My 30 Best Road Trips

Easy as it would be to rage on with a post about the union-busting at home or the latest foolish U.S. military adventure, I choose to keep it light-hearted with a post profiling a list of favorites from my three decades of Midwestern road trips. Road trip season for me traditionally starts this time of year so it's a good time to look back to the classics. I was originally considering a top-20 list, then expanded it to a top-25, but realized I needed a top-30 list to do service to the best of the best of the 180 I've cataloged going back to 1990. Road trip season for me traditionally starts this time of year so it's a good time to look back to the classics.

#30. St. Peter/New Ulm 2007--I had a lot going on during my vacation week in August 2007, going to the county fair every night as well as doing a video of my hometown with a buddy and going out on a date with an old classmate. Good spirits abounded and with the help of perfect summer weather, made for a fun little five-hour getaway which always accentuates this trip, a retread of the towns I visited with my dad doing vinyl repair work at car lots in the summer of 1990. To this day, I get a thrill out of driving into the scenic town of New Ulm. And there's something that still gets me about going through population center Mankato as well.

#29. New Year's Eve 2001--Every year in the week between Christmas and New Year's I select a different destination, usually in scenic southeastern Minnesota, for a road trip. This year, I got to intensively explore Winona County for this time. Road trip fever hit its peak for me in 2001 as I made official my quest to visit all of Minnesota's 734 communities and went out of my way to score new ones, and this trip allowed me to score 17 new towns, and some very scenic ones at that including Elba and Stockton. It was a sunny but blustery winter day, perfect for this kind of trip, and on the way home I discovered a country station out of Rochester playing some songs I hadn't heard in years that kept things interesting on the slog home around dusk.
Defining songs: Aaron Tippin "Whole Lotta Love on the Line", David Lee Murphy "All Lit Up in Love"

#28. La Crosse 1990--At various points in the past, my parents would head out to La Crosse, Wisconsin, to see the fall colors in the Mississippi River Valley at their peak in October, but this was the first year it really stuck with me and became a tradition. I was 13 years old and after the previous summer had just gotten my first taste of road trip fever. I had remember some of these impressively scenic southeastern Minnesota towns from the past and loved revisiting them, particularly Lanesboro, Houston, and my favorite, Rushford. High points included driving up to the scenic overlook over Rushford, eating at Arby's in La Crosse back when Arby's was an exotic treat, and driving home through some previously unexplored little towns in northeastern Freeborn County including Oakland, Moscow, and Lerdal.

#27. Northern Minnesota 2009--Early last decade, I made a September tradition of exploring various areas of northern Minnesota, originally with the express purpose of getting to obscure little towns and help my cause of getting to all 734 Minnesota towns. I completed that expedition in 2007, but continued to head northward because I discovered it's a really nice time of year to be up there. Normally, these northern Minnesota trips send me to the woods of northeastern Minnesota, but on this trip most of my exploration was the Red River Valley in the Fargo-Moorhead area of northwestern Minnesota. I had been to this area several times before, but never during their fall sugar beet harvest. The back roads in Clay and Norman Counties were littered with sugar beets that fell off the truck and looked like dead armadillos on the highway. With perfect late summer weather as a backdrop to my thorough exploration of Clay and Norman Counties, I discovered that it's as nice to be in northwestern Minnesota in mid-September than it is in northeastern Minnesota.

#26. Minnesota River Valley 2000--During spring break in college, my dad was always another few weeks away from being called back to the railroad and I conned him into making journeys to western Minnesota. This was the last year of college and the third trip I made with him in last March. It was a gloomy day, but it was still a hoot visiting a flurry of new towns in west-central Minnesota, including Granite Falls, Montevideo, Appleton, Benson, and Willmar, among many others. Nothing electric happened on the trip, but I scored 24 new towns and got to see the geese migration along Lac qui Parle in western Minnesota for the first time. Great memories.

