mustard Day

Hosted by the local Mustard Museum, you can celebrate (arguably, the best) condiment on the first Saturday of every August. There is a full weekend of street festival events. You’ll also experience live music, games, and free mustard tastings. You may even get to waltz with the Duchess of Mustard.

Haunted Hustle Races

To celebrate Halloween, Middleton hosts a spooky-themed race and Zombie-walk. Bonfires, s’mores, and entertainment are available after you’ve finished running for your life.

Good Neighbor Festival in August

Good Neighbor Festival 

A fun neighborhood festival with carnival games, entertainment, crafts, and more. Held in Fireman’s park every August.

Best Places to Dine and Drink in Middleton

Greenway Station 

Greenway Station is a beautifully landscaped, open-air mall in Middleton. Restaurants and shops abound. You can easily spend all day walking around, dining, and drinking in Greenway Station. View a complete list of restaurants here. 

Villa Doce 

Home-made gelato, fresh pizza, and lite bites. A charming atmosphere on the main drag of Madison, Villa Doce is a local favorite. 

Craftsman Table & Tap 

Classic American fare, done right. The polished atmosphere is for a girl’s night or watching the game. 

Longtable Beer Cafe

A unique bottle-shop cafe concept with communal seating designed to help you meet new neighbors. Their namesake community table seats 22 comfortably. They have over 300 beer options in their grab-and-go cooler, firepits, and gorgeous charcuterie boards. 


An intimate dining experience that portals you to the New Orleans French Quarter. Their menu is a creative twist on classic Bayu meals. You’ll get to try menu items like crawfish cheesecake, pulled pork crepes, and etouffee. Your meal will be accompanied by live jazz and blues piano. 

Vin Santo 

A neighborhood gem with a robust wine list and a well-balanced Italian menu. This menu is one best enjoyed in courses…because each course is better than the last. 

The Village Green

Where the locals hang out. This tavern is your classic casual home-town tavern. Comfort food takes the form of a perfect burger and fries.

Capital Brewery

Capital Brewery has graced Middleton with award-winning craft brews for almost 30 years. Known as “Middleton’s backyard”, its bier garden hosts live music every weekend from May-September. These events are widely popular, and it’s not uncommon for over 1,500 music lovers to pour into the garden during the summer. 

Homes for Sale in Middleton

Middleton neighborhoods are all fantastic. The price median is set at $426,419. But the overall price of a Middleton home varies quite a bit, as does the architectural style. No matter what your preference is, there is something for everyone in Middleton. Check out current Middleton listings here.