Summer Fun Events in Middleton

Now that summer has officially begun, it’s time to fill your schedule with as much fun as possible. From getting up early to play a round at Pleasant View Golf Course or exploring Middleton’s 549-acre protected natural area, to cooling off in the water of Lake Mendota, to ending the day on an outdoor patio with friends, there are so many opportunities in Middleton to fully embrace summer.

Here are just some of the events happening in Middleton this summer (2023). Check out our calendar of events page for more.

Reoccurring/On-Going Events

Greenway Station Farmers Market, 8 a.m. to 1 p.m., every Thursday, now through Oct. 5

Get your share of farm-fresh produce and local goodies at Middleton’s Greenway Station Farmers Market from 8 a.m. to 1 p.m. every Thursday. From in-season produce, beautiful flowers, squeaky cheese curds, fresh meat and poultry products, homemade baked goods, and local honey, jam and maple syrup — this market has a little bit of everything to purchase and enjoy locally.

Live Music at Capital Brewery & Bier Garten, 6 to 10 p.m., every Friday through Oct. 6

On Friday nights, head to Capital Brewery for a refreshing brew and live music in the Bier Garten. Music starts at 6 p.m., but patrons are welcome to grab a beer and one of the many picnic tables in front of the performance stage beforehand. Guests are also encouraged to bring food in from one of Middleton’s many restaurants or enjoy vendors and food trucks when available on-site.

View the 2023 Capital Brewery Bier Garten music lineup here.

Summer StoryWalk®, June 10 through Aug. 27

Enjoy a story outdoors and downtown with the Middleton Public Library’s summer StoryWalk®, “Jabari Jumps.” Running through Aug. 27, this free activity takes children on a 22-stop reading adventure through downtown Middleton. Maps can be picked up at the Middleton Public Library or downloaded online.

Trivia Night at Stone Horse Green, 7 p.m. every Thursday in June

Put your knowledge to the test by competing in Outdoor Trivia Night at Stone Horse Green at 7 p.m. every Thursday in June at Stone Horse Green in downtown Middleton, an outdoor green space. This free trivia event encourages teams of all sizes to participate. The winning teams for first, second and third place receive gift cards from downtown Middleton businesses.

Live Music at Stone Horse Green

Starting mid-July on Thursday and occasionally Saturday nights, including July 29 and Aug 19, visitors and community members are invited to Stone Horse Green for live music performances. Guests can enjoy downtown Middleton’s beautiful green space while listening to live music. Various music genres are scheduled to perform this summer; visit Stone Horse Green’s event calendar for the most up-to-date music schedule.

June

Prairie Chase Run/Walk & A Celebration of Trails, 8 a.m. to 3 p.m., June 24

The Friends of Pheasant Branch Conservancy, the City of Middleton Parks & Recreation and the Dane County Parks are putting on an all-day, trail-centric celebration at Peasant Branch Conservancy in Middleton. There will be a 10K/5K run/walk starting at 8 a.m. and family-friendly activities to celebrate National Trails Day in the afternoon. Learn more here.

July

Drums on Parade 2023, 7 to 10 p.m., July 1

Enjoy live music over the Fourth of July weekend with stellar marching music performances at Middleton High School’s Otto Breitenbach Stadium. From 7-10 p.m. on Saturday, July 1, the Drum Corps International regional members will compete at Drums on Parade, the group’s annual regional competition. Learn more here.

Fourth of July at the Pool, 1 to 4 p.m., July 4

If you’re looking for somewhere to cool off in between your Fourth of July celebrations, from 1 to 4 p.m., head on over to Walter R. Bauman Outdoor Aquatic Center for its Fourth of July Pool Party. This family-friendly event features fun games, contests and concession specials that are sure to make a splash with the whole family.

EAA Pancake Breakfast, 7:30 a.m. to noon, July 9

Drive or fly in for the EAA Chapter 93 Pancake Breakfast from 7:30 a.m. to noon on Sunday, July 9, for the annual pancake breakfast at Morey Airport. On top of all-you-can-eat pancakes, attendees can also enjoy eggs, sausage, cinnamon rolls, coffee, milk and orange juice. There will also be planes and first responders’ vehicles on display. Tickets are $10 for adults and $5 for children.

Bogey Boogie -Annual Golf Outing, July 19

The Middleton Chamber’s Bogey Boogie Golf Outing is an annual event held at Pleasant View Golf Course every July. This event begins at 10 a.m. and will welcome more than 300 golf enthusiasts to compete in 18 holes of golf. Registration for this event is full, but those interested can put their name on a waiting list. 

Summer Shop & Stroll, July 20-23

Get your shopping shoes on and head to downtown Middleton for a weekend of sidewalk sales, trunk shows and food and drink specials. There will also be programming throughout the weekend at Stone Horse Green. Enjoy live music at 5 p.m. on Thursday, July 20, and a 15-minute “shopping-style” yoga class at 9 a.m. on Saturday, July 23. Learn more here.

Rock the Ramp, 5 to 10 p.m., July 21

Come Rock the Ramp at Capital Flight from 5 to 10 p.m. on Friday, July 21. This free event takes place at Morey Field in Middleton and is the world’s largest pre-OSH (Oshkosh Air Show) fly-in bash. There will be planes, food trucks, an aerobatic airshow, live music, silent auctions, raffles, family-friendly activities and a surprise evening close-out event. All proceeds from the auction benefit the Badger Honor Flight.

August

National Mustard Day, 10 a.m. to 4 p.m., Aug. 5

The National Mustard Museum in downtown Middleton paints the town YELLOW every year on National Mustard Day (always the first Saturday in August). They have planned many fun activities, games and live music this year. This quirky festival is family-friendly and lasts from 10 a.m. to 4 p.m.

Cruise-in, 10 a.m. to 3 p.m., Aug. 12

Enjoy an auto show like no other at Capital Flight’s third Cruise-In. This event takes place from 10 a.m. to 3 p.m. at Middleton Municipal Airport; all proceeds are given to Cars Curing Kids, a pediatric research fund at the American Family Children’s Hospital in Madison. There will be food trucks, live music, family-friendly activities, judged awards, a silent auction and plenty of planes and cars to view.

Roll & Stroll for Pancreas Cancer, 8:30 a.m. to 2 p.m., Aug. 13

Grab your running shoes, walking sticks, set of wheels, or whatever you’d like – Roll & Stroll is back for its 10th annual fundraising event for Pancreas Cancer. To register and participate, choose your course type (walk, run or bike) and create a fundraising goal. There will be a post-event celebration with live music, food, raffles and games.

Good Neighbor Festival, Aug. 25-27

Middleton’s longest-running festival, Good Neighbor Festival, is back for its 60th year. This two-day celebration features a carnival, 5K run/walk, parade, art fair, live music, food and more. Each year, this festival raises money to fund programs in the area and is 100 percent organized and run by volunteers. This year’s theme is “Diamond Jubilee.”