What Are the Best Things to Do in Madison This Summer?

By Joshua Holt

Meet Joshua, a licensed real estate professional and accomplished broker. As the forward-thinking leader of the Holt Real Estate Team, he has forged a strategic alliance with Keller Williams and PLACE to deliver on Our Promise.

Summer in Madison offers a wide range of outdoor activities, cultural events, and scenic escapes. Whether you’re a longtime local or visiting for the first time, there is no shortage of ways to enjoy the season. From live music and art to lakeside adventures and culinary festivals, Madison has something for everyone. Here are four top recommendations for making the most of summer in this vibrant city:

1. Concerts on the Square. One of the most popular summer events in Madison is Concerts on the Square. This free outdoor concert series, hosted by the Wisconsin Chamber Orchestra, takes place on Wednesday evenings from late June through July on the Capitol Lawn. It is an excellent way to spend a summer evening, with performances featuring a mix of classical and pop music.

Most attendees bring blankets, lawn chairs, and picnic baskets to relax and enjoy the music in a laid-back, outdoor setting. I recommend arriving early to grab a great spot and checking the orchestra’s website for schedule details and weather updates.

2. Art fair on the square. Held annually on the second weekend of July, the Art Fair on the Square is a juried event that draws approximately 500 artists from across the country. Visitors can explore a wide variety of work, including ceramics, sculpture, photography, and more. The event takes place around Capitol Square, providing a walkable layout that makes browsing and shopping convenient.

I recommend wearing comfortable footwear, bringing a tote bag for any purchases, and staying hydrated to fully enjoy the experience. Whether you’re a seasoned collector or just casually browsing, this event is definitely one you won’t want to miss!

3. Paddleboarding on the lakes. For those who enjoy outdoor recreation, paddleboarding is a standout activity during the warmer months. Madison’s calm lakes and scenic views create an ideal setting for beginners and experienced paddleboarders alike. Local rental services, such as Outdoor UW at Memorial Union, provide easy access to equipment. Paddleboarding offers a combination of exercise, relaxation, and the opportunity to take in unique views of the city’s skyline and natural beauty. Just remember that early morning or late afternoon sessions are best for calm water and lighter crowds.

4. Taste of Madison. Taste of Madison takes place over Labor Day weekend and is one of the city’s most popular food and music festivals. This free event transforms Capitol Square into a vibrant destination for dining and entertainment. With over 80 local restaurants and food vendors offering small plates, it’s a great opportunity to sample new dishes while listening to live music. The event is ideal for food lovers, families, and groups of friends. It runs on August 30 and 31, 2025. To ensure a stress-free visit, I recommend ** ** bringing cash or cards for food purchases, and check the event schedule for live performances to plan your visit accordingly.

These events highlight some of the best ways to enjoy summer in Madison. Whether your goal is relaxation, adventure, or simply making the most of warm weather, there is something here for you. If you need help deciding where to go or what to do, I’m happy to assist. Call me at 608-345-6594, email me at jdholt@kw.com, or visitwww.holtrealestateteam.com to get started. Enjoy your summer!