Preparing for a Solo Road Trip
In a little less than a week, I’ll be in a rental car on my way to Asheville, North Carolina. Here’s how I picture it: windows rolled down, sunglasses on, loud music on the radio, and me carefree and cruising confidently down I-65. I don’t think I am actually capable of being that carefree, but I’m hoping to at least enjoy the ride. While I am very excited that I am heading off on my own to explore a chunk of the US, I also have no delusions that I can just pick up and go without some sort of plan. I made my hotel and car rental reservations months ago, and mapped out my route from Chicago. I have the basics down, but there’s still a number of things I need to check off my list before I can embark upon this adventure:
First, and most importantly, snacks. No road trip is complete without a good supply of treats to keep you nourished between pit stops. I typically need salty snacks, like Chex mix or pistachios, and some sort of fruit to keep me going, plus plenty of bottled water, of course. I always pack a box of granola bars to have for breakfast while I’m on vacation to save some money on eating out. I am planning on packing a lunch as well, so I don’t have to stop as much on the way.
A fun, upbeat playlist is essential to any road trip! My trip is going to be around 10 hours from Chicago to Asheville, so I’m working on the ultimate mish mosh of tunes that I can sing along to. I’ve already started on my Road Trip playlist, but it needs a lot more work to try to fill that time slot. Also, because the drive is on the longer side, I’m also playing with the idea of getting a book on tape from the library to help pass the time (any suggestions??).
I know it will be hot in Asheville, and I’ve already started to put aside some hot weather clothes to pack. I also know I will bring too much, as per usual. But, that’s part of the beauty of a road trip: no checked baggage fees! Everything that I have set to bring on this trip already is hoarded on my desk at the moment. In a couple of days I’ll have to get it together and put everything into my suitcase and backpack to be ready to go. Because I am prone to forgetting things when I pack, I always make a checklist beforehand to limit the things left behind.
I have been doing some light research on the local attractions and dining options, but I need to figure out my must see/eat places. I don’t like to go in to a trip with a completely planned out itinerary, but I do like to make a small list of things I absolutely want to accomplish while I’m there. Currently at the top of my list are The Biltmore Estate, The Orange Peel, Chimney Rock, and exploring downtown Asheville. I like to use google maps to see which attractions are close to others so I can lump them in together in one day. I am working with three days to enjoy an amazing city with a lot of activities to choose from so a girl’s gotta have priorities.
While I am fairly confident in my driving abilities, and fully confident in my ability to take care of myself, there will always be ways to limit any travel safety risks. I am putting together an emergency kit for the car, which will include: first aid supplies, jumper cables, pepper spray, and an atlas in case Google maps fails me. I also am bringing along a door stop, a tip that I stole from the Young Adventuress, to secure my hotel room door. I already gave my family and boyfriend my hotel information, and plan to check in with them each day. The best thing I can do to keep out of any weird situations is to simply pay attention.
Over the next few days, I’ll (hopefully) have a good handle on all these things. I am so excited to be on my way, and I can’t wait to tell you all about Asheville when I get back.
If you have any tips for solo travel or road trips or even audio book or music recommendations, please share them in the comments!
We go to Maiden Lake in Wisconsin every year for Independence Day, it’s a family tradition (as per my previous Lakewood, WI post). This year, I drove up with my boyfriend straight from Chicago, which was a first. We left at 6:30am on Friday, stopping for coffee first and then we were on our way. It was an easy five hour jaunt up through Milwaukee, Green Bay and straight on to Lakewood. We arrived just before noon and got ready to go on the boat 
right away. It was a perfect day to go out on the lake, warm enough to make you want to jump in the water but with a perfect breeze. We cruised around for a bit and then stopped for cocktails and snacks, which were stored in the coolers. It was a perfect afternoon of lounging out on the water. After snacks, I was talked into trying to water-ski, which was a painful failure. If I didn’t get a mouthful of lake water getting pulled directly out 
of the skis, I was flying backwards with the skis pulling my legs out to the sides. I did manage to get up halfway on the skis once, but I got so excited that I flung my hands up in the air, effectively letting go of the rope. I called it quits after that and we headed back to the cabin to tie up the boat and get ready for dinner. There are a lot of great restaurants and supper clubs around Lakewood, but because of the holiday weekend and the size of our group, it’s usually easier to make dinner at home. The end result is always delicious, and enjoyed on the porch in good company. After dinner a few of us walked from the cabin to the Maiden Lake Supper Club to enjoy a drink al fresco on their deck by the lake. The Supper Club is a Maiden Lake institution and is really the only the restaurant that’s actually on the lake.
