When Jeffery Kennedy decided he’d hop on his bicycle to raise money for charity, he had more than a trip around the block in mind. His idea included almost 6,000 miles, 16 states and provinces and 75 days on the road. With just his bike, his gear and the throngs of well-wishers who will be following his journey via the internet, Jeffery’s adventure begins May 30, 2009.

Jeffery is using his Anchorage to Key West cycling trip to raise money for One Heartland, a national organization dedicated to greatly improving the lives of children impacted by HIV/AIDs. I asked Jeffery to take a break from his pre-trip schedule to talk to Wandering Educators about his expedition.

Where’d the inspiration come for this trip?

It began 8 years ago when I took a map of North America and started to look at all of the places I have been. The places that really stood out were along the Rockies. My father and I took many long distance driving trips when I was young to the western frontier. I love the west! So, I decided for the first half of the ride, I will stay in the mountains from Alaska to Colorado. I also love the Great Plains, the Ozarks, The Smokey Mountains, the sea coast of Georgia and Florida.

Tell us about camp One Heartland? How’d you get connected with them?

One Heartland is a camp for children and teenagers impacted by HIV/AIDS. It gives these children a chance to meet others like themselves. It helps them find strength in themselves and in each other. I was invited to a Party with Heart fundraiser with a mutual friend. That day I met the founder and CEO Neil Willenson. I told him my idea.  The rest is history!!

How did you select your route? Any special stops along the way?

The route took months of research. I went through 12 drafts of the route before the final route was made 3 months ago. I wish Google Streetview was made earlier; it would've been easier looking for wider shoulders on state highways. I will be traveling through some of the most beautiful wilderness in North America. I will be riding through the Alaska mountain range, Canadian Rockies, Jasper and Banff National Parks, Grand Tetons, Colorado Rockies, Hoosier Pass 11,500 feet, The Great Plains of Kansas, Ozarks of southern Missouri, Smokey Mountains and the sea coast of the Atlantic.

What kind of gear will you be traveling with?

I will pulling a trailer carrying about 60-70 lbs of gear.  Some bicycle spare parts, tubes, tires, tent, sleeping bag, about 2 gallons of water and Powerade, 3-5 lbs of food, rain gear, wind breaker, clothes, bathroom amenities, etc.

Have you given your bike a name?

I have alway been a fan of the Space Shuttle. LOL.  I can't say I’ve given a name to anything, but if I had too, I would probably call the bike "Endeavor,” after the space shuttle Endeavor. This trip is a huge journey.

This is your first solo cross-country trip, how does your preparation differ from previous group trips?

First on bike tours with touring company, everything is done for you. Hotels, food and camping arrangements are all ready for you when the riding day is over. Basically you just ride! These companies are very nice. It makes the rides very enjoyable. It also gives you the chance to meet and greet with other riders on the trek. I have met some great people along the treks I have done in the past.

Now for this trip, I'm all by myself.  I have to do everything for myself.  Mentally it will be harder. No one to lift my spirits up during a rough day.

Who or what will you rely on for support during those emotionally challenging spots of the trip?

I hope that inspirational words from my supporters will get me through. I also think that great weather will help boost my mood in the great wilderness of the north.

What special plans have you had to make to be prepared for an emergency?

I do have the SPOT Messenger emergency beacon.  I can pinpoint my location via GPS to the nearest emergency center. 

Any part of the trip you are particularly looking forward to?

I think the best part of the trip will be the Canadian Rockies. Jasper and Banff National Parks. I was there when I was 8 with my father. To this day, I still remember the detail of the beauty of the wilderness of rugged mountains, glaciers, glacier fed rivers and lakes, and the wildlife. If heaven exist, I hope its there.

Any part of the trip that your are anxious or nervous about?

I am more nervous about isolation. I'm a social butterfly. I love people. How will I handle being alone? That we will have to wait and see. Another big worry is TRAFFIC. There are some scary drivers out there.

Corey Taratuta/IrishFireside is the Ireland Editor for Wandering Educators