Trail rides

The weather has been very nice lately, though generally after work it is still dark by the time I get out to Cupid.  So on the weekends I try to take advantage of the daylight, and the last two days Cupid and I were able to go on mini trail rides before short arena sessions.  Hopefully this keeps him more interested in his work! 
On Saturday it was a little windy, and he was a little nervous about something which I think was the wind in a tree.  He stopped and hesitated a few times but I was able to get him to walk past it.  We rode past where he once saw the person cleaning the gutter on the ladder and I think he was expecting it again because he was a little nervous but walked by it then was fine.  I just wanted to do a brief canter in the ring after our little trail ride, not realizing that there were a few jumping lessons going on.  They were jumping courses so the rest of the horses pretty much had to stay on the rail.  Luckily Cupid is not distracted or disturbed by other horses flying by.  We did a little walk-trot, then picked up the right lead canter for about a lap.  Then a little more walk-trot, while I tried to decide if it was worth trying to get the left lead with all the other horses around.  I decided to go for it and we got it on the second try!  I always try to give him a lot of praise when he gets it.  We went about once around on the left lead, then a big pat and told him he was done.
On Sunday we went on a slightly different path.  We went down the trail along the electric fence that Cupid has always been scared of.  He was hesitant again and I had to tap him every few steps when he would stop, but eventually we got down the scary trail.  Originally I thought it was the fence, but I think he just doesn't like that the trail is down hill with tall bushes on either side, somehow it's scary for him.  It is just a short keyhole shaped trail, on a clear day you can see all the way to the ocean.  At the end by the key hole there is a pile of old straw, but Cupid walked right by that without even a look.  We trotted a bit and then galloped up the little hill.  It felt awesome!  Though Cupid did get a little tired by the top.  We then walked around the property a bit more and finished up with walking and trotting some figures and circles in the sand ring outside.  I dismounted and Cupid decided that he should be the once to carry the crop.