First, the state of CT has a program titled Care 4 Kids, which helps qualifying families with the costs of day care and pre-schools.   Check their website, or call them at 1.888.214.5437 to see if there are any participating pre-schools and or day care centers in your area. 

Whether or not you qualify for the Care for Kids program, you should also ask any school which you are considering whether or not they offer tuition assistance.  Even if they don't advertise such a program in their marketing materials, they may offer one upon request.  Also, a school may also be more willing to offer assistance later in this admission season; for example, if you are enrolling a child in August, the school may be more flexible if they think they are unlikely to get another child to fill that spot. Some of the schools that do advertise tuition assistance are the Landmark Preschool in Westport, the First Congregational Church Nursery School in Darien and the Montessori School in Wilton.  And don't panic when you look at the tuition rates - you never know what sort of financial assistance is available until you ask!

It is also well worth inquiring whether or not your school offers a discount for enrolling more than one child.  Lots of schools offer a multi-sibling discount, and once again, it is worth asking even if the school doesn't advertise the discount.

If you are unable to qualify for any assistance with your tuition, I recommend looking at schools with “a la carte” pricing option.  Toddlertime of New Canaan, for example, offers families a basic package, with the option to add on daily lunch bunches or afternoon classes as you wish.   And finally, several of the local YMCA’s often offer fantastic pre-school programs with slightly more affordable pricetags.  Within Fairfield County, try the YMCAs in New Canaan, Stratford, and Milford for pre-school options.  

My last suggestion?  Lottery tickets.  Good luck!