#25. Sioux Falls 2002--The Sioux Falls trip is the granddaddy of them all regarding my road trips, another throwback to the vinyl car lot repair summer of 1990 with my dad. The 2002 trip was significant because I had just begun a job at the newspaper and realized my schedule was gonna be more crowded and needed to bump up the Sioux Falls trip from its long-standing timeframe in late July to June, in this case mid-June, the first weekend I had free in several weeks. To my surprise, I found the trip more fun in June than in July, with the corn crop still barely peeking above the ground and giving me a much better vantage point than what I was used to in July. On top of that, it was a nice steamy summer day which I always prefer for this trip and everything just sort of clicked. I had a good feeling in the early weeks of 2002, preparing for long-distance girlfriend Dana's promised visit to my hacienda, and that undoubtedly raised my spirits for this road trip even though that wouldn't have a happy ending.
Defining music: Phil Vassar "American Child" playing on the radio as I was in the Arby's drive-thru in Sioux Falls.

#24. Trans-Freeborn County 1999--Normally I make my journey through most of the small towns of my home county the day after Thanksgiving, but in 1999, I had to spend the weekend working on a huge paper for my senior year of college and my dad, who usually came along back then, was busy roofing the barn. When I returned home for Christmas break, I found both parents were home in bed with the flu, and I figured the next day was a good opportunity to take to the road for a belated Freeborn County adventure. It was a bitter day, well below zero, and my Ford Fairmont had gas-line freeze-up and wouldn't start, leaving me navigating my mom's car on what was effectively my first solo road trip. Most people don't like doing things alone, but I always have and I found this solo safari to be inspiring, listening to music as I drove and experiencing the towns at my own pace. Turned out to be my best Freeborn County road trip experience since the original.
Defining music: Randy Travis "A Man Ain't Made of Stone"

#23. St. Peter/New Ulm 2001--I was out of work the entire year of 2001 and most obsessed with road tripping and picking up new territory. It was also the year that nearly all of my road trips were solo runs, as opposed to the years earlier where I usually went with my dad. The extra freedom was beneficial in setting my own terms for the exploration and in hitting some backroads through unexplored townships in south-central Minnesota. This is always a fun little half-day joy ride, usually in early August, but the "new frontier" aspect of this particular year's journey made it my favorite St. Peter-New Ulm trip.
Defining music: Jeff Carson "Real Life"

#22. New Year's Eve 1999--Here was a road trip literally on the dawn of the new millennium...on December 31, 1999. It was a beautiful sunny day in an unusually warm winter without a trace of snow on the ground as my dad and I safaried to northwestern Iowa, visiting the Okoboji area for the first time in my life, as well as towns like Estherville, Emmetsburg, Algona, and Buffalo Center. It was a nice change of pace and I had some good mojo about the Y2K event only hours away, and the delicious as always chicken and swiss sandwich from Hardee's in Estherville was frosting on the cake. I haven't been back to the area since but plan to return this coming New Year's Eve.

#21. La Crosse 1995--The family generally travels the same route every October to see the fall colors of southeastern Minnesota, which is understandable given the unparalleled scenery of this particular route. But this was the year that everything seemed to be perfect, most specifically the 75-degree weather that allowed short-sleeved exploration of the scenic overlook at Rushford, of which we explored additional trails with an even better vantage point of the town that year. This was at the beginning of my senior year of high school and I was increasingly glum about the major change in my life that lie ahead. This was a nice old-fashioned getaway to more relaxed times.

#20. Minnesota River Valley 2005--I had just been let go from my newspaper job in March 2005 but stuck around my apartment until the end of April before moving back in with the parents for a few months. One excursion that I enjoyed during that time was an April road trip across the Minnesota River Valley in western Minnesota on a Friday before heading home to the parents place for the weekend. This would be the sixth and final Minnesota River Valley road trip but I retired it in style on a perfect spring day with a sense of freedom and new beginnings on the horizon now that I was done with the newspaper while exploring the back roads of Kandiyohi and McLeod Counties, among other places.
Defining music: Def Leppard "Pour Some Sugar on Me" (which I got a kick out of blasting from my car radio while driving through the uber-religious Dutch town of Prinsburg); Dan Seals "Bop", Ronnie Milsap "Stranger in My House"

#19. New Year's Eve 1998--My New Year's Eve trip tradition started in 1995 and every year the destination was someplace different. This year would be my first journey to the Wabasha area in southeastern Minnesota. I had heard good things about the area, but ended up more impressed even than expected. The area's bluffs took on an interesting dynamic in the dead of winter with frozen water runoff on the edges of the bluffs looking like an ice waterfall. It was also my first experience with seeing the thousands of bald eagles that flourish in the area over the wintertime, and observing the hundreds of sail boats docked off of Lake Pepin at nearby Lake City. I've taken more than a dozen New Year's Eve journeys, with no two journeys having been the same over all these years...but this one was still my favorite.

