Summer Vibes in Main Street Madison
Jen DeLessio
Executive Director
Main Street Madison
Thank you to our Main Street Madison volunteers, the City of Madison, and our outstanding community for supporting our inaugural downtown block party, A Taste of Downtown, on May 16th! We couldn’t have asked for a better kickoff to the season. We had gorgeous weather, incredible live music, and our local restaurants served up delicious food. The energy was fun and relaxed with a perfect combination of regular downtowners along with new visitors discovering the charm of the district for the first time.
We completely sold out of tickets for this inaugural event! If you missed the opportunity for this food stroll, please stay tuned for the next one, as we are already brainstorming one for the fall! A massive thank you goes out to Main Street Cafe, Zanotta’s, Vine & Oak, Lanier House, and Old Black Bear for collaborating on this genius event - we can’t wait to showcase more fabulous dishes at the next Block Party. We also want to extend a huge thank you to our Presenting Sponsor, New Leaf Counseling, and all of our Supporting Sponsors. Main Street Madison is grateful for such a supportive community!
In case you missed the block party, Main Street Madison also unveiled a brand-new collection of outdoor games for the community, affectionately called Tom’s Toy Chest. Designed to bring some playful energy to our downtown, this collection includes oversized outdoor games including: Connect 4, Jenga, Corn Hole, Chess, and Yard Pong. Tom’s Toy Chest is named in honor of Senator Butler for his decades of service and dedication to historic downtown Madison, serving as a wonderful reminder of his legacy of bringing people together.
To our local community groups - please reach out to me to discuss the use of Tom’s Toy Chest for your upcoming events! We want these games to be loved and used! You can look for the Toy Chest in action at the upcoming Parrot’s Block Party at Home Place Park on June 6th, and also at several America 250 events this summer across Madison.
Did you know the 2026 Summer Solstice is June 21st and the longest day of the year? As it turns out, you don't have to wait until the 21st to celebrate the peak of summer sunshine. June 18th is only 14 seconds shorter than the solstice, and it just happens to be the first night of our annual Third Thursdays on Main presented by Madison Hospital! There will be 14 and a half hours of daylight on the 18th, making it an amazing, glowing night for live music, shopping and dining downtown, and for checking out our Third Thursday vendor lineup.
What’s new for 2026? This year’s Third Thursdays will begin a new tradition - Sips of Summer! Participating businesses throughout downtown will offer sips of their favorite summer drink recipes. Look for signs that highlight their participation as well as drink specials in our restaurants. And please don’t forget that Main Street Madison is an official Entertainment District! This means that you can purchase your favorite beverage from Main Street Cafe, Zanotta’s, Old Black Bear, Vine & Oak, or Lanier House, and stroll around the district with a green cup in your hand.
There will be live music in the Courtyard (in front of Old Black Bear), with a mix of vendors set up throughout downtown, including Garner Alley and the private drive next to Filthy Gorgeous. Look for lots of colorful tents, unique local crafts and goods, and friendly faces! Be sure to check our website and social media pages as we make announcements regarding our live musicians, food trucks, and the designated kids' zone.
Third Thursdays on Main! – Main Street Madison
Join the Main Street Team: We Need You!
As we look ahead to a busy summer, please remember that events don't just happen! They are fueled by the generosity and time of our incredible volunteers. Whether it is helping to hand out tickets, assisting vendors with setup, monitoring the kids' zone, or helping keep our historic streets clean, our volunteers are the true backbone of Main Street Madison.
If you love our community and want to get involved, we would love to have you join the Main Street Madison crew! We work together to support our local small businesses from behind the scenes, and play a direct role in making downtown Madison a fun place to be. We have opportunities available for the upcoming Third Thursdays series on June 18th, July 16th, and August 20th, as well as events throughout the year. If you are interested in volunteering for even just a couple of hours, please either fill out our website form, or contact me directly to find a role that fits your schedule and interests.
Get Involved – Main Street Madison
If you haven’t visited Main Street Madison before, or if it’s been a while, please come see us this summer! Downtown events are meant to bring our community together while supporting our small businesses. We can’t accomplish either of these things without you. Grab your family, your friends, and we will see you on June 18th!