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Quite a few times. The most enjoyable trip was the one where I took my time, stayed off the interstates as much as possible, had meals at the little mom and pop shops, and stopped when ever I saw something the may be interesting.
Make a playlist for each state you plan on going through. Get Kerouac's "On the road" as an audiobook.
We did this too kind of, usually find music from an artist from that state, like Gretchen Wilson in Illinois, Sara Evans in Missouri, Carrie Underwood in Oklahoma, Rascal Flatts in Ohio etc. Also listen to the local radio and see how it changes, especially with the Spanish stations in California and New Mexico.
About the east-west divide, on the I-70 route I'd say the first truly western city to me was Colorado Springs, though parts of western Kansas and eastern Colorado have a semi-western feel. I didn't think Kansas City felt particularly "western". Along I-40, I think the divide is somewhere around Oklahoma City or eastern Oklahoma, as Arkansas is clearly a Southern state.
Have you ever done a road trip across the country? What was the primary interstate highway that got you across, or what interstate were you on when going across the Rockies? (I-90, I-80, I-70, I-40, I-10). What did you see along the way? What were your favorite stopovers? Did you have fun? Would you do it again?
Took I-95, I-10, I-80, and many others.
Drove down the East coast from New Jersey to Florida, across the bottom of the country through the South, the Southwest, to California. Up the West coast to Washington, and then back across the Upper Rocky Mountain West, Plains, and Midwest.
Stopped in:
Charlottesville, VA
Richmond, VA
Asheville, NC
Mt. Airy, NC
Winston-Salem, NC
Buxton, NC
Charleston, SC
Beaufort, SC
Savannah, GA
St. Augustine, FL
Pensacola, FL
Mobile, AL
Dauphin Island, AL
Vicksburg, MS
Natchez, MS
St. Francisville, LA
Jefferson, TX
Fort Worth, TX
San Antonio, TX
Fort Sumner, NM
Santa Fe, NM
Taos, NM
Albuquerque, NM
Roswell, NM
Carlsbad Caverns National Park
Tombstone, AZ
Tucson, AZ
Sedona, AZ
Grand Canyon National Park
St. George, UT
Zion National Park
Las Vegas, NV
San Diego/Coronado, CA
Anaheim, CA
Burbank/Los Angeles/Hollywood/Venice Beach, CA
Santa Barbara, CA
Carmel, CA
San Simeon, CA
San Francisco, CA
Crater Lake National Park
Tillamook, OR
Portland, OR
Mt. St. Helens in WA
Leavenworth, WA
Seattle, WA
Coeur d'Alene, ID
Kalispell, MT
Glacier National Park
Yellowstone National Park
Jackson Hole, WY
Cody, WY
Shell, WY
Deadwood, SD
Keystone, SD
Madison, WI
Chicago, IL
Pittsburgh, PA
Took just a little over a month.
My favorites? The national parks - especially Glacier and the Grand Canyon, and the great cities of Savannah, Charleston, and Portland.
I made a cross country trip several years ago and it was a really cool experience. I met up with friends in several places and some of the places I was on my own.
I started on the East Coast and on the way out West I took a southerly route through Tennessee, Arkansas, Texas, New Mexico and Arizona to arrive in Southern California. I then went up the Pacific Coast Highway and came back through Nevada, Utah, Colorado, Kansas and Missouri. Sometimes I took the highway and sometimes I took smaller roads. I had a pretty loose time-table for most of the trip so if something caught my eye I would stop and check it out.
My favorite natural places were Bryce Canyon, Yosemite and Arches National Parks. My favorite cities were Las Vegas, San Diego and San Francisco. But there was interesting stuff almost everywhere. Big cities, small towns and the country all have a lot to offer. I saw a lot of the country I had never seen before and I would encourage anyone to take a trip like that if they have the chance.
From Raleigh, NC to SoCal. Was not the driver and paid no attention to the highways, but it's a beautiful drive from Raleigh until you get through eastern Oklahoma. Downhill from there; nothing but dirt and cacti until you get to CA. We barely stopped. Also drove from Kansas City to Tampa. That was a spectacular trip, just beautiful -- but again, we barely stopped.
I'd do it again, but in our motorhome instead of the car, and on all the scenic routes.
When I was 13 in 1974, we drove across half the country. We went from Cincinnati where we lived to Denver to visit my uncle (my mom's brother) and his family. There were seven of us in Mom's station wagon--she and my aunt, my two sisters and me, and two cousins. AM radio, no air conditioning. You try doing that today and all of your passengers would die!
We stayed in Denver for a week, then drove north to Yellowstone, then east to Mt. Rushmore, and back to Ohio.
The next summer all of us except for one of my cousins went in the same station wagon from Cincinnati to Orlando and back.
Went cross-country six times. Drove I-10, I-40/Rt 66, I-70 and I-80. Some day I'd like to take Route 50 (local) all the way across. Need more time for that. Yes, I do plan on driving cross country again. Also have taken I-95 up and down the east coast.
Cross country trip #1 jacksonville florida to frenchville maine(95 to highway 1 in maine). Cross country trip #2 boston mass. to Bremerton wa. taking 95 to I think 80 then to 90 pretty much the rest of the way with a few highways to bremerton. Trips #3,4,5,&6 bremerton wa to chino hills ca using 5 almost the whole way. I love how i have been blessed with the opportunities to take these trips oh and two other trips from atlanta georgia to toms river new jersey. Sorry for grammar and punctuation posted on my phone.
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