#18. Sioux Falls 2001--My first solo Sioux Falls trip correlated with my peak interest in road trips in general and picking up new towns in particular. With that in mind, I took the opportunity to get off the freeway more frequently and take in a few nearby towns in southwestern Minnesota I had not yet visited, including Lakefield and Ellsworth, among others. The result was a much longer road trip to and from Sioux Falls than what I was used to. Now normally I get restless towards the end of long road trips, but not this one. For whatever reason, even after all those hours, I was in a chill state of mind and driving under 55 even in the home stretch that evening. My best Sioux Falls trip in several years.
Defining music: Carolyn Dawn Johnson "Complicated"

#17. Austin-Owatonna 2001--This is normally my least memorable road trip every year, a three or four-hour retread of my dad's vinyl repair summer in towns very close to home that I usually either do in late August or Labor Day weekend. But everything was always a little more exciting in 2001, the year I shook up my routines and explored some new area. For this trip, I went northwest from Owatonna to revisit Morristown and some unexplored backroads in Rice County. And instead of eating at Arby's in Owatonna like I had always done in the past on this trip, I dined on broasted chicken at The Broaster in Faribault, a family favorite that I loved dining at solo, and have returned to every Austin-Owatonna trip since.
Defining music: Rascal Flatts "Till You Loved Me"

#16. Southern Iowa 2006--For the previous six years, my tradition in April or May was to road trip through the Minnesota River Valley, but having exhausted every conceivable path on that trip and having moved to Des Moines, Iowa, in January 2006, it seemed like a good opportunity to add a different route in the spring. My choice was new territory in southern Iowa and northern Missouri, specifically places my dad told me about when he was on the road with the railroad in the 90s. The culture immediately changes south of Des Moines, and it was intriguing to visit the extremely rural and often impoverished small towns of southern Iowa, seeing the ever-present Amish buggies which looked like eerie Grim Reapers approaching on the gloomy Saturday morning, along with the twangy southern voices that became more prominent the further south I went. I hadn't been to Missouri since 1984 so it was pretty exciting crossing the line and later venturing to Chillicothe and Trenton, two decent-sized towns my dad mentioned while working on the railroad, and then heading north through Chariton, Iowa, hometown of Hy-Vee, the grocery store that is my mom's employer. All in all, a very insightful and exciting trip, with only one nagging downside. It was an ugly and gloomy day with spurts of heavy rain that really sucked away some of the energy of the day. In retrospect, it's hard to understand why I didn't just pick another day for this trip. Whatever the case, it was a great segue to a new road trip tradition exploring new parts of Iowa and Missouri every spring.
Defining music: Kellie Coffey "Texas Plates", Mark Wills "Hank"

#15. Trans-Faribault County 1994--My family visits the gravesites of relatives west and southwest of where I grew up on Memorial Day weekend every spring. In 1993, we visited a few towns on the east side of the neighboring county and unofficially began a tradition that became official the following year as we explored further into Faribault County, a quintessential farm county with lots of attractive little towns. The atmosphere was just perfect for this trip, in my dad's old truck without air conditioning on the hottest Memorial Day I ever recall with temps in the low 90s. It was the perfect segue to the beginning of one of my favorite summers which was only a few days away from kicking off. I've gone on this trip on Memorial Day weekend every year since and it always has some energy being the gateway to summer, but never have I enjoyed the trip as much as I did this year. Icing on the cake was visiting my grandma's place on the drive home and watching a Knight Rider rerun on cable.

