#RealTravel: I Quit My Job to Visit All 50 States In 365 Days

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Kelly sold everything she owned (except for the car you see here) to spend a year traveling to all 50 states (Photo: Kelly Will)

Who: Kelly Will, 34. After nine years as a celebrity gossip columnist in New York City, I sold everything I own to cross the United States for one year.

Why: There is only so much one woman can write about the Kardashians. I was losing it. I was tired of chasing the celebrity story. I would watch cable news and daydream about exploring the nation and getting out in the country to interview everyday people about their lives.

When: May 2013 – May 2014

Where: I traveled to all 50 States in 365 days. I stayed with a lot of strangers who are now my best friends. I didn’t watch any TV or read celebrity mags; I left my old career in the dust and dove into different adventures each day with new friends.

Kelly (second from right) makes friends in Cincinnati (Photo: Kelly Will)

Budget: I sold everything, all my posh evening gowns and Jimmy Choos, furniture and artwork. But I kept my Honda CR-V. I funded this on my own and lived on a TINY budget of $175/week. You can only drive so many miles on that, even in a Honda.

RELATED: 8 Tips on How to Quit Your Job and Travel the World

A Social Experiment: Two weeks before I arrived in a state, I sent out emails, Tweets and Facebook messages telling all of my friends and family where I was headed. They responded big-time with potential host homes.

Kelly takes the plunge at Wyoming’s Granite Hot Springs (Photo: Kelly Will)

Biggest Challenge: Driving on through the fear. With no income and no home, I felt on the edge every day. The only security I had was the immediate home I was in. The next host could back out — and often they did, and I would have to scramble to find a safe roof for the next stop. My mind produced a lot of stories to create a sense of terror and failure. Every morning I woke up to meditate and try to sweep the fear away. The mind game was and still is rough on me. It will always be my greatest challenge. Living in the moment is hard!

Quiet States: Finding hosts in Idaho, Montana and Wyoming was difficult. The week before I was set to depart for Idaho, I had no hosts in any of those states. I was desperate and I started asking for help from people I randomly met each day. But it all came together; just a day before I left for that part of the country, I managed to line up one host in each state. Better yet, by the time that part of my journey was over, I had stayed with three hosts in Montana and two in Wyoming. I remember those days often when I am panicked about something not working out.

Things got a little scary before Kelly’s trip to Idaho, but this view somehow made it all worth it. (Photo: Kelly Will)

A Memorable Moment: It was negative 20 degrees when I pulled up to a cabin in Maine in January. My host, Rod, wanted to take me ice fishing. I was happy to tag along. Rod, a lawyer by trade, looked questionably at my coat and gave me his extra gear, including his size 10 boots, so I could wear four pairs of socks inside them. He walked, I clomped out to the ice. Rod taught me to drill and scoop the hole while he did all the work that required taking his gloves off, like putting the minnow on the hook. Later that night, he had to Super Glue his fingertips to fix the splits and cracks on his hands from the frigid water.

Ice fishing with Rod in Maine (Photo: Kelly Will)

Why I Loved It: I became part of the families I stayed with. People made delicious meals and treated me like a kid home from college. I now feel like I have a friendly place to visit in every single state. I drove 36,000 miles, connected with over 600 people and stayed in 164 homes.

The writer (on left) in Key West, Florida with one of her many cross-country host families (Photo: Kelly Will)

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Hardest Day: The day I landed in Hawaii, my last state. At the peak of success, I was depressed. My supportive friends, family and host families were congratulating me and all I wanted to do was cry. Despite the daily discomfort and lack of security, I came to love being on the road and love the woman I was on the road. Everything I knew was over. My experiment was a success and I couldn’t enjoy it. I was blinded by a whole new set of fears when the wheels hit the tarmac in Hawaii. It took a few days to calm myself down and soak up The Aloha State.

Kelly’s last stop: Hawaii (Photo: Kelly Will)

What Have You Learned? Travel is the greatest education I have ever given myself. It has taught me that everyone has a great story to tell. One day during my journey, Betty, my host in Montana, was filling me in on her life. As she went from one story to the next, she suddenly recounted the time she met Ronald and Nancy Reagan in the White House Rose Garden! Today, I listen more. I stop and talk to people on the street daily.

