Chappaqua's
Party
Rental Experts
From backyard birthday parties on wooded estate lots to school field days at Roaring Brook and Grafflin — Stevie D Entertainment delivers professional inflatables and full event packages throughout Chappaqua and the Town of New Castle.
Chappaqua is one of Westchester County's most distinctive communities — a wooded, estate-character hamlet where century-old Colonials sit on multi-acre lots and community events carry real tradition. The Memorial Day parade down South Greeley Avenue, summer Gazebo concerts at Recreation Field, and field days at Roaring Brook, Grafflin, and Westorchard Elementary all reflect a community that invests deeply in its events.
Stevie D Entertainment has delivered bounce houses and full event packages throughout northern Westchester for years. We understand the long driveways, the wooded backyard setups, and the logistics of working on larger private properties in the Town of New Castle. We show up prepared, professional, and on time — every single time.
- Familiar with Chappaqua's estate lots, wooded properties & long driveways
- Chappaqua Central School District events welcome
- All inflatables deep-cleaned & sanitized before every delivery
- Full delivery, setup & breakdown — zero work for you
- Fully insured — COI provided for venues, schools & parks
- No third parties — we own all equipment, show up ourselves
At a Glance
🌸 Spring and summer weekends book 3–5 weeks out in Chappaqua — especially around the Memorial Day weekend, school year-end parties, and Gazebo concert season. Book early to lock in your date.
Inflatables for Every Season in Chappaqua
Chappaqua has a rich community calendar year-round. Here's how Stevie D Entertainment fits into Chappaqua's most popular event seasons.
- Memorial Day weekend backyard parties
- Roaring Brook & Grafflin school field days
- Westorchard Elementary end-of-year events
- Town of New Castle community celebrations
- Seven Bridges & Robert E. Bell spring fairs
- Backyard birthday parties on estate lots
- Gazebo concert season parties at Recreation Field
- Chappaqua Farmers Market community events
- Camp Adventure & summer program events
- Gedney Park family gatherings & reunions
- Horace Greeley High School fall events
- Ragamuffin Parade & Halloween Carnival
- Chappaqua Children's Book Festival
- Fall birthday parties on wooded properties
- New Castle community harvest celebrations
Everything We Offer for Chappaqua Events
One call covers your entire event — pick a single bounce house for a backyard birthday or build a full carnival package for a school field day.
Classic Bounce Houses
Fits Chappaqua's larger backyard lots perfectly. Colorful, safe, and sized for both small gatherings and full parties.
Combo Bounce & Slide
The summer essential for wooded estate backyard parties. Bounce and slide in one — great for all ages.
Obstacle Courses
A highlight at Chappaqua school field days and PTA events at Grafflin, Roaring Brook, and Westorchard.
Hungry Hippo Challenge
Life-size Hungry Hippos — a massive hit at Chappaqua school carnivals and Memorial Day weekend gatherings.
Boom Box Bounce House
The inflatable that stops the show. Perfect for music-themed parties at Chappaqua Performing Arts Center events and estate parties.
Carnival Packages
Full carnival buildouts — games, concessions, inflatables, and staffing — for large Chappaqua community events.
Estate-Ready Delivery & Setup
Most Chappaqua properties aren't your typical suburban backyard. Long private driveways, sloped wooded terrain, gated entries, and multi-acre lots present logistics challenges that many rental companies aren't equipped for.
We've set up on properties throughout northern Westchester and understand exactly what it takes to deliver and set up safely on Chappaqua's estate-style properties.
Long Driveway Delivery
We assess access routes during booking and bring the right equipment for narrow or gated entries.
Sloped & Wooded Lots
We identify the flattest viable setup area on your property and bring appropriate ground anchoring.
Tree-Canopy Clearance
Our team checks overhead clearance during setup — critical for Chappaqua's heavily wooded properties.
Brand New Equipment Available Now
Our full 2026 fleet just arrived — new themed inflatables, carnival game systems, and specialty equipment available for Chappaqua events this season.
Chappaqua & Northern Westchester
We deliver throughout the Town of New Castle — including Chappaqua, Millwood, and surrounding hamlets — and across all of northern Westchester. Whether your event is steps from the Chappaqua train station, on a wooded lot near Whippoorwill Park, or anywhere in the surrounding area, we deliver prepared.
No out-of-area delivery fees within our service zone. We serve all of Westchester County, Connecticut, and New Jersey.
Towns We Serve Nearby
Everything to Know Before You Book
Yes — this is one of our specialties in northern Westchester. We review your property access during booking. Let us know your driveway length, any gates, and the setup area and we'll confirm the right unit and delivery approach. We bring equipment sized for residential access in Chappaqua.
Events using inflatables at Town of New Castle public parks require a Special Event Permit from the New Castle Recreation & Parks Department. We recommend applying 4–6 weeks in advance for peak-season dates. For private residential setups anywhere in Chappaqua, no permit is needed.
Summer weekends — especially Memorial Day weekend, June, and July — book 3–5 weeks out. The Chappaqua school event season in late May and June is especially busy. We recommend booking as early as possible for any summer or spring date. Call us and we'll check availability immediately.
Yes. Stevie D Entertainment carries full liability insurance for events throughout New York, Connecticut, and New Jersey. We provide certificates of insurance for Chappaqua Central School District events, Town of New Castle parks permits, HOAs, and private venues that require documentation.
Most bounce houses need a flat area of at least 15×15 feet and a standard 110V outlet within 50 feet. For larger Chappaqua estate properties, generator rentals are available if no nearby outlet exists. We review your setup area during booking to recommend the right unit for your space.
Absolutely. We specialize in complete school event packages — inflatables, carnival game midways, concession stands, obstacle courses, foam parties, and staffing. We've run large field days and PTA fundraisers across Westchester and meet all insurance and safety requirements for Chappaqua Central School District events.
Let's Make Your
Chappaqua Event
Unforgettable
Summer and spring weekends fill up fast. Lock in your date today — same-day quotes, no hassle.
