Best Century in Your State

My dad signed up the family for a Century Bike ride when I was 13 years old.  When only road to the begals at the first aid station and then came back which put us at about 28 miles.  That is the only charity ride I have ever done so I don't have much insider information on Century rides, but there is the MS 150 in Texas that goes from Houston to Austin.  It is a pretty bike deal and you might consider it if you are okay with doing 150 miles.  :-)   When I lived in Oklahoma I took part in the Free Wheels Bike Tour.  They spend a whole week and ride all the way across the state, but there are options to just do one day and many of the days have century options to ride.

If you're looking for one in Maryland, the Gran Fondo in September is the way to go.  10K feet of climbing with some timed sections:

https://www.bikereg.com/maryland-gfns

Almost all of ours here on in September (I think there are like 4 that I know of, and the other three are flat).

Yeah - most of Maryland is flat (eastern shore) or rolling (suburbs of Baltimore and DC) but western Maryland starting with Frederick heading out west is the foothills of the Appalachian Mountains (the trail runs about 15-20 miles west of Frederick).  The higher peaks are in West Virginia but we actually have ski resorts!! 

I did a sprint tri last weekend about 30 miles south of DC (16 mile bike leg) with 1400 ft of climbing.