Organized from easier to harder.

Ride Notes Distance
Multnomah Falls Portland, OR. Hilly. 40ish miles
Denver → Golden 40ish miles on bike paths 40ish miles
Around Lake Tahoe Moderately hilly at elevation; snow possible 76 miles
Chicago ↔ Wisconsin With a hotel overnight 120 miles
Gravel bike touring in Montana Self-supported camping loop from Whitefish, with two days on a section of the GDMBR 4 days, ~30 miles/day
Mountain bike camping across Southern Utah Six-day guided and supported trip with a truck carrying water ~220 miles, 20,000’
BikeMaine (DownEast edition) Supported bike camping tour, a different route every year (my favorite may be the DownEast) ~400 miles over a week
Washington DC → Pittsburgh Almost completely off-road on the C&O Canal towpath and GAP rails-to-trails conversion 7 nights self-supported, ~350 miles
RAGBRAI Supported bike camping across Iowa with 10,000+ other people ~460 miles
Iowa and SW Wisconsin Supported Iowa bike camping, then self-supported from the Mississippi to Madison ~600 miles