Make it feel like your party
We start with your must-play songs, favorite styles and guest list—never a one-size-fits-all playlist.
Pleasantville, New York · Westchester Entertainment
Wedding DJs, Sweet 16s, Parties & Photo Booths in Pleasantville
The best parties feel personal, whether you're celebrating with 40 guests or a room full of family and friends. From weddings and Sweet 16s to birthdays, anniversaries and backyard gatherings, Westchester Entertainment brings great music, clear announcements and lively dance-floor energy—without making your event feel bigger or more complicated than it needs to be.
Check Your Date →Your celebration. Our passion.
Whatever the occasion, make it a night to remember.
A first dance, a Sweet 16 entrance, a milestone birthday toast or your favorite song with your closest friends—these are the moments people take home. In Pleasantville, we shape the music, sound and flow around your guests and your setting. You get a celebration that's comfortable, personal and full of life, not a one-size-fits-all show.
Wedding DJs
Polished introductions, meaningful first dances and a soundtrack that brings generations together.
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Sweet 16 DJs
Your favorite songs, dance-floor lighting and the energy to make the night feel truly yours.
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Private Parties
Birthdays, anniversaries and milestones with music that keeps the good times going.
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Photo Booths
Candid laughs, shareable moments and keepsakes your guests will love taking home.
View packages & pricing ↗Why Westchester Entertainment
Personal attention. Professional sound. A really good party.
Let the special moments shine
Clear announcements and thoughtful pacing make room for wedding dances, birthday speeches, cake cutting and everything in between.
Right-sized entertainment
A cozy room and a backyard celebration have different needs. We discuss sound, lighting and setup with your space in mind.
Kind words from clients
Happy clients are our favorite endorsement.
★★★★★
“He has become more than a DJ to us, he is family.”
— Ashley
★★★★★
“The dance floor was packed all night, the energy was perfect, and our guests are still talking about what a great party it was.”
— Wedding client
Local event inspiration
Local celebrations with plenty of personality.
Pleasantville Manor offers a smaller banquet setting, with other venue options in nearby Chappaqua, Briarcliff Manor and Tarrytown. Whether you're planning a wedding, Sweet 16, birthday or family party, we think through the room, sound levels, announcements and dance-floor space with you. The goal is a setup that feels right for your event—not more equipment than you need.
The Pleasantville Manor
110 Nannahagan Road, Pleasantville, NY
Sunlit banquet room and covered terrace on Pleasantville Country Club grounds.
Explore the venue ↗The Kittle House Inn
Nearby venue11 Kittle Road, Chappaqua, NY
Nearby historic inn with dining and event spaces for weddings and private parties.
Explore the venue ↗The Briarcliff Manor
Nearby venue25 Studio Hill Road, Briarcliff Manor, NY
Nearby manor venue with indoor and outdoor celebration settings.
Explore the venue ↗Tarrytown House Estate
Nearby venue49 East Sunnyside Lane, Tarrytown, NY
Nearby historic estate and hotel with multiple wedding and reception spaces.
Explore the venue ↗Venue suggestions are for planning inspiration, not a statement of affiliation or previous performances. Confirm outside-vendor policies, event availability and current terms directly with each venue.
Helpful answers
Questions about entertainment in Pleasantville
Do you DJ weddings, Sweet 16s and birthdays in Pleasantville?
Yes. We plan music and announcements for intimate weddings, teen celebrations, milestone birthdays, anniversaries and other private parties.
What if our party is at home instead of a banquet hall?
We can discuss home and backyard events, including space, power, weather protection and the neighborhood sound environment.
Can we book a DJ and photo booth together?
Yes. Ask about combining DJ entertainment with a digital or print photo booth to give guests another fun way to remember the night.
Check your date
Let’s make your Pleasantville party feel like you.
Tell us what you're celebrating, your date and the music you love. We'll help you choose the right DJ, MC and photo booth options for your guests. Serving Pleasantville, Chappaqua, Briarcliff Manor and Hawthorne.