Greenwich’s Top-Rated Obstacle Course Rental Company
Giant inflatable obstacle courses for birthday parties, school field days, corporate events & more — delivered and set up by our crew. Serving Greenwich, CT and all of Fairfield County.
Inflatable Obstacle Courses for Greenwich Events
Nothing gets kids (and adults!) more excited than racing through a giant inflatable obstacle course. Greenwich families and event planners choose Stevie D Entertainment for Old Greenwich beach parties, Cos Cob neighborhood events, backcountry estate birthdays, Riverside community gatherings, Bruce Park picnic celebrations.
Our obstacle courses feature climbing walls, tunnels, squeeze-throughs, slides, and pop-up obstacles that challenge participants of all ages. We deliver to Cos Cob, Old Greenwich, Riverside, Backcountry, Byram and set up at locations like Tod’s Point (Greenwich Point), Bruce Park, Binney Park. As one of the wealthiest towns in America, Greenwich hosts spectacular private events year-round, and our premium bounce houses fit right in with the celebrations.
Obstacle Course Options for Greenwich

40-Foot Venom Obstacle Course
Our most popular rental in Greenwich! This massive 40-foot inflatable features dual lanes for head-to-head racing with climbing walls, tunnels, and a giant slide finish. Perfect for Old Greenwich beach parties and competitive fun.

30-Foot Radical Run Obstacle Course
A compact powerhouse of fun! The 30-foot Radical Run packs climbing, crawling, and sliding into a smaller footprint — ideal for Greenwich backyards and tighter event spaces near Tod’s Point (Greenwich Point).
Who Rents Obstacle Courses in Greenwich?
🎂 Birthday Parties
Make your Greenwich birthday unforgettable! Kids love racing friends through tunnels and over climbing walls. Our obstacle courses are the ultimate birthday party attraction in Cos Cob and beyond.
🎓 School Field Days
Greenwich schools count on us for field day entertainment. Obstacle courses keep hundreds of students engaged and active — perfect for end-of-year celebrations and PTA fundraisers.
🎯 Corporate Team Building
Companies across Fairfield County book our obstacle courses for team-building events, company picnics, and employee appreciation days. Nothing builds team spirit like a head-to-head race!
⛪ Church & Community Events
Greenwich churches and community organizations love our obstacle courses for festivals, block parties, and fundraisers. We’ve worked events at Tod’s Point (Greenwich Point), Bruce Park, Binney Park and throughout Fairfield County.
Ready to Race in Greenwich?
Join hundreds of Greenwich families, schools, and organizations who trust Stevie D Entertainment for safe, clean, on-time obstacle course rentals. Book today and bring the excitement to your next event!
Obstacle Course Rental FAQ — Greenwich, CT
How much space do I need for an obstacle course?
Our 40-foot course needs approximately 45×15 feet of flat space, and the 30-foot course needs about 35×15 feet. Most Greenwich backyards and event spaces work perfectly. We’ll help you pick the right size during booking.
Where do you deliver in Greenwich?
We deliver to all of Greenwich — Cos Cob, Old Greenwich, Riverside, Byram, backcountry estates, and everywhere in between.
Are obstacle courses safe for kids?
Absolutely! All our inflatables are commercial-grade, fully insured, and sanitized before every rental. We include safety mats and anchoring. Our team does a full safety check at setup. Recommended for ages 5 and up.
How far in advance should I book?
Greenwich families plan ahead! We recommend booking 3-4 weeks in advance, especially for spring and summer events.
Can adults use the obstacle courses?
Yes! Our obstacle courses support participants up to 200 lbs. They’re a huge hit at corporate events, school fundraisers, and family parties in Greenwich where parents want to join the fun.