#14. Buffalo Ridge 2005--A road trip that started out as a question mark due to the weather became one of my all-time favorites. Usually I take this trip in late March or early April, on the first nice Saturday of the season, but it was March 5 that I set to the highway for this trip, the earliest ever, due to a particularly nice forecast. It was foggy for the first two hours, but as predicted, the sun broke out and the temperature soared as I got closer to Minnesota's majestic southwest corner. I have a rotating route for this trip and this year's just happened to take me to Marshall early in the day and down to the south side of the Buffalo Ridge near Chandler and Edgerton by afternoon, which is one of my favorite routes for this annual trip. Everything was going well, but on the drive home I discovered a classic country station based out of Slayton that was playing a litany of great country songs from generations past one after another. A trip that was already an absolute hoot got that much better.
Defining music: Kathy Mattea "Eighteen Wheels and a Dozen Roses"; Merle Haggard "If We Make it Through December"; Anne Murray "Lucky Me"; Don Williams "Tulsa Time"

#13. Northern Minnesota 2002--For quite some time, I'd been planning an opportunity to make a journey back to northeastern Minnesota, where I hadn't been for nearly 10 years at that point, and specifically to navigate Minnesota State Highway 23 which cuts from Duluth in northeastern Minnesota through central Minnesota and all the way down to the state's southwestern corner, encompassing a huge swath of territory and enabling me to score three dozen towns I'd never been to before. The timing of this road trip was particularly therapeutic, taking place in mid-September 2002 after a bruising breakup with long-distance girlfriend Dana and nearly a month of being the only reporter on staff at the newspaper before a new editor was hired that week. The trip lived up to expectations, with high points being the reacquaintance with Minnesota's north woods, seeing the paper mills and freshly cut timber lying next to the railroad, a typically delicious meal at the Taco John's in Cloquet followed by listening to a Twins game on the radio during their 2002 playoff run, and on Sunday, a pleasant and sunny drive down Highway 23 taking me to a number of new towns as well as different perspectives on towns I'd already been through but had never driven through on Highway 23. Listening to a classic country station from St. Cloud playing some golden oldies from generations gave the day some extra atmosphere.
Defining music: Andy Griggs "Practice Life", Johnny Horton "Sink the Bismarck", George Jones "Who's Gonna Fill Their Shoes"

#12. Buffalo Ridge 1998--A new road trip tradition began spectacularly on spring break of my sophomore year of college. I had never been anywhere in southwestern Minnesota north of either Highway 90 or Highway 60 and was clamoring to get there. My dad hadn't been called back to the railroad yet and I talked him into going to the Marshall area on a nice late spring day in late March. I immediately fell in love with the area and it was at this point, after scoring 15 new towns on this trip, that I officially decided it would be an interesting effort to try to get to all 734 Minnesota communities, so that gauntlet was effectively laid that day. Navigating the new territory gave me a renewed appreciation for my love of the wide open spaces of southwestern Minnesota and the Norman Rockwell look of many of the area's small towns. Up to this point, I was content to largely retravel my existing list of road trips year after year, but this was the trip that got me interested in visiting new places and conquering more Minnesota territory. From this point forward, no spring will go by without one of my several variations on this southwestern Minnesota voyage.

#11. Trans-Freeborn County 1990--One of my first road trips of all came together off the cuff on a Friday morning the day after Thanksgiving. I was in Albert Lea with my dad, drinking a can of Pepsi from one of their winter cans collection of 1990 and on a lark requested my dad take a little journey through the western side of Freeborn County to visit towns I'd never been to before. My dad's not one to go on "dry runs", very much unlike myself, so he said he'd do it if we got our pheasant-hunting gear and turned into a hybrid road trip/hunting safari. It was a good compromise and I enjoyed the drive through previously unexplored towns in western Freeborn County like Conger and Mansfield. We then stopped and visited my grandpa who lives on the Minnesota/Iowa line in southwestern Freeborn County and stuck around about a half hour. My dad was gonna take me home on a back road but missed his turn and we ended up deciding to visit more territory in southeastern Freeborn County, picking up several more little towns like Myrtle, London, and the memorable Deer Creek on the state line, which featured two houses, an abandoned creamery, and an abandoned general store complete with swinging door. Twenty years later, there is no evidence remaining that a town ever existed where Deer Creek once sat as it's all been plowed over. It was a fascinating approach to what would become my first road trip tradition and it certainly ignited a fire in me even at age 13 and has kept the tradition alive.

