Looking into boarding options for my next dressage/eventing competition horse, ideally within 30 minutes of East Madison. Good care, grass herd turnout when available, stall or rough board, around 500-600/month or less. Allows outside trainers with insurance. Jumps available. Regarding barn hours - I am a working ammy with typical hours who needs to ride before work fairly frequently. Please PM or comment with any suggestions 
There are likely several places that can meet your requirements, but these are two off the top of my head. I’ve boarded at both and these are long-time owners.
Randy (Saddleridge) and Dave’s (Green Meadows) both have an indoor, outdoor, jump field, and access to the same private trail system and cross country courses. Both offer stall (pasture turnout) and field board.
Randy grows his own hay. The hours are flexible. There are some trainers there but you can also bring in your own. Some information may be found online.
Dave’s place is similar, at least it was when I boarded there. But it’s a little busier with more stalls, two indoors, etc. Dave’s place has a website.
Depending on how far east you are, they may be outside your 30-minute drive window.
Happy to answer questions. Good luck with your search!
We live in Lake Mills and this is a beautiful barn. I don’t know much else about it though.
Apologies for piggybacking off OP - I have also been in search of (seasonal) boarding in the Madison area for this coming summer, looking for any barns that could accommodate a few extra from July-October coming up from Florida. Pasture board would be fine - two field hunters and a retiree. Would appreciate any ideas! 
I have boarded at both, and am looking for a bit smaller facility than either of those two. Ideally horses would be hand led in from turnout and not running loose across concrete.
To clarify on the hours, I am looking to be able to take 7 am lessons with my trainer before work
Randy’s has had seasonal boarders in the past. Dave might possibly allow it too. The only two other places I can think of that have pasture board are Felix Jaramillo in Sun Prairie but there may be a training requirement, and Snapdragon out in Mt Horeb. I’m not at all familiar with the latter (friend of a friend).
If you’re familiar with the area, then you probably already know most of the barns. Your criteria list isn’t long by any means but many of the barns have open hours that aren’t conducive to riding before normal business hours. Maybe a private barn would be more flexible? Most of the private barns with which I have experience have since changed owners, so I won’t be much assistance there.
I’ve been discovering that hours are going to be an issue at most barns. If barn hours were 6:30 AM - 9 PM, that would be very doable for me.
I live in Sun Prairie/East Madison. I’ve been in the area for a while and am basically looking for the places that I am not already aware of.
Thank you! I have checked with Green Meadows and unfortunately they aren’t able to accommodate for seasonal, I will reach out to the others!
I am local to you and also don’t know of better options than ones that have been brought up. I had found my perfect farm 11 years ago and stayed for a decade until the owners decided to sell, so now I board at a friend’s house.
If you have 2.4 million dollars though, I can point you to a really choice horse property for sale!
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