There is always a wait to enjoy their large portioned, comfort foods and seating in the bar and on the deck is always limited. Luckily, we were able to get a table and enjoy the sun setting over the lake. On our walk back, we admired the other cabins along the lake. Some were 
newly built, and some maintained their rustic charm. My favorite had a small red box on a post with the title Maiden Lake Library on it out front. Its front window displayed an array of books, with take one leave one written under the shelves. We came home to a giant bonfire behind the house primed and ready for s’mores making. It was a perfect ending to our first day at the lake. The next day was July 4th, and I woke up early to paddle-board before the bigger boats came out. It is the most peaceful thing to be out in the middle of the perfectly-still lake on the paddle-board. After I got my fill of inner peace, we started our Independence Day celebrations early with a huge breakfast. The best part of 
lake life is that everything revolves around when we can get out on the boat. While half of us cleaned up from breakfast, the rest of our group readied the boats to take them out for the day. We set shortly after, split between two boats. I tried to ski again, and this time I was finally successful! I got up for a while and was satisfied enough to quit while I was ahead. The boats met up to anchor and so we could swim and sip cocktails in the sunshine. When we docked for the day, my boyfriend and I went to the grocery store for burger fixins and then drove down the road to Sweet Memories, an amazing candy store in Lakewood. 
contestants did not disappoint. There were Minions, Pirates, Winnie the Pooh, and even Snow White and her seven buddies showed up for the occasion. The next holiday festivity was our annual trip to the best ice cream stop in the Midwest, Northern D’Lites. They have delicious soft serve in an ever changing cycle of flavors and all the usual suspects as far 
as frozen treats go. It’s a humble pick-up window surrounded by picnic tables, complete with friendly staff and a long line of customers. After our collective sweet tooth was satiated, we drove off to find parking for the fireworks show, which we watched in the back of my uncle’s pick-up truck. The fireworks display is always great, and this year it was the same. However, the 
next day, we were assured by one of the grocery store clerks at True Value that this year was a little lean because next year is the town’s centennial, which they will go all out for. Our last day at the Cabin, my boyfriend and I spent the morning Kayaking to one of the beautiful inlets on the south side of Maiden Lake. Our whole crew had one last spin around the lake in the speed boats and one last swim before we put away all of the boating gear, took the boats out of the water, and closed up the cabin. It’s always sad leaving, but hopefully we’ll be back sooner rather than later. On our way home, my boyfriend and I stopped at two vastly different but equally important Wisconsin landmarks. The first was Bagley Rapids in Mountain, WI and the second was Mars Cheese Castle in Kenosha, WI. Bagley Rapids is a beautiful park and campground in the Nicolet National Forest.
We had to drive down a very narrow, dirt road to get to the parking lot, which was very small and perhaps the wrong parking lot. However, we finally made it down to the rapids, which we heard before they came into view. It was a gorgeous scene. We were able to take a walk along the side of the rapids before we had to get back to the car and continue on home. We drove for another three hours before reaching Kenosha, the location of the famous Mars Cheese Castle.
I’ve passed it many times without exiting the highway to visit, but this time we exited route 94 and pulled into the parking lot of the castle. It is a mecca of cheese, sausage and condiments. It is also one of the last stops on the highway to pick up some New Glarus beer, which is only available in Wisconsin and so delicious. I have to say, it was pretty expensive compared to other stops ($3 extra for a 6-pack of Spotted Cow). We purchased some cheese, sausage and beer regardless of the price and stopped in the restaurant for a bite to eat before finishing the drive to Chicago. We both had bratwursts, which were very good, but the service was slow and without a smile. The rest of the drive went smoothly, and soon we were home safe and sound. Before long, I was asleep, dreaming of being back at the lake.