#10. Sioux Falls 1994--I didn't go to Sioux Falls at all in 1992 and was beset by terrible fog for the 1993 trip. I was overdue for a great Sioux Falls trip and got one in 1994, one of my favorite summers. It got to about 90 degrees, which is perfect weather for me on this quintessential summer trip, back then taking place in late July. My dad's truck was under repair so we took his buddy's old wreck of a Ford, which provided a unique memory of its own for this trip. It was on this trip that I got my first indication of the depth of the Hispanic population explosion in certain southwest Minnesota towns, particularly Worthington and St. James. Particularly back then, when my lineup of road trips was both in its infancy are far less extensive than it is today, there was no better feeling that coming home after a full day road tripping to Sioux Falls, bringing back all those great memories of the vinyl repair summer of four years earlier.

#9. Western Hump 2001--Purely by chance, a wedding in west-central Minnesota allowed me the opportunity the prior summer to take a road trip to the Western Hump of Minnesota and its surrounding area, allowing me to score dozens of new towns. As I often do, I wanted to try to capture lightning in a bottle again this summer, and came very close to pulling it off with another of my classic road trips. I shook up my route, going to a few of the same places as the summer before that I liked best, but going to multiple new places as well. The first day was full of speed bumps, with torrential rain in the first couple hours of the drive finally yielding, an attempt to meet a friend at a bible camp near Slayton, Minnesota, who I never was able to find, and getting pulled over for the first time in my life and accused of not wearing a seatbelt even though I had been (I must have convinced the cop...didn't get a ticket), but from there things went smoothly as I rented a motel room in Dawson, MN, and watched Miami Vice reruns on cable that evening. The next day, the weather was perfect as I explored my favorite communities on the trip in Minnesota's western hump and took a decidedly different route home through a bunch of additional unexplored terrain and scoring 17 new towns. I always love this trip in mid-to-late July but I've never had as good of a time in the years since as I did those first two years.
Defining music: Mark McGuinn "That's a Plan"; Phil Vassar "Six Pack Summer"

#8. Northern Minnesota 2003--I found a perfect balance on this road trip, with an extremely ambitious haul that took me west to east and then back in northern Minnesota, staying overnight at Grand Rapids, and scoring an astounding 47 new towns over two days, but not burning myself out with a route that was too ambitious. It was first time in more than decade that I had been to a number of places I visited on this trip in northeastern Minnesota (Aitkin County and the aforementioned Grand Rapids) while I had never been to several other places on the trip, particularly in northwestern Minnesota where I visited Moorhead and Crookston for the first time. And for most of the second day, I got a special treat journeying down I-29 in eastern North and South Dakota for nearly 300 miles, particularly impressed with the continental divide in South Dakota's northeastern corner. 2003 had been a pretty glum year for me in its first half but had really taken flight by this time of the year, with this very memorable road trip being part of 2003's heroic comeback.
Defining music: Ashley Gearing "Can You Hear Me When I Talk To You?", Josh Turner "Long Black Train", Darryl Worley "Tennessee River Run"

