I never even tried taking my kids to a regular barber/salon for their first haircut. I had heard about Snip-Its and while it can be a little over the top for the parents, the kids love it. And it really isn't that much more expensive than say, a SuperCuts. I have been to the one in Chestnut Hill [M-Sat 9-6, Sun 10-5], but there are also locations in Framingham, Canton and Burlington. They even have Birthday parties that run about $20 per kid plus a $30 party fee - but I have never been to one. They do have a lot of toys available for purchase, so if you end up having to wait for a while, that can get annoying because of course your kids want them....
Prices: [Mar 05] $15.95 for a haircut, $6.95 for a bang trim, $9.95 for a buzz cut