Kelly tells her story to high school students in Iowa (Photo: Kelly Will)

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How I Changed: I understand how important people are in my life. I used to be much more of a loner. I am inspired by the human experience: listening, interacting and watching people live their daily lives.

Making new friends in Oregon (Photo: Kelly Will)

Favorite Spot: Guerneville, California

Why I Love it: Guerneville is deep in the heart of Sonoma wine country. From this one small town, you have easy access to the Russian River, Armstrong Redwoods State Natural Reserve, the Myacamas Mountains, many great wineries and the Pacific Ocean. In addition to the usual cocktailing and outdoor adventures, there are amazing restaurants and resorts in this tiny town.

Guerneville is a great place to enjoy Sonoma’s wine country (Photo: Kelly Will)

Overnight Stays: Boon Hotel + Spa offers a full retreat feeling just one mile from Armstrong Redwoods State Natural Reserve. Bonus: Boon is dog friendly. Borrow bikes, swim in the pool or settle in for a day of luxurious spa treatments.

Free Wine & Tours: The Korbel Champagne Cellar is just outside of downtown and has free tours around the estate and free sparkling wine tasting all day. Stop in for a break and walk through the gardens and dine at their café and deli loaded with incredible homemade salads, cakes, sandwiches and pizza.

Unique Shopping: Boho Lani is just around the corner on River Road in the heart of downtown. This chic shop and showroom’s name means Bohemian Heaven and it carries one-of-a-kind pieces made by female artisans from around the world.

Memorable Meals: Boon Hotel + Spa has two sister eateries on River Road. For lunch, pick up a sandwich at the chic Big Bottom Market and for supper try Boon Restaurant. I highly recommend Dick Blomster’s Korean Diner for out-of-this-world macaroni & cheese with kalbi, Kobe hot dogs, and fried peanut butter & jelly with ice cream and Pop Rocks.

Dick Blomster’s Korean Diner macaroni & cheese with kalbi (Photo: Kelly Will)

Bar Hopping: It is easy to pop in and out of the many local bars lining River Road (aka Highway 116). An eclectic mix of townsfolk and tourists happily join in evenings together with karaoke at the local pub, sing-alongs at the piano bar and dancing at the discothèque. There is a little something for everyone in this town, even a quiet bar with a calmer atmosphere for those looking for a peaceful nightcap.

Favorite Spot: Portland, Oregon

Its relaxed, friendly vibe made Portland one of Kelly’s favorite stops (Photo: Kelly Will)

Why I Love it: People are relaxed, kind and even quiet, but there is also a sense of community and concern for the environment. Portland is a friendly city with endless options for food, beer, wine and great ciders. It’s apple country!

What I Don’t Love: Portland is a tad rainy. But the thing about Portlandia is that people commit to being outdoors in rain or shine— as long as you have a great raincoat, of course.

Must Stop For Doughnuts: Everyone has heard of the Maple Bacon Glazed Doughnut by Voodoo Doughnut by now! This hip, pink destination is a must and though the line looks long, it moves fast. Don’t worry about boutique doughnut prices; these confections will fit any budget, starting under $1!

Voodoo Doughnut (Photo by Kelly Will)

Best Eats: The food truck revolution has taken over Portland dining with more than 500 total within the city. Visitors will find a smattering of them in every neighborhood. They are so popular, they have a food truck website that maps the locations of each truck.

Must Hike: Multnomah Falls in the Columbia River Gorge is a destination for everyone who visits Portland. There are paths, trails and hikes for all skill levels.

You haven’t seen all there is to see in Portland until you’ve stopped by Multnomah Falls (Photo: Kelly Will)

Lush Gardens: Portland is home to some of the most beautiful gardens in the country. The International Rose Test Garden is free of charge and sits at the foot of the parking lots to the Portland Japanese Gardens, where admission is $9.50/adult.

What’s Next: I love this country and I want to keep traveling and meeting people. I am also writing a book about my pre- and post- celebrity adventures. Read more and stay connected with me on my website.

Parting Thoughts: Life is short, so make your life experience beautiful. Smile a lot, live in the moment and connect with people. One person can change your life.

These friendly hikers in Lake Tahoe, CA are among the many friends Kelly made on the road.

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