Round America Trip – Rules of the Road

The trip ‘Round America covered 50 states and over 2,500 towns. We wanted to make the trip special, and we established Rules of the Road.

These are the Rules of the Road:

Rule #1 See the real world.  Stay off the interstate highways.
Rule #2 Eat pie.  Eat where the locals eat.  Avoid franchised restaurants.  “Slow food” rather than fast food.
Rule #3 See the sights that others miss.  Don’t visit many theme parks.
Rule #4 Plan to enjoy the unexpected.  When something catches your eye, check it out.
Rule #5 Try new things — new places, new people, new food, new experiences.
Rule #6 Stop and smell the roses…or whatever.  No need to rush; enjoy the journey.
Rule #7 Think local.  Listen to local radio stations; read local papers; and watch local TV.
Rule #8 Make the best of every situation,  If it seems boring or ugly or wrong, look again.
Rule #9 Be smart.  Be safe.  Be prepared.  Exercise every day.  Keep the gas tank full.
Rule #10 Preserve the experience.  Maintain a journal; keep records; and take a lot of photos.

Round America Trip – The Travelers

Bill Windsor

Bill Windsor; age 54; brother of three; husband of one; father of two; grandfather of one; serial entrepreneur –has started 44 businesses in the last 33 years; publisher for much of his career; author of numerous magazine articles and business publications; record collector with one of the world’s largest collections of 45-rpm records; owner of 1955 Chevrolet Police Car; likes doing things that others might never think to do.

Barbara Windsor

Barbara Windsor; much younger than Bill; sister of three; wife of one; mother of two; grandmother of three; has worked with Bill in many of his businesses over the last 33 years; great interior decorator; doll collector; can’t even believe the crazy stuff Bill comes up with; hesitant about the trip “Round America at first, but became enthusiastic once she got to fly home a few times to see Brittany and Miss Madison.

Round America Trip Scorecard

The trip ‘Round America covered 50 states and over 2,500 towns.
This is the Trip Scorecard — tracking important statistics throughout the trip.

Category Planned Actual
Duration 100 days 148 days
Mileage 19,631 29,450
Countries Visited 3 3
States Visited 50 + DC 50 + DC
Cities Visited 2,538 over 2,500
People Met 1,000 over 2,000
Attractions Seen 1,000 need to tally
Photos Taken 5,000 14,341
Meals Eaten 300 need to tally
Pies Eaten 100 177
Antacids Consumed 150 45
Gallons of Gas 1,309 1,733
Flat Tires 1 1
New Tires 4 9*
Oil Changes 7 6
Speeding Tickets 0 1 — disputed
Cars Passed 0 33
Times Lost 0 many
Chapters Written 51 ?
Enjoyment Massive Massive

* One tire was for friends in need.

Round America Trip Overview

On April 1, my wife and I left on a long-anticipated trip that we have affectionately referred to for several years as “The Pie Trip.”  The trip covered all 50 states, over 2,500 towns, and over 29,000 miles.  The trip ended on August 26.  We wrote about the trip each night in our Daily Journal.

The idea for this trip originated in 2000.  I proposed to Barbara that we go on “The Pie Trip” — just take off and travel the country and “eat pie.”  We would go on the backroads and eat in cafes and diners where the locals eat (where they always have pie) and just learn about the places we go and the people we meet.  We would write a book about the experience.

We became busy with other things, and the trip was postponed.  I was more than a little disappointed when I discovered a book titled American Pie published in 2002 that had a strikingly similar concept and a great name.

But the idea for the trip was bolstered by my experience driving a 1955 Chevy Police Car from Dallas to Atlanta and on to Orlando.  I spotted the car on eBay, and I was the winning bidder.  The seller, Steve Jobe of Southlake, Texas, told me that I would be missing out if I had an auto transporter ship the police car from Dallas to Atlanta.  He convinced me to drive the car, and I did.  People everywhere smiled, pointed, and waved.  I got literally hundreds upon hundreds of thumbs up and honks as I drove down the highway.  One lady even took a picture at 60 miles-an-hour as we drove side-by-side down the Interstate in Louisiana.  In Ruston, Louisiana, two police officers pulled me over.  I knew I wasn’t speeding.  They smiled and offered to trade cars.  I always drew a crowd at every gas station and fast food stop; many people took pictures.  I had the opportunity to talk with hundreds of people who I would have never met.  And best of all, I saw THOUSANDS of smiles from people passing by.  It was such a happy experience that I felt we had to get serious about planning the trip.