entered the Visitor Center only to grab a map and hit the restrooms before we began our hike. Originally, we wanted to hike up to the Lodge first, to get some lunch and figure out which hikes we wanted to do. What actually happened was we wound up on the Wildcat Canyon overlook trail. The paths were muddy due to days of rain prior to our visit, and my Chuck Taylors proved to be a poor hiking footwear choice. Actually, my whole outfit was ill-suited to nature and now I know better. Please note that jean shorts are not a great choice for four hours of humid hiking through the forest. What can I say? I’m a city girl. Luckily, the scenery was so gorgeous that I soon forgot my wardrobe woes and was able to focus on the views. We reached the outlook and noticed there were people hanging out in the canyon below, basking in the sunlight and playing beneath the waterfall, with no indication of how they appeared there. I made it my personal mission 
for the day to be one of those people. The weather was perfect, and everything was so green and gorgeous. It was nice just to be outside. Eventually, we found a sign pointing us towards the Lodge. The area surrounding the lodge was crowded with hikers and overnighters, staying in either the Lodge Hotel or the cute little cabins in the same general area. The lodge itself was a stately and beautiful large, wooden structure. I instantly wanted to stay the night there. We decided to have lunch in the “Dining Room” instead of the small café in the lobby. The dining room was also very large, with an outdoor deck attached. It had a romantic feel with the dark wood, soft lighting, and large fireplace holding court in the back of the room. The lunch menu included comfort food entrees, salads and sandwiches. We both ordered the Illiniwek Chicken Sandwich. The waitress was not the friendliest person we’d met that day, but the
service was prompt and the food was delicious so we overlooked her surly demeanor. After lunch, I stopped at the front desk to inquire about vacancy and room rates. Unfortunately they were completely booked, but the good news is their prices are completely affordable with their standard rooms starting around $100 and their cabins starting at $125 (depending on the season). We vowed to come back and stay in a cabin in the near future. We hiked up to the park’s namesake, the actual Starved Rock, and the stairs up to the overlook were no joke. The view from the top was breathtaking (minus the huge dam that was visible on one side of the Illinois River). The path at the top of Starved Rock wound in a circle, through trees and wildflowers looking lush from the summer rain. We meandered back down the way we came, past other hikers huffing and puffing up the many, many stairs. From there we hiked up to the Lover’s Leap overlook, which offered an amazing view of Starved Rock and the river 
below. It was finally time to complete my mission of the day and find the way into the canyon that we had seen from the trail above. We found the path and made our way along the river to the canyon. We could hear its current visitor’s voices bouncing off the rock face in what could only be described as shouts of glee. When we finally reached Wildcat Canyon, it took some maneuvering to get over to the waterfall, through the water and mud. Once we were finally in the main clearing, I took my shoes off and stuck my feet in the water. It was cloudy with the sand beneath, but cold and refreshing. The waterfall was gorgeous; it flowed into a small pool teaming with happy little hikers. Though the area was crowded, there was a solidarity among the visitors in the canyon; everyone was admiring the view. It was hard to leave such a beautiful place, but it was about that time to head back to the visitors center. Overall, we hiked about five miles through the forest, up and down stairs, and on gorgeous overlook boardwalks. By the time we made it back to the car, I was exhausted, but already planning our next visit. Even with how much we had already explored, there were still so many other paths, overlooks and canyons to see. I’d imagine that not too much time will pass before I’m back for more.
We walked down 5th Avenue and around in a loop past Rockefeller Center and the fancy shops and wound up in a café named Papillion. The ground floor looked like a typical bar on a Friday night. Once we were seated and viewed the menu (and the prices), we decided to have drinks and appetizers. I ordered white wine and my sweet ordered whiskey and we both split the charcuterie plate. The atmosphere and the cured meats were lovely, and we enjoyed our time at Papillion. We left the restaurant and continued our wandering about midtown. The charcuterie didn’t hold us for long and we decided to enjoy another small plate at another café, this one closer to the hotel. It was called Benoit and it was perfect. We sat in the bar, which looked like the set of a Woody Allen movie, and ordered coffee and dessert. We got a slice of chocolate tart and 
hop on a subway train to the World Trade Center Memorial. We got off the train with a sea of people and followed the tide to the site of the memorial. It was a very emotional experience despite the multitude of selfie sticks. The memorial itself was beautiful; the reflecting pools are quite the sight to take in. We walked from the memorial to Battery Park, stopping at St. Paul’s Cathedral and Trinity Church along the way. The churches were so pretty, we couldn’t help but peak inside and gaze at their beautiful structures and stained glass windows. We finally made it to Battery Park and were amazed at how saturated it was with tourists. We deliberately walked past the line for Liberty and Ellis Islands (the lines were out of control) and made our way to the (completely gratis) Staten Island Ferry at Whitehall Terminal. We had to wait for a ferry, but grabbed a giant pretzel at one of the many vendors in the terminal to pass the time. Once the ferry arrived and we were able to board, it was a mad dash to the window that would be the best vantage point to see the Statue of Liberty. We grabbed some seats on that particular side of the boat and got up to join the crowds once it was close enough to the statue. We stayed on Staten Island only long enough to board the next ferry back to Manhattan. 