#7. Northern Minnesota 2004--It was a close call whether I loved the 2003 Northern Minnesota trip more or if the 2004 encore would trump it. I narrowly decided in favor of the epic three-day 2004 journey. Taking place in mid-September 2004, the trip added an extra dimension of fun as a lot of places already had yard sign wars between Bush and Kerry in the most exciting election campaign of my lifetime, and it was a blast seeing the turf war play out in western Minnesota where most of day one of the trip took place, and in heavily Democratic northeastern Minnesota where most of day two took place. I visited every town in the Iron Range for the first time on that second day before taking a very windy back road westward through northern Minnesota. I was thankful that I was the only car on the road because the road wouldn't have been nearly as fun with another car trailing close behind. My original plan was to trek through the isolated Red Lake Indian Reservation, but a native of a nearby town advised me only three days earlier not to even drive through Red Lake because of its hostility to outsiders. That was red flag enough for me and I complied by driving around the reservation and then towards the North Dakota border from there. I stayed overnight in Fargo and on day three explored some new terrain in the eastern Dakotas, including Valley City and Gwinnett in North Dakota, and then Webster and De Smet in South Dakota. This was the same year as the epic Daschle vs. Thune Senate race which made for some humorous radio ads and exciting yard sign wars, albeit somewhat misleading given that this is the most Democratic part of South Dakota. From there, it was an exhausting final couple of hours driving home to my apartment in St. James after this long but extremely worthwhile three-day detour.
Defining music: Jimmy Buffett and Martina McBride "Trip Around the Sun"; Restless Heart "Feel My Way To You"; Shania Twain and Billy Currington "Party for Two"

#6. Southern Iowa 2007--It was mid-May before I was able to organize my masterpiece of getting my then girlfriend Elise to tag along on my southern Iowa road trip. Unlike the prior year, I got a really nice day for the journey, which included some of the same areas just south of Des Moines to the Missouri border, but I went east from there to towns such as Centerville, Bloomfield, and Ottumwa. Elise was a great road companion in multiple ways and proved that just the right company can turn a good road trip into a great road trip.

#5. Dakota 2008--The high point of the summer of 2008 was my first voyage to the Black Hills in a quarter century (literally...I hadn't been there before since 1983). I had taken these journeys to South Dakota for five years at this point and had even crossed the Missouri River into the western part of the South Dakota a couple of times in those previous trips, but had never gone past Murdo to the area where South Dakota changes dramatically. And over a compressed time period, I took in a great deal of the Black Hills experience and even captured it on film, buying a throwaway camera at Wall Drug, and then visiting the outskirts of the Badlands, Mount Rushmore, Sturgis, Deadwood, and the loop of the densest Black Hills from Deadwood to Spearfish where I stayed overnight. The next day I journeyed across the state line into Wyoming and almost hit two deer on the freeway. From there I traveled home on Highway 12 through remote northern South Dakota, an area most people wouldn't find much to like about but which I adored given the region's incredibly sparse terrain...the last place I expected to see a hot blond road construction worker who I got to flirt with while waiting for the pilot car to take me through the town of Dupree on the Cheyenne River Indian Reservation. It was exactly what the doctor ordered that summer and a nice return to the Black Hills after such a long time away.
Defining music: Luke Bryan "Country Man"; Jessica Simpson "Come On Over" (her lone country hit)

#4. Buffalo Ridge 2000--Only a few of my road trips can be looked back upon as moments of pure perfection, but this April 2000 road trip to southwestern Minnesota taken a month before my college graduation was one of them. I was planning to go myself and was surprised when my mom asked if she could come along. She's not much for road trips but it turned out to be a barnburner, a steamy 90-degree day that added perfect atmosphere to this adventure where my prior acquaintance with southwestern Minnesota was just enough to have a vague sense of what lied ahead but not well established enough to keep it from seeming fresh and original as I visited some of my favorite towns and discovered a handful of new ones in the Canby area. We stopped for lunch in Pipestone and explored the prairie highlands of Lake Benton and got stuck behind a train in St. James, the town that would be my home two short years later. This was the textbook perfect road trip and enough to make me wish my mom tagged along more often.
Defining music: Phil Vassar "Carlene", Yankee Grey "Another Nine Minutes", Lee Ann Womack "I Hope You Dance"