We wanted to do something unique, so we decided to visit all 50 states in one trip.  Barbara vetoed making the trip in the 55 Chevy Police Car.  I knew we would meet tens of thousands of people in that car, but the risk of a breakdown on remote two-lane roads was too great.  Visiting all 50 states in one trip was to be unique enough!

The new plan was to go entirely around the country with a well-planned route.  We would visit all 50 states.  I mapped an itinerary that took us from Atlanta to Savannah to Daytona Beach to Miami to Key West to New Orleans to Brownsville to Tucson to San Diego to Los Angeles to Flagstaff to Santa Fe to St. Louis to Nashville to Atlanta to Louisville to Des Moines, to Denver to Salt Lake City to Las Vegas to Los Angeles to San Francisco to Seattle to Anchorage to Minot to Duluth to Mackinac Island to Toledo to Cleveland to Buffalo to Burlington to Fort Kent Maine to Calais to Providence to New York to Washington DC to Norfolk to Myrtle Beach to Charleston to Savannah to Atlanta and all spots in between.  Last stop was Hawaii to complete our trip Round American.  If you look at a map, you’ll see that we essentially outlined the USA and then completed one circle through the non-border states.  We visited all 50 states and passed through at least 2,500 towns.  We logged over 29,000 miles by car.

We saw major sights, including Mount Rushmore, Alcatraz, Niagara Falls, and Hollywood, but we also saw other attractions such as the world’s largest ball of twine, the smallest church in America, the Forrest Gump bus bench, a house built entirely out of one log, the spinach capital of the world, the Roswell UFO Museum, the underground missile silos in North Dakota, the Judy Garland Museum, the James Dean Memorial, the Ben & Jerry’s factory, and assorted roadside attractions.  We made special detours to visit some highly-regarded pie places.

We tried to eat where the locals ate…unless the locals ate at franchised restaurants…as we sought to concentrate on good, independent local places and “slow food.”  Nothing too fancy; diners and cafes were our #1 choice.  We tracked each restaurant we visited and the roadfood we ate, and we have preserved that for posterity on our Road Food page.

A few people have asked what prompted the trip.  We wanted to relax, enjoy life, and see more of the USA.  We miss the kinder and gentler days of our youth.  Our parents took us on wonderful driving vacations as children, and we both miss that.  Most of our vacations with our children were airplane trips rather than car trips, and when we did drive, we drove on the interstates.

You don’t see much of anything on the interstates, so the decision to drive primarily on two-lane roads was essential for us to see and experience what was important to us.  We’ve been to most of the big cities, so we concentrated on smaller towns and areas where we’ve never been.  We saw the trip as a real celebration of the many wonderful things that our great country has to offer.  We looked forward to seeing and photographing patriotic displays that we saw along the way.

We were at a point in our lives where we could devote several months to take a trip of this magnitude, so the timing was right.  I always enjoy doing things that others haven’t done, so traveling to all 50 states in one trip would be a very satisfying accomplishment.  And, we hope our book will encourage others to truly SEE the USA!

We wanted a memorable experience.  We wanted to do something unique.  And we did!

We carefully planned the trip.  We established these Rules of the Road.

We are writing books about our experiences.  We are writing about “the places we go, the sights we see, the people we meet, and the pie we eat.”

A family tradition has been to end our vacations by creating a list of the best and worst of the trip.  Best meal, worst meal, best city, worst city, best excuse, worst expenditure — some serious and some funny.  As we approached the trip, we compiled a master list of bests and worsts to consider as we traveled, and we ended our trip by naming our bests and worsts.

We wrote daily, and we have provided a daily account and photos on the web site.  We tracked our experiences with a Scorecard as well — tracking various and sundry “vital statistics.”

As we take future trips, we will continue to add information and photos.  We hope you will check in on us occasionally by visiting the web site —

Bill Windsor