Join Date: Dec 2005
Location: Reisterstown, MD
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I haven't dont all of that, but I have biked and driven a fair amount of roads along the way.
My recommendations. First off 26 is NOT that fun in certain spots. It is bikeable, but as it takes you a bit out of your way I wouldn't bother.
I would probably consider RT 144 over 40. 40 is tons of strip malls, no good shoulder and overall probably not that much fun. I have biked 144 from downtown Ellicott City west. It is part of my commute to/from work. The only semi annoying part is a section where 144 merges onto Rt 40. It is pretty short (maybe .5 mile) and what I do is take the far left turn lane. When I get on Rt 40 I actually ride on the "shoulder" section between the left lane and the grass median between the roads. That sets me up for the left turn lane to get back over to 144.
From there you can probably take 144 for a good bit. I don't mind it at all.
Here is my likely route
Keep in mind I haven't biked all of those roads, but there are plenty of other smaller roads that could be substituted.
Looks like a really fun ride. I did something similar last summer. My wife and I had a party on a saturday night. So I dropped the kids off at my parents and biked home taking this route
Then the next morning I biked back down to pick them up. It was pretty awesome, mostly the feeling of not just riding, but getting somewhere that was a decent distance away.