#3. Dakota 2003--Here was a road trip nearly three years in the making that I had neither the time nor the money to partake in up until my first vacation week from the newspaper in August 2003. The trip was planned out like a military operation and everything went breathtakingly well. I felt the energy soar as I passed Sioux Falls on I-90 for the first time since I was a little boy. The rest of that first day consisted of my first voyage to the Corn Palace in Mitchell, and points northward and westward from there including the most remote stretch of highway I had ever encountered up to that point in my life north of Highmore, SD, a 36-mile stretch of highway with only three homesteads. And all this transpired amidst 105-degree heat that wasn't as oppressive as one would expect given the limited humidity in central South Dakota. I stayed overnight at Aberdeen, hometown of Tom Daschle, and a town that left a considerable impression on me. Day Two took me to North Dakota through Jamestown and up to Devils Lake through the nearby Indian reservation and around the scenic lake itself just south of town. From there, I journeyed northeastward into far northwestern Minnesota, where I would score a flurry of new towns in the state's furthest northern reaches driving just across the Rainy River from Canada en route to International Falls where I stayed overnight for night two. It was 97 degrees that day, the warmest day in International Falls in more than a decade, and I remember burning through pop and bottled water by the jugful in the much stickier hit of Minnesota. The final day took me through the Iron Range and points southward through east-central Minnesota where I scored a half dozen or so new towns before wrapping up the road trip and returning home for the rest of my vacation. I said before that 2003 had been pretty weak up to that point, but this burst of energy was exactly what I needed to turn it around. I've gone on different vacations to the Dakotas almost every year since, but nothing has matched the magic of this rookie voyage, a trip that lived up to expectations completely after three years of build-up.
Defining music: Billy Dean "I'm in Love with You", Jennifer Hanson "Half a Heart Tattoo", Toby Keith "I Love This Bar"

#2. Western Hump 2000--The life-changing trip made possible through the wedding of my college roommate in Montevideo, Minnesota, where I stayed overnight. The summer of 2000 was my second favorite of all-time and as good of a time as I was having with it up to this point, this epic two-day trip was the segue to an even better second half of the summer. The journey to Montevideo was exciting in itself and the wedding went nicely, but it was the next day I was looking forward to most, scoring a motel room on the western edge of Montevideo and waking up that Sunday morning to see the sign for towns westward that I had been looking forward to getting to for years prior, and was finally about to get to. The energy was palpable, and it lived up to expectations completely. Most impressive was the western hump of Minnesota itself, a geographical anomaly on the cusp of a continental divide, with a breathtaking long-distance view for many miles into South Dakota. I scored more than three dozen new towns as I trekked through my well-planned route across west-central Minnesota through new towns like Wheaton, Morris, and Glenwood, before heading east to even more new towns such as Paynesville and Litchfield, all while traveling in my past-its-prime 1978 Ford Fairmont guzzling gas. Thankfully gas was only $1.25 a gallon back then. The whole trip was a hoot and my life was about to change in a profound way soon after my return.
Defining music: Vince Gill "Feels Like Love", Sons of the Desert "Everybody's Gotta Grow Up Sometime", Restless Heart "Back to the Heartbreak Kid"

#1. Sioux Falls 1991--I said at the outset that the Sioux Falls trip was the granddaddy of them all. It wasn't technically the first road trip I ever took, but it was the first planned as a road trip. I was one year to the day removed from the vinyl repair summer with my dad and had intense nostalgia to revisit. It was finally happening, and amazingly enough, my dad got a request from a dealership in Windom to do some work even though he had technically ended his vinyl repair gambit. But since he still had the supplies on hand, he was doing the work for a little bit of pocket change and it was downright eerie that it played out at the exact time needed to lend this road trip the perfect retro authenticity. We journeyed west on I-90 and the same good vibe that defined the summer of 1990 came rushing back and went into all the little towns to see all the car dealerships we had patronized the previous year. We never went all the way to Sioux Falls before, but it seemed like a worthy destination and gave us the opportunity to eat at Arby's, which as I said was a big deal for me at the time. On top of that, we went briefly into the Empire mall in Sioux Falls and I looked at the new TV Guide in the bookstore featuring an article about the upcoming seventh season of MacGyver. The weather was mid-80s, sunny, and perfect and the entire day was a perfect mix of new and nostalgia. Seems difficult to ever top this road trip for pure perfection.

So there's my list. There will undoubtedly be future road trips that will infiltrate this list. I have such a deep attachment with the road trips from the upper rungs of this list that they could very well stand as my all-time best for the duration of my life, but you never know when you set off for a road trip which ones you'll never forget. That's part of why I continue to go on them...as you never know which of them will remain in your soul forever.