Riding towards Sofia was very cold with a few more mountain passes, but the elevation was indeed getting easier and I knew that after Sofia it would be generally downhill towards Istanbul so I could feel a light at the end of the tunnel. At very the top of the last climb towards Kyustendil I was very cold and stopped in at a restaurant to warm up. The owner approached me and we talked about how there are a lot of cyclists in the area that like to race up the pass I just went up. He gave me free coffee and cookies and then showed off his biceps. He was a very proud 60 year old and I loved to see it.
The next day I made it into Sofia where I planned to stay for a few days over New Years. For some reason I thought I’d find something fun to do there, but I just wound up laying in my hotel room doing nothing. I’m at that age where I remember at some point I used to party on New Years but now all those parties are collapsed into a single memory that I can’t really remember many details of.
Anyway it was cool to ride around Sofia and explore their old buildings and big city parks. They had a classy lightrail system and most memorably, a STARBUCKS with FILTER COFFEE.
After New Years I headed south to Plovdiv. The terrain was flattening out and I was feeling like taking the smoothest route I could so I stayed on the freeway for a long time. It was great while it lasted. After a few hours a police car pulled me over and said, “bicycle, problem.” I told him, “Oh, OK!” and exited. I really feel like a freeway with a 10-15′ shoulder with faster cars is more a lot safer than a bumpy local road with no shoulder and endless cars overtaking me with less than a foot of buffer. It’s definitely more stressful to be off the freeway.
Eventually I did make it into Plovdiv. My expectations were very low, but Rick Steves suggested it on a video I saw so it feels like the right place to stop. And it was. There was a very lively old town that was easy to walk around on. The city felt small in size but lively like a big city would.
Bulgarian style 
My charming hostel 
Roman theater from 100 AD overlooking Plovdiv
I took a walking tour of Plovdiv and really loved it. I wished I had done more tours up to that point but so it was. There were only 3 visitors on the tour, me and a couple from Sofia: Ivan and Malvina. After the tour, we wound up at the same nearby restaurant for lunch where we fed the local cats and became fast travel friends.
The cats of Plovdiv 
Malvina and Ivan
They took me out to eat that night as well and showed me some delicious Bulgarian cuisine.
Sunset from atop a hill in Plovdiv 
hipster area of Plovdiv
I was sad saying goodbye to them knowing that they would probably be my last new travel friends of this tour.