Any idea on interesting stops along the way and how long this will take?
It's freeway after Glasgow, so five hours or a bit less should do it. The Lake District is about at the midpoint -- it's not my favorite area, but most people really like it -- you should go see for yourself. If you swing in, my odd slelf does like the pencil museum and the museum of marine steam engines.
We have visited lots of interesting places in southern Scotland and northern England. You might enjoy the borders area of Scotland, especially Melrose and Dryburgh Abbey.
Northumberland is full of castles. Hadrian's Wall (check out the area around Once Brewed and Housesteads Fort)is also between Loch Lomond and York. The Yorkshire Dales are beautiful and full of more abbeys and castles. Fountains Abbey is outstanding.
Get the Michelin orange regional maps for Scotland and northern England, highlight the sights, and then decide on the logical order for visiting them. I would skip the Lakes district in favor of the more eastern part of northern England.
For distances and times, check out theaa.com We find their figures to be quite accurate.
Durham is an hour or so north of York. Definitely worth a stop for its scenic cathedral. Hadrian's Wall is another worthwhile stop if you can find it.
Wanlockhead, worth a call
Hartside Cafe, Tan Hill Inn,and Killhope Lead Mine, High Force would make a more intesting route than the A66
If I were driving from from Loch Lomond to York, I would take a couple of days at least and explore the Borders. I would visit at least one of the Abbey's and then I would spend some time at Hadrian's Wall. I would want to explore the forts and do at least a short walk along the wall. A visit to Hexham would give some perspective on the Border area when the raids across the Borders were strongest. I would stop off at Durham and visit the Cathedral and the town. I also might revisit the Saxon church in Escomb, http://www.escombsaxonchurch.com/ Rivaulx Abbey is also amazing and on the way to York.
Pam
I haven't taken your exact route. Hadrian's wall and maybe an Abbey ruin would be stops I would look for.