Maaan, kudos to you to try and get an endless number of rides somehow organized and "in line".
Decades of rides big and small, who was along for which ride, which bike/ jacket/ luggage did he/her use an such + such a trip, when did we go to xxx, there was that river crossing...but where??
And there's 1000's of pics around... all over the bloody place.
Know what you mean...and the "chronicle" bit of the blog indicates the idea of getting some order into things...but Holy Crap, what a job!
In my case, I went with a chronological "listing", adding the year to the trip-titles, then checking back on the picture-dates to stack the listings as per months etc.
Each ride-listing has a few pics (as a visual trigger for myself and those who were along at the time...plus it's nice for a visitor to see what's in store) and a short wrap up to make it easier to identify....and a link to the full story.
This way allows myself and mates to check back and find rides that we've participated in quickly and/ or by some additional hook like :that must've been August, that was 2 weeks before my birthday"....or...."that ride was the first after I bought the DRZ in February '09"...etc.
I find myself using it constantly/ daily as a resource to check back on ride details, pics, bikes, places, folks and a myriad of other things. My friends and riding-mates are doing the same,
the whole thing being searchable by key words/ names/ locations/post-dates etc as well.
Took me about 4 months all up to get the listings done....nowadays I just occasionally update/ add to it with a few rides of the last few weeks at a time...which takes me about 30mins to do the job and about 2 hrs of reading the ride-reports again and gawk at the pics

I'm a sucker for good yarns and photos.
Once you've done it....it becomes invaluable in no time flat!!
Apart from being able to browse the listings, pics and blurbs on a leisurely night and getting stuck reading up on some half-forgotten ride from 15 years ago.
Good luck...just don't forget to add some easy + logical structure that makes it easy for you (and friends, family, riding buddies etc) to find specific stuff on the site/ blog.
Flashy looking stuff gets frustrating quickly... if one can't find it.
And try to pick a site/ format/layout etc to work with that is unlikely to disappear soon or gets merged with other stuff/ a server getting taken over...or superseded software-wise to a point where it's non-transferable into other formats etc. because you don't want to do this a second time around.