Pleasantville Music Festival

If you are looking for a fun and exciting event in Northern Westchester this summer, head over to the Pleasantville Music Festival! This event is a single-day music festival that is held at Parkway Field in Pleasantville in the month of July and features a variety of performers. The event first started in 2005, and has happened every year since, with the exceptions of 2020 and 2021 due to the pandemic. The performers that they get are major acts that are headliners for the event, up-and-coming regional acts, and small local bands from the tri-state area. In this post, I will be going over all the major artists that have performed there over the years and finish off with the artists that were just announced as performing there this year. 

The first festival in 2005 didn’t have as many notable names as following years, but they did have some names that are noteworthy. One of these artists is a country and folk singer named Jonathan Edwards, who is best known for his 1971 song “Sunshine,” which I think is a cool artist to have at an event like this. Another interesting artist they had this year was a band from Sleepy Hollow called The Slambovian Circus of Dreams, which is described as “Hillbilly Pink Floyd” and “Punk Classical Hillbilly Floyd.” I find this to be a bizarre description for an artist, but I think it would make for an entertaining show.

In its second year in 2006, they started to have a few more noteworthy names. They had a performance from Dar Williams, a pop folk singer who is originally from Mount Kisco and was described in The New Yorker as one of America’s very best singer-songwriters. The main headliner they got that year was Roger McGuinn, frontman and leader of the legendary 60s rock group The Byrds. I think it’s great that the event was able to get such an iconic singer in its second year.

In its third year in 2007, the event had two headliners that were folk rock singers. One of them was named Jonatha Brooke, and the other was named Shawn Mullins, whose 1998 single “Lullaby” was nominated for a Grammy Award. It’s great hearing that a Grammy nominated artist has performed in Pleasantville. 

In 2008, the event had two notable headliners. The first was an English new wave rock singer named Graham Parker, who is the lead singer of the band Graham Parker & the Rumour. When I went to his website, I saw that he still tours, and that he recently performed at the Rockland Center for the Arts in West Nyack, Daryl’s House Club in Pawling, and StageOne in Fairfield, so I think it’s cool that he still performs at venues in the area. The other headliner this year was Joan Osborne, a rock singer with seven Grammy Award nominations who is best known for her song “One of Us.”

In 2009, the event only had one major headliner, which was alternative rock band Big Head Todd and The Monsters. They have a Platinum album called “Sister Sweetly,” and they have a considerable following in the Mountain States, which makes sense because they are from Boulder, Colorado. I have also seen that they have performed at other venues in the area in the past, so it’s cool to see that they have performed at an event in Westchester.

In 2010, the event had two notable headliners. The first one was country and folk-rock duo The Bacon Brothers, which consists of Michael Bacon and legendary actor Kevin Bacon. I think it’s incredible that the event was able to get a musical act that consisted of one of the most famous actors. The other headliner that year was Jakob Dylan, lead singer for the rock band The Wallflowers, and the son of legendary singer Bob Dylan. I think it’s cool that they booked an artist that is the son of one of the most famous singers and the lead singer of another successful and famous rock band.

In 2011, the event had two notable headliners. The first one was an indie rock band called Augustana, who are best known for their song “Boston.” The other headliner was folk rock singer Marc Cohn, who won the Grammy Award for Best New Artist in 1992 and is best known for his song “Walking in Memphis,” which is one of my favorite songs, so I think it is cool that he performed in Pleasantville many years ago.

In 2012, the event had two notable performers. The first one was Sloan Wainwright, who is the sister of Loudon Wainwright, and the aunt of Martha Wainwright, Rufus Wainwright, and Lucy Wainwright Roche. I find it great that the event was able to get somebody who is part of a family of singers, and is from the area, as she is originally from Bedford. The other notable performer that year was British new wave band The English Beat, who are best known for their song “Save It for Later.”

In 2013, the event had one headliner, who was a folk singer named Brett Dennen. He has released seven albums, had one of his songs used on the shows “About a Boy” and “Wizards of Waverly Place,” and opened for John Mayer on one of his tours.

In 2014, the event had three notable performers. Indie rock band Augustana returned for a second time. The second notable performer that year was folk rock singer Amy Helm, the daughter of Levon Helm from The Band. I think it’s cool that the event has been able to get so many artists that come from famous families. The third notable performer that year was Ian Hunter, the former lead singer of the rock band Mott the Hoople, who are best known for their song “All the Young Dudes.” I am impressed by the fact that they were able to get such a noteworthy rock singer from the 60s and 70s to perform there.

In 2015, the event had three more notable performers. The first performer was an alternative rock band called Fastball, who have a Platinum album called “All the Pain Money Can Buy” and a gold single called “The Way.” The second headliner that year was a rock band called G. Love & Special Sauce, who are a fusion of blues, hip hop, rock, and soul. The third headliner was alternative rock band Gin Blossoms, who are best known for their songs “Hey Jealousy” and “As Long as It Matters.” They have also performed at the Pound Ridge Harvest Festival and Alive at Five in Stamford, so I think it’s cool that they have performed at three major events in the area.