of tourism. My lovely boyfriend procured a pair of tickets to see Phantom of the Opera that evening, so we dolled up and went to dinner in the Theater District before the show. As it was an hour before show time on a Saturday night, and we did not have reservations, we sat at the bar at Café Angus Bistro to eat. We ordered their Du Pre option, which was a prix fixe, three course menu designed for pre-show diners. I chose the roasted buttermilk chicken as my entrée, and Mike had the salmon. Along with the entrée came a small portion of house salad and a delightful three bite portion of dessert, their apple-cherry crumble. The meal was delicious and the perfect amount of food. We went to the Majestic Theater feeling satisfied and ready to take in a three hour performance. The musical was magnificent. I loved every minute of it, and the cast was so talented I wanted to cry. Each scene was better than the last; the whole production was perfect. After the show we wandered around 
the Theater District and Time Square taking pictures and being uber tourists. It was a very surreal experience, being in the middle of all the lights and people, where so many iconic events have taken place. We stopped by Junior’s Cheesecake and shared a slice of the cherry, which we devoured while we continued to walk around. We found that as we were walking past some of the other theaters, the cast was coming out to crowds of people wanting to get their programs signed. We observed the whole scene, and realized we were staring at Mr. Ferris Bueller himself, Matthew Broderick. Of course we couldn’t have him sign a program from a play he did not star in, so we just stared in awe as he signed others’. Once he got in his SUV to leave, we were able to tear ourselves away from the scene and start wandering again. Being the Stephen King fan that I am, I convinced Mike to walk to 46th and 2nd Avenue to where the vacant lot that houses The Rose from the Dark Tower Series is supposed to be located. It was quite a long walk from Time Square, and it’s probably the most fangirl thing I’ve ever done, but it was totally worth it. There was no 
vacant lot, only a small park with a bodega across the street. Mike very thoughtfully bought me a rose at the bodega and we placed it behind the locked gate of the park (only to take it back after I took a picture). That rose cost us $18 because we didn’t have any cash and there was a minimum for debit card purchases, so we got The Rose and a 6-pack of Brooklyn Lager. It made me very happy though, to make the small pilgrimage to an iconic spot in my favorite author’s books. After I got my fill of Dark Tower fanfare, we walked back to the hotel the long way, enjoying the weather and each other’s company. We turned on the TV in the room and each drank a lager while discussing the day’s events.
rides and attractions to decide which to spend our money on. Each ride was about $4-$9, so we only went on three. First we tried one of the small roller coasters, called The Tickler, and we went on the swings before we walked over to the main event, The Cyclone. The cyclone is an almost century old, wooden roller coaster, that is as rickety as it sounds. We felt we absolutely had to go on it. There was no line, and we climbed the wooden steps up to the boarding platform to get in one of the leather-lined cars right away. A few other people boarded, and we took off through the sea of wooden slats and planks. It only lasted a couple of minutes, but it was very fun, and provided a great view of the coast. We walked around a little longer, and then got back on the train to head back towards the city. We made a pit stop at Washington Square Park and walked to The Strand Bookstore in the East Village. 
finally made it back to the hotel, we readied ourselves to go meet one of my very good friends for dinner in Hell’s Kitchen. We met him on the corner of 50th and 9th, and decided we were all in the mood for margaritas. We waltzed down the street into Arriba Arriba, and were seated right away, surprisingly. We all ordered frozen margaritas; mine was watermelon. The margs were delicious and the food was even better. We had two rounds and were delightfully tipsy when we left the restaurant to walk back towards the hotel. We met more Chicago colleagues at the hotel bar, Salon De Ning, which was on the roof. 
