Summer In The Park 2026

Hello everyone!

In my recent blog post about events in Stamford this summer, I mentioned that there was still one more that I needed to talk about, so now I am going to talk about it!

Before I get into it, I’m going to talk about another summer event that used to happen in Stamford Downtown called Alive At Five. 

As its name suggests, Alive At Five was an outdoor summer concert series on Thursdays that would start at 5:00, except that is not actually when the headliner would start performing, as they would go on stage MUCH later, which I am saying from experience. The series went for so many years, and got so many artists that fall under the categories of artists you have never heard of, and artists you used to hear from, but not anymore. In other words, the type of people who either have been on or are going to be on The Masked Singer. Yes, I can tie so many things back to The Masked Singer. 

These concerts were held in Columbus Park in Downtown Stamford, and they proved to be very beneficial for the city, as there are also many restaurants in Columbus Park, so not only did many people come out to these concerts, they also got dinner from any of the restaurants in the area. Unfortunately, this popularity proved to be the downfall of Alive At Five.

Okay, I don’t actually know how much truth there is to that statement, but I’m going to do my best to explain what I mean. 

While it brought so many people to Columbus Park every summer, it’s not exactly the biggest place in the world. And it would always get so crowded. 

When it returned in 2021 following the pandemic, it had moved to a different location: Mill River Park. I am positive that the main reason for this change was because of the pandemic, which was still going on at the time, and having it in Columbus Park would have been a massive superspreader, while Mill River Park is much bigger and more open. It continued in Mill River Park for three more years afterwards, but there was one thing that couldn’t be ignored. With the move to a bigger park, it was no longer surrounded by any local businesses or restaurants, so people who went there would be getting food from the vendors, as they would want to get to the park by a certain time, and if they got dinner at any of the surrounding restaurants, they would certainly be late. 

During its final year, 2024, the number of shows, which had been reduced to five in 2018, and four in 2021, was reduced yet again to three, and rather than doing the traditional lineup announcement video, they were announced in a single social media post with little to no fanfare. In hindsight, this should not have made it surprising that the event was cancelled after that year.

Around the same time, another big event in Downtown Stamford had been starting up, also in Mill River Park, and also featuring performers on the same level as Alive At Five: The Hey Stamford Food Festival. It has featured such notable names as Tone Loc, winner of The Raspiest Voice I Have Ever Heard, Nelly, The King Of Early 2000s Rap, unless there is someone better than him, because I am NOT familiar with Early 200s Rap, and DJ Pauly D from Jersey Shore, and I feel that saying his claim to fame is enough of an insult towards him.

Here’s an additional fun fact about one year at The Hey Stamford Food Festival. In 2022, two of the headliner performers were Flo Rida and Vanilla Ice. Okay, let me just say this right now, I went through so many jokes in my head about what I could say right here about the two of them, but unfortunately, none of them came together when I was trying to write them. So, I’m just going to say that the joke writes itself, and that performing here is way better than the two of them deserve these days.

At a certain point, however, I feel like they started putting more effort into getting performers for The Hey Stamford Food Festival than Alive At Five, as in 2024, Alive At Five had Sublime With Rome on their farewell tour, rapper Lil Kim, and Wyclef Jean, while The Hey Stamford Food Festival had A Boogie Wit Da Hoodie, by the way, if you want to laugh, just imagine hearing my voice saying that name, and they also had 50 Cent, a man who has achieved a level of pettiness that not even Tom Petty thought was possible.

After they announced that Alive At Five would not be returning again, I assumed that was it for summer concert series in Stamford Downtown, and when I saw that another one was in the works, it would be at least several years before it got started. 

Long story short, Summer In The Park kicked off the very next year. And to say that they had an amazing lineup would be an understatement, as they had Busta Rhymes, Aly & AJ, The Lox, Bow Wow, and Mariah The Scientist. Fun fact: Soulja Boy was going to be part of the event last year, but he dropped out, and was replaced by The Lox. I have no idea why this happened, but if I had to guess, he has the ability to see into the future, knew that he was going to be arrested a few weeks after his show was scheduled, and he didn’t want Stamford to have a performance from someone who was going to get arrested in a few weeks.

The Hey Stamford Food Festival also returned last year, and it was actually part of Summer In The Park. It did not have any notable performers like past years, as I’m thinking they were more focused on getting the performers for Summer In The Park, though they did have a special appearance from Reality TV personality Johnny Bananas.

This is all leading up to me saying that Summer In The Park is back this year, and they have already announced the lineup!

It will be starting on July 16, with a charity concert that will benefit local children’s organizations and help support programs and services that make a direct impact on kids and families throughout the community. The artists who will be performing as part of this will be DaBaby, Fat Joe, and Remy Ma. All I know about DaBaby is that he was featured on one version of the Dua Lipa song Levitating, and has not done much since, and the only Fat Joe and Remy Ma song I am familiar with is Lean Back, and even then it’s only because it was performed on The Masked Singer, and my only other exposure to Fat Joe was on some random game shows and some random movies. Thank you for enjoying today’s episode of Chris Pasquale Has Oddly Specific Knowledge About Pop Culture.

The next show on July 18 is called Perreoland Festival with two reggaeton artists called Jowell and Randy, and the show itself is in celebration of Colombian Independence Weekend.

The next show on July 19 is salsa legends Grupo Niche, and this show is also in celebration of Colombian Independence Weekend.

The next show on July 23 is some DJ duo called Two Friends. I know absolutely nothing about them, but what I do know is that if a DJ duo is performing an outdoor summer show in Stamford Downtown, it’s going to be such a big party. 

The next show on July 30 is a double header of early 2000s R&B/Hip Hop legends: Ja Rule and Ashanti. I actually have additional comments for both of them. If the show stays the way it is, you’re fine, but if Ja Rule starts adding so many other guests and vendors to the lineup and the price of tickets goes up to the point that no average person can afford them, you will be going to Fyre Fest all over again. Here’s what I have to say about Ashanti: She actually performed at Alive At Five a few years ago. I would be more impressed that she is the first person to perform at both Alive At Five and Summer In The Park, but this is only its second year, so I’ll only be impressed if it happens more than once after this year. 

On August 1 and August 2, The Hey Stamford Food Festival will be returning. At this time, I know nothing about it, but if I had to guess, they will not have any big name performers again, but they will have some reality star as a guest there. Like some Real Housewife, or someone from Jersey Shore, or someone from The Hills. I wouldn’t even be surprised if they managed to get Tom Sandoval, who did absolutely nothing wrong, he did what he did for love, which is the greatest motivation ever. That was sarcasm by the way, I do not support what he did at all.

Overall, I would certainly say that Stamford Downtown has a very busy summer coming up, and I’m still impressed that they were able to start up another big summer concert series so soon after Alive At Five ended. I am not entirely sure if I will go to any of these shows due to my unfamiliarity with the artists, but if I do, I will probably go to the outer section of Mill River Park, where I can still hear the music, but not have to buy tickets to get in. For all of you reading, the concerts will be happening on Thursdays, and the two festivals will be happening on weekends, so go ahead and go have a great time in Stamford this July!