New Canaan’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 New Canaan, CT and all of Fairfield County.
Inflatable Obstacle Courses for New Canaan Events
Nothing gets kids (and adults!) more excited than racing through a giant inflatable obstacle course. New Canaan families and event planners choose Stevie D Entertainment for Waveny Park birthday celebrations, Silvermine neighborhood gatherings, estate backyard parties, school carnivals at South School, community events at Mead Park.
Our obstacle courses feature climbing walls, tunnels, squeeze-throughs, slides, and pop-up obstacles that challenge participants of all ages. We deliver to New Canaan Center, Silvermine, Ponus Ridge, South Avenue area and set up at locations like Waveny Park, Mead Memorial Park, Irwin Park. Waveny Park alone hosts hundreds of family events each year. New Canaan families love creating memorable party experiences in their beautiful outdoor spaces.
Obstacle Course Options for New Canaan

40-Foot Venom Obstacle Course
Our most popular rental in New Canaan! This massive 40-foot inflatable features dual lanes for head-to-head racing with climbing walls, tunnels, and a giant slide finish. Perfect for Waveny Park birthday celebrations 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 New Canaan backyards and tighter event spaces near Waveny Park.
Who Rents Obstacle Courses in New Canaan?
🎂 Birthday Parties
Make your New Canaan birthday unforgettable! Kids love racing friends through tunnels and over climbing walls. Our obstacle courses are the ultimate birthday party attraction in New Canaan Center and beyond.
🎓 School Field Days
New Canaan 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
New Canaan churches and community organizations love our obstacle courses for festivals, block parties, and fundraisers. We’ve worked events at Waveny Park, Mead Memorial Park, Irwin Park and throughout Fairfield County.
Ready to Race in New Canaan?
Join hundreds of New Canaan 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 — New Canaan, 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 New Canaan backyards and event spaces work perfectly. We’ll help you pick the right size during booking.
Where do you deliver in New Canaan?
We deliver throughout New Canaan — the Center, Silvermine, Ponus Ridge, and all residential neighborhoods. Professional setup always included.
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?
New Canaan events book quickly. We recommend reserving 3-4 weeks ahead, particularly for Waveny Park-adjacent parties in warm months.
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 New Canaan where parents want to join the fun.