We got a large table in the corner of the outdoor terrace. It was a chilly night, but the terrace was spotted with heat lamps and the cocktails helped as well. The drinks were a little pricey but delectably worth it. We finished the night off back at Cassidy’s Pub and enjoyed the drinks and company just as we did the first night there.
New York Public Library. It was gorgeous, both inside and out. We toured the inside, independently, and walked through the reading rooms. The Rose Main Reading room, which is what I wanted to see, was unfortunately closed for remodeling, but at least it gives me a good reason to revisit. After we left the library, we walked down 5th Avenue towards Central Park. We decided to have lunch first then take a stroll through the inside of the park. We walked along Madison Avenue, 
amongst the designer stores and boutiques, and could not for the life of us find a place to have lunch that wouldn’t cost us the equivalent of our plane tickets. We finally came upon 3 Guys on Madison Avenue, which fit the bill perfectly. We had sandwiches in a booth at the front of the diner. I later read, on the plane ride home, that Joan Didion and her late husband used to stop in there regularly (from “The Year of Magical Thinking”) , which made the experience that much better. We finally made it to Central Park and walked around for a few hours, stopping by Alice in Wonderland and Hans Christian Anderson to take
pictures, and by the Bethesda Fountain to watch the brides and grooms pose and listen to the small choir singing under the bridge. We walked back to the hotel to collect our luggage and took the subway to JFK. The whole while I complained and dragged my feet, because I did not want to leave. Every time I go to New York, I come home and start planning my next trip back, whether it be in a few months or a year, almost as soon as I get off the plane. We have a great long-distance relationship, New York and I, and every time I go back, it’s as if I never left.
main trail that I would wander out on in hopes of seeing a huge gator, halfway submerged in the water, looking dangerous. However, these jaunts were fruitless. Finally, halfway through the walk, a group of other hikers pointed out a baby gator floating right off the boardwalk. We marveled at it briefly and then hightailed out of there before the mama gator came after us. The walk back to the entrance of the trail was grueling and hot. We had to pick up the pace so that we could make our afternoon steamboat cruise. We speed walked back to the car, ducking under spider webs and hopping over snake tails. We made it back to the river with just enough time for Michael to park and for me to get us two slices of pizza and a hurricane to share before we boarded the boat.
wanted to explore. It looked beautiful from the outside, and I couldn’t wait to see what it had in store for us. We valeted the car, and dragged our luggage in towards the front desk. When we checked in, the front desk staff wished us a happy anniversary and informed us that we had a room upgrade, which was a wonderful surprise. We schlepped all of our luggage up to the room (working at a hotel makes me reluctant to ask for help when staying at other hotels). It was a beautiful room with a huge bed covered in cloud-like linens and a comfy arm chair in the corner. As soon as we settled in and started unpacking, there was a knock at the door. The front desk manager had brought us a bottle of complimentary champagne to help us celebrate. We toasted ourselves and got ready for dinner. The bathroom was gorgeous, covered in marble, with a huge tub and a big enough vanity so we could both primp.
water and fresh bread rolls. We both ordered local beers and decided to order spicy fried alligator and the boucherie plate, which included a daily special of charcuterie and accouterments. The food was so delicious and flavorful. For dessert, we decided on peach cobbler with vanilla ice cream and coffee to pull us up from our food coma. The peaches tasted so fresh and the coffee hit the spot; we were ready to get back out there and explore. We wandered around the warehouse district, which was an interesting mix of industrial buildings and clubs. When we passed the Harrah’s casino, we decided to go in and each gamble $5 with the hopes of doubling our vacation budget. Surprisingly, that didn’t happen, but it was definitely an experience. Smoking was allowed in the casino, which made the air cloudy and thick. The personas of the gamblers ranged from little old ladies to cigar smoking hit men. We gingerly picked our way through the dime machines and lost all of our allotted money, then snuck back out with our heads down. After that, Michael and I decided that a night cap was in order, so we picked a bar at random and sat at a high top by the window. True to form, I had a gin and tonic, and he had a Jack and coke. We discussed our plans for the rest of our trip and people watched from the window before heading back to the hotel for the night.
