I'd just watch the weather for 2,000 miles around, go where it's best for riding, stay on the back roads all the way. Eat at the mom'n pop cafe's, no chains, check out the local attractions.

 

From Atlanta
Up thru Nc-WV-Ohio-UP of Michigan-Canada over to Middle of US back down catching Mo & Ark

 

floppy weather still in mid May. If you are trying to avoid cold and wet

What about Big Bend? N'awlins and Galveston on the way. If you want some rockies, Carlsbad, Ruidoso. If weather not cooperating, tons of good roads west of San Antone, Leaky, Kerrville, Bandera, hill country. From there either north to western OK or over and up through east TX. The eastern part of OK has been mentioned. There and Arkansas could easy use a week....or more.

wandering across Tennessee is nice. Or Vicksburg Mississippi if you like history.

We still see wet fronts this time of year, but should be good temps in AR.

 

Eastern OK is beautiful. And Arkansas is a hidden gem that is often never thought about. And you literally could ride the backroads in Tennessee for all three weeks and not see the same city twice.

 

I'm loving these responses. Like many of you I'm former military -- 21 years in the USAF. My stateside assignments included MS, AZ, TX, SC, and OK but I always had a crotch rocket that made any significant touring impractical. Figures I'd move to ATL and THEN get the HD . I personally love the west but gotta follow the work.

Due to an alignment of the planets I've got 35 days off, but I promised the family a 2 week vacation together. Kids are growing up, I can't justify spending 5 weeks alone when in a couple years they will be off into the world. I'm about evenly split between hauling *** to UT or CO with the bike on a trailer or just keeping it east coast. I guess I'll have to see what friends are available for visits and what the WX holds and make a decision as the date draws closer. By all means keep the suggestions pouring in, this will be a great repository of ideas for shorter trips as time is available.

 

I'm in agreement with those who recommend staying south/southwest.
Less chance of a rain and warmer temps.
The Utah Canyonlands is some of the best riding and scenery that you'll ever see especially in the May time frame you have and you can always head north until the weather convinces you differently.

New England, Nova Scotia and NL are summertime destinations unless you're going by car as it can get quite cold, windy and wet up that way.

I'm in Michigan and the only direction that I'd consider riding towards for any distance in May would be south.

 

I am in a similar situation. I am taking off 4 weeks and planing to ride from Fort Lauderdale to Vegas..then back through Rushmore ,Sturgis etc. I would love to experience riding through the monument Valley and all of that at night. But I hear it's a dangerous run at night due to the night life and visibility. Any locals can you advise me on that.

 

Night Rides have been some of my greatest pleasures - and some of my greatest risks - in riding. Yes, there is enhanced risk riding at night. In 2014 I stayed a month camping in DeMott Meadow National Forest Campground just North of the North Rim Grand Canyon National Park. In that 30 days 3 cagers took out 3 buffalo at night while I was there. Or, you could say 3 buffalo took out 3 cagers ... anyway, nobody won. Large black animal on black asphalt on a dark night very hard to miss. I have to be very careful NOT to overdrive my head light and not to let the glare from oncoming traffic blind me. I reduce my speed, frequently to below the speed limit in hazardous areas, and pull off the road for tailgaters and heavy streams of oncoming traffic. Coming out of the North Rim Park one night I sounded my horn before each curve to alert the all to common Mule Deer of my approach. I try to avoid night rides on roads too narrow or with no shoulder to pull off on. I carry a one man tent, thermarest mattress, and Good sleeping bag to be able to bivouac overnight if necessary. If there is not a Forest Service or BLM camp ground immediately available, most National Parks are surrounded by either National Forest or BLM land where "Dispersed Camping" is allowed along fire roads, so I have never been forced to bivouac right next to a major highway. Some of these dark, cold, lonely camps have been rewarded with some of the most amazing sunsets, moon rises, and glorious night skies you could ever imagine. And if you want to add a little adrenaline to your life, let a pack of coyotes open up 25 yards from your tent at midnight just as you are falling asleep. Bill Staines knows about something similar.

 

I could do 3 weeks in the Med. One week in Italy, one in France and one in Spain.

 

Out here, Ut CO WY MT many Mt. passes don't open till Memorial Day. Spring run off will be at a peak so river rafting would be a blast.