
PHOTO BY JONATHAN CUNNINGHAM
Residents of Westchester and the surrounding area should put on their dancing shoes and get ready for the return of one of the region’s most popular summer events: The Pleasantville Music Festival, slated for Saturday July 13th. Now in its 18th year, New York’s Backyard Jam, sponsored by Northwell Health, brings together 18 musical acts and curates them on three stages for a day and evening of great tuneage at the Village’s Parkway Field.
Of the Festival’s three stages, the largest is the Main Stage. It is set in the middle of Parkway Field, and it’s where the national acts generally play. This year’s just-announced musical line-up includes Brooklyn indie rocker Margaret Glaspy; reggae royalty, The Wailers; West Coast ‘roots rockers’, The Record Company; and 90’s mega hit-makers, Better Than Ezra.
Not far from the Main Stage are both the Chill Tent Stage and the Party Stage. Each becomes active between acts on the Main Stage. The Chill Tent is where the music and temperature both tend to be a bit cooler. It’s here that you’ll find more acoustic and softer music, tucked away from both the elements and the hustle and bustle of the main field. This year, Chill Tent stage artists include endearing singer/songwriter, Jesse Terry and the stage’s headliner, witty and engaging folk-rocker, Jill Sobule. The Party Stage is where you’ll find vibrant, younger acts working to get the crowd pumped up and dancing. This year it will be headlined by The Collection, an alt-pop band out of North Carolina. The line-up on these stages will be supplemented by a host of local and regional artists, all adding up to a full day of great music for all.
According to Festival Director Bruce Figler, having variety is key. “Musically, we really try to have a little something for everyone. We know that we attract many different age brackets, along with a wide range of music tastes, so we try to check off as many boxes as we can.”

PHOTO BY JONATHAN CUNNINGHAM
Even though it’s called a Music Festival, it is much more than that. There’s the Captain Lawrence Beer & Wine Garden with an array of adult beverages for those 21 and over. Hungry? A Food Court features delicious selections for all tastes and palates (Outside food is permitted to be brought in, but outside alcohol is not permitted). You can take a break and browse the Festival’s Vendor Village featuring crafts and other unique shopping opportunities. And since children under 12 get in free, there are plenty of kids’ activities to keep them busy, such as the Kid’s Zone with rides, games, and face painting. There will also be a noon time music performance for kids in the Chill Tent. With all this going on, you might be surprised to learn that the Festival is run mostly by volunteers.
Getting to Parkway Field is easy. Those who live nearby, can walk or ride their bikes there. Those who come from away, can arrive by Metro North, Beeline bus, or by car. Parking is free at nearby Pace University with a quick and easy, free shuttle to get attendees to the field.
According to Figler, “It’s kind of a pop-up backyard party, complete with lawn chairs, blankets and friends. And even though we bring in some big-name acts, the Festival retains its small town charm. It’s a very manageable event. I like to think of it as the music festival for people who like the idea of music festivals much more so than the realities of many of the festivals out there.”
Unless attendees have reservations in the Festival’s popular Tent City area, tents and umbrellas are not permitted on the field as they block the sightlines of people seated behind them. Those that wish for a respite from the elements can find refuge within the Chill Tent or under the large Shade Tent towards the back of the main field.
Gates open on July 13th at 11 a.m. with the first act starting at noon. The music usually finishes by 9:30 p.m. The Pleasantvile Music Festival is a rain or shine event. For tickets or more info, go to PleasantvilleMusicFestival.com.
When given the opportunity to visit the 17th annual Pleasantville Music Festival on behalf of the Inside Press, I had to take it! For years, my family has been invited but scheduling issues always arise, and bummer after bummer, for one reason or another, it just didn’t work out! So that I was excited is an understatement given what I already knew about the Festival’s diverse offerings. When I entered, I noted the three performance stages, countless food tents where friends and families gathered for both shade (yes, it was a hot summer’s day) and a really good meal, in coolers from home or purchased. The total picture for me shouted “great family experience”!
I have a little announcement to make. After 25 years of Chappaqua living, I’m downsizing and moving this month to Pleasantville! I look forward to discovering the joy of a Mount Pleasant residency and all its treasures, to meeting new neighbors, and making new friends. I’m also viewing it as a boon to getting more fit as I’ll be just that much closer to two favorite walking destinations, the Rockefeller Preserve and Rockwood, and also to Club Fit in Briarcliff (where, note to self, I really MUST start reserving class time). I’ll also be closer to the upper West Side where my son lives, not to mention dear friends. Life is good.






For a village of just 7,000, Pleasantville has a remarkably strong collection of dining options. A few of my newer favorites: Pub Street for seafood and salads, Mission Taqueria for tacos and margaritas, Southern Kitchen for, well, southern food, and Dai for its fresh sushi, soups and charming atmosphere. I get the sense Pleasantville residents don’t have a restaurant saturation point, which is good news for those of us who live here. If somebody builds a good one, they will come.
We all need to hit the Westchester or the Palisades Center on occasion. And I don’t want to see any of those stores go out of business. But when I have to buy a gift, I stay in town. I like pulling right up, throwing a quarter in the meter and walking into the Glass Onion for jewelry and accessories, Rhododendron for scarves and other women’s gifts, Aardvark for the dog, Kimberly House for baby clothes and scented gifts, Photo Works for a framed photo for the grandparents, and of course back to the Village Bookstore for anyone. Tip: The Pleasantville Pharmacy is a great stop at Christmas for something extra for kids, a pair of earrings, or a hostess gift.
I live in a mid-century modern home, and I’m not alone. A friend owns one near town where I’ve seen several, and then there’s Usonia, Frank Lloyd Wright’s utopian dream, right here off Bear Ridge Road. If the 1950’s are too new for you, Pleasantville has an impressive stock of Tudors, Victorians and Colonials, particularly the beauties lining Bedford Road that help Pleasantville live up to its name.
We’re a Clearwater Family, but I’ve got to say, Pleasantville is giving the Croton festival a run for its money when it comes to talent. This year, Everclear, Soul Asylum, Aimee Mann and Matthew Sweet were the featured artists. Every year in July, Parkway Field turns one Saturday into an all-day party. You can bring your kids or leave them home, but there’s something for everyone.
One thing I’ve heard consistently about Pleasantville lately is how fiercely proud residents are of their town and of Mount Pleasant at large. As I produced this edition over the summer, and learned about Break the Hold, via Sabra Staudenmaier’s cover story for us, it was not hard to see why.