We woke up the next morning to rain streaming down the windows. Michael made some coffee and we decided to venture out anyways. We huddled close under the umbrella and hurried from awning to awning. New Orleans looks so romantic in the rain, so it was an enjoyable stroll despite the weather. We walked over to Bourbon Street and marveled over the long-standing architecture that contrasted beautifully with the bright neon signs that marked each bar and club. Along the way, we realized that this particular weekend was Southern Decadence, a festival widely known as the “Gay Mardi Gras”. The banners, which hung from balconies everywhere, promised an exciting weekend. We took a lap around the French Quarter and stopped in many a voodoo shop. The oddities in the shops were all the same, but each one drew us in anyways. Once we had come back to Bourbon Street, we stopped in an unremarkable restaurant with delicious gumbo and crawfish beignets. Once we had refueled we were ready to explore more.
complete with blue strobe light pulsing underneath. Because of the open container laws in NOLA we were able to take our drinks to go and walk towards the river. In the rain, the Mighty Mississippi looked brown and depressing. We turned around to walk back inland and ended up in Jackson Square, where a statue of Andrew Jackson stood in the middle, while the St. Louis Cathedral loomed behind it. The scene was truly stunning. A cobble stone alley ran adjacent to the cathedral; walking down it was like strolling through history. On the opposite side of the alley was William Faulkner’s House, where he wrote his first novel. The first level of the house now contains a quaint book store full of the classics.
Michael got us two hurricanes (add an extra shot for $1, why not??) and we continued our jaunt. The streets of The French Quarter are lined with beautifully colored houses and buildings that made for a beautiful back drop to our boozy walk. We soon found ourselves in Louis Armstrong Park, named, of course, for Mr. Jazz himself. The park was gorgeous, with a stream running through it and statues of great musicians scattered throughout. We played “Only You” on my phone as we took in the loveliness of the park.
On the way back to our hotel (we decided we needed a nap before we went out for the night), we stopped at a corner store/mecca of delicious drunk food called Verti Marte. I had heard about this place from a local, which almost guarantees its five star status. We had the Jazz Sandwich, which was topped with shrimp, ham, turkey and veggies and it was heavenly. We ate it as we walked back to the hotel to nap, rally and head back out into the madness.
along with dollar bills and small samples of personal lubricant and the costumes ranged from creative and cute to one lone leather strap. We went to Maison Bourbon first, to hear some live jazz. The music was excellent and 100% worth the pricey and boring drinks. After a while, we moved on to the next bar, which featured “Huge Ass Beers”, a 32oz domestic beer of your choosing. We took to the streets, huge beers in hand, and wordlessly people watched. It was quite the spectacle. We ended the night at Mango Mango, the slushy/pizza joint, and I have never had a better tasting slice of pizza at 3:00 AM.
weekend. We took a lap around the French Quarter and stopped in many a voodoo shop. The oddities in the shops were all the same, but each one drew us in anyways. Once we had come back to Bourbon Street, we stopped in an unremarkable restaurant with delicious gumbo and crawfish beignets. Once we had refueled we were ready to explore more. It was still raining when we left the restaurant. We continued our wandering, peeking into the alleys that stood perpendicular to the main streets. They contained a number of things, including petite restaurants and art galleries. We stopped in the “famous” Spirits on Bourbon and tried their resurrection cocktail, served in a plastic skull complete with blue strobe light pulsing underneath. Because of the open container laws in NOLA we were able to take our drinks to go and walk towards the river. In the rain, 
the Mighty Mississippi looked brown and depressing. We turned around to walk back inland and ended up in Jackson Square, where a statue of Andrew Jackson stood in the middle, while the St. Louis Cathedral loomed behind it. The scene was truly stunning. A cobble stone alley ran adjacent to the cathedral; walking down it was like strolling through history. On the opposite side of the alley was William Faulkner’s House, where he wrote his first novel. The first level of the house now contains a quaint book store full of the classics. Throughout Bourbon Street and The French Quarter are small restaurants that solely serve alcoholic slushies, jello shots and pizza; aka the only things you will ever need. Michael got us two hurricanes (add an extra shot for $1, why not??) and we continued our jaunt. The streets of The French Quarter are lined with beautifully colored houses and buildings that made for a beautiful back drop to our boozy walk. We soon found ourselves in Louis Armstrong Park, named, of course, for Mr. Jazz himself. The park was gorgeous, with a stream running through it and statues of great musicians scattered throughout. We played “Only You” on my phone as we took in the loveliness of the park.
rebeccawanderlusting 