I decided I'm going to hike/bike/run across Connecticut - and started this last weekend.
The New England Scenic Trail goes from the MA border down to the Long Island Sound in Guilford.
On Saturday did the Beseck Mountain segment (hiking boots/trekking sticks, etc.) and on Sunday did Bluff Head by Guilford. All have similar characteristics from north to south (volcanic eruption with westward facing basalt cliffs).
This evening did a trail run from Albany Ave (Reservoir 6 in West Hartford) to Heublein Tower on the Metacomet Trail. Tough when it starts to get dark around 6ish. Several trips but no problems.
Tough running on rocks/boulders/roots/etc. but I like the variety compared to running on asphalt.
If I had to run across a state, Connecticut would be near the top of the list. #1 might be Maryland, north to south. I toyed with the idea once on a visit.
Happy trails.
Speaking of MD, I really wanted to ride my bike from Harper's Ferry to DC (or vice versa), but I never got around to it.
Running from the Canadian border to the Pacific Ocean along the Alaskan Panhandle would be pretty short in some places as well. Plus: gravity would give assistance.