In 2016, the event had four notable performers. The first headliner was alternative rock band The Smithereens, who are best known for hits from the 80s and 90s, such as “Only a Memory,” “A Girl Like You,” and “Too Much Passion.” They have also collaborated with musicians such as Belinda Carlisle, Lou Reed, and The Kinks. The second headliner was another alternative rock band called The Revivalists, who are best known for their song “Wish I Knew You” and were named by Rolling Stone magazine as one of “10 Bands You Need to Know.” The third headliner was alternative rock singer KT Tunstall, who is best known for her songs “Suddenly I See” and “Black Horse and the Cherry Tree.” She has also done many other shows in the area in recent years, so I think it’s great that she still brings her tours to this area. The fourth headliner was another alternative rock band called Guster, which has performed at the Capitol Theatre in Port Chester in recent years.

In 2017, the event had three headliner performers. The first headliner was Suzanne Vega, an alternative rock and folk-rock singer. She has been nominated for seven Grammy Awards and is best known for her song “Luka.” She has also performed at other venues in the area in recent years, such as The Ridgefield Playhouse, Emelin Theatre in Mamaroneck, and District Music Hall in Norwalk. The second headliner was hard rock band Living Colour. They are best known for their song “Cult of Personality,” and have been nominated for four Grammy Awards with two wins. They are also in my opinion, the only band that will perform there that can be considered hard rock. The third headliner was Blues Traveler, who have performed in the area a lot over the years, performing at venues like the Tarrytown Music Hall and the Capitol Theatre, and at events like the Pound Ridge Harvest Festival and Alive at Five.

In 2018, the event had four headliner performers. The first was an alternative rock band called Cracker, who are best known for their song “Teen Angst (What the World Needs Now).” They also performed at the Pound Ridge Harvest Festival that same year, which I think is cool. The next headliner was a gospel band called Robert Randolph and the Family Band. They have been nominated for four Grammy Awards and Robert Randolph was on Rolling Stone’s list of the 100 greatest guitarists of all time. The next headliner was a folk band called The Lone Bellow, which is from Brooklyn. The last headliner was English new wave band called The Psychedelic Furs. They are famous for many songs, such as “Pretty in Pink,” “Heartbreak Beat,” and “All That Money Wants.”

In 2019, the event had five headliner performers. The first headliner was an alternative rock band from New York City called Bailen, who also performed one of their songs on the Today show that same year. The second headliner was an alternative rock singer named Matthew Sweet, who has done many songs since 1986, and has also contributed music to many TV shows and movies. The third headliner was another alternative rock singer named Aimee Mann. She has been nominated for six Grammy Awards with two wins and has appeared in several TV shows and movies such as “The Big Lebowski” and “Comedy Bang Bang.” The fourth headliner was an alternative rock band called Soul Asylum, who are best known for their Grammy Award winning song “Runaway Train.” The fifth headliner was alternative rock band Everclear, who are best known for songs like “Santa Monica,” “Everything to Everyone,” and “I Will Buy You a New Life.” They also performed at the Pound Ridge Harvest Festival a few months later. I think it’s cool that they performed at two events in Northern Westchester in one year.

The event returned in 2022 with four notable headliners. The first headliner was Paula Cole, a pop rock singer who is best known for her songs “Where Have All the Cowboys Gone,” which was nominated for three Grammy Awards, and “I Don’t Want to Wait,” which was used as the theme song for the show “Dawson’s Creek.” The second headliner was Glenn Tilbrook, the lead singer of the English new wave band Squeeze, who are best known for their songs “Tempted,” “Black Coffee in Bed,” and “Hourglass.” This is also a performance that I know my parents would have loved to see. The third headliner was supposed to be alternative rock band 10,000 Maniacs, but they dropped out close to the actual event and were replaced with Crash Test Dummies. They are another alternative rock band who have been nominated for three Grammy Awards and are best known for their songs “Mmm Mmm Mmm Mmm” and “Superman’s Song.” I am impressed by the fact that they were booked as a replacement at almost the last minute. The fourth headliner was pop rock band X Ambassadors, who are best known for their songs “Renegades” and “Unsteady.” They also performed at Alive at Five two weeks later, and I think it’s cool that they performed at two events in the area in one summer.

In 2023, the event had six headliner performers. The first was Pete Francis, a folk-rock singer who is also the founding member of the alternative roots band Dispatch. The second headliner was Sophie B. Hawkins, a Grammy nominated pop rock singer who is best known for her songs “Damn I Wish I Was Your Lover,” “Right Beside You,” and “As I Lay Me Down.” The third headliner was a psychedelic rock band called Blac Rabbit. The fourth headliner was an indie folk singer named Allison Ponthier. The fifth headliner was a southern rock band called The Allman Betts Band, which consists of the sons of the founding members of The Allman Brothers Band. The sixth headliner was They Might Be Giants, which I feel is a performance that I probably should have gone to see, as my dad has been a fan of them for a long time, and I have enjoyed them since I was a kid.

This year’s lineup has three noteworthy headliners. The first headliner is a Grammy nominated rock band called The Record Company, who are best known for their song “Life to Fix.” The second headliner is legendary reggae band The Wailers, which is made up of former members from the original band with Bob Marley. The third headliner is alternative rock band Better Than Ezra, who are best known for their Platinum album “Deluxe” and their song “Good.”

This event has brought some great music to Northern Westchester, so get your tickets now and go hear some music in Pleasantville on July 13!