Golf courses are great places for bluebird trails as long as they do not use pesticides. You might check with a local golf course and see if they would allow boxes to be placed on the edge of the course. I maintain a trail in a local state forest. It has enough cleared land to provide habitat for bluebirds. Our local Master Naturalist chapter meets at the forest and is funding more boxes for the trail this year and next year. Check with your local Extension Office and see if they have room for a bluebird trail.

David, 3 of my trails are located in parks in my county. Yes, you absolutely must get permission . . . there is usually a process of filing your proposal and having it formally approved. It's a good idea to keep a copy of the approval with you during your monitoring visits, too, in case someone questions your involvement with the nestboxes. I keep a copy in my monitoring notebook along with emergency telephone numbers for the police, parks department and wildlife rehabber, just in case.
I also have a small trail with 5 boxes at a local elementary school where I work. I would suggest starting small--maybe a few boxes--and add to your trail a little at a time. During nesting season each box will need to be monitored a minimum of once per week--I usually visit mine 2 to 3 times per week from April through August. It's a huge commitment, but well worth the effort.
Kathy

Thank you organicgardener and Kathy. I greatly appreciate your ideas.

~David

David, it's a GREAT time of year to be thinking about this! See link below with tips on starting a trail. You might think about "adopting" an abandoned trail if there are any in your area - lots of times boy scouts, etc. put up a trail and it is not monitored, which GREATLY reduces the chances of any successful native bird reproduction. Also, sometimes there are older folks who can't handle a trail anymore who need a successor. You might check with the MA Bluebird Society (a good group to join too!!!) See http://massbluebird.org/. If you would like to check out an existing trail, I am in NE CT (and have several) and also have a friend with an awesome Tree Swallow "trail" in her backyard.

Here is a link that might be useful: Ten steps to a bluebird trail

Thanks Bet, never thought of using an already existing trail! I could definetely do that... There is a trail that is in the State Park behind my house that I ride my bike to often. It doestn't look like anybody monitors it, and there are at least two mating pairs of Bluebirds that I noticed over the summer. And thank you for that site, I'm very interested in joining.

Hi David along with bet you have another neighbor here in NE. My trail
runs north to south along a powerline and my trail is 20 years old this spring.
I manage Purple Martins as well. Here in RI and In Rehoboth MA. I manage
two Country clubs that have Martins I dont allow bluebirds there because of
pesticides. But the Martins and tree Swallows do just fine.
As we all know the bluebird is very common today but can always use help
Any clear cut area away from people is prime for bluebirds Powerlines,gas lines
there must be perches for the birds to hunt bugs from and grass should be short. The odds of getting bluebirds high they winter here. My trail is in
northern RI and I produce hundreds of Bluebirds a year.
Ray

Thanks Ray. You seem like an extremely experienced birder. Keep it up.