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USA Travel: Notes From A Solo Midwest Road Trip

An amazing solo road trip in the USA

I’m a restless soul, and am constantly craving a change of scenery or a new adventure to stimulate my senses. After a short but memorable trip to Colorado’s Grand County a few months back I decided I wanted to spend more time in the state. The plan: use Airbnb to both sublet my place and get an apartment for a month in Denver.

This would also give me a chance to use my 2009 Honda Civic, which I loved dearly but didn’t have much use for living in NYC. The idea of driving through different states singing my favorite songs (ps. if they ever decide to reprise Rent I’ve now logged 30 hours of rehearsal time), enjoying the scenery and just spending some quality time with myself made me ecstatic.

I figured I could realistically drive up to 10 hours per leg, although I’d likely want a day or two in between drives.

My itinerary: Detroit, Michigan -> Des Moines, Iowa -> Denver, Colorado.

solo road trip

My road trip route

A Solo Road Trip On A Budget

I didn’t want to spend a ton of money on the drive, so I made sure to pack a ton of snacks and small meals: oatmeal, nuts, pretzels, cans of soup, bread, peanut butter, honey, Cliff Bars and a refillable water bottle were all part of my cheap eats arsenal, as were a few 5-hour energy shots. I know, I know, they’re awful for you; however, they’re one of the few drinks that actually give me lasting energy. When it begins to wear off I’ll usually grab a soda or coffee and something spicy to perk myself back up. I’m not sure if it’s in my mind, but Hot Fries were my savior when I started feeling the White Line Fever.

I also made use of Couchsurfing, which allowed me to meet and go out with cool local hosts (including an American Horror Story producer!) and get free couch accommodation.

Making Friends

My goal for the trip was to really immerse myself in Denver. I’d been to Colorado numerous times for the hiking and outdoor adventures (downhill mountain biking, anyone?), and while I wanted to do a little bit of that I more wanted to feel what it might be like to be a Denver local: picnics in the park, comedy and theater shows, bar events, booze brunch, art walks, cycling to get around.

While I’m fine on my own, being a local would mean I would need to find some local friends, of which I didn’t really have any before leaving New York. Thank goodness for technology.

solo road trip

My Airbnb and Airbnb friends

First step: secure an Airbnb. The most important feature would be the location. I wanted to be near downtown, where all the action was happening and B-Cycle bike sharing stations abounded. While the place I chose was slightly more removed than I wanted it to be, it was one block from the light rail, which got me to the downtown Union Station in about 10 minutes.

What was absolutely amazing about the Airbnb was it was more like a share house, with up to seven renters at a time. While for some this might sound like a nightmare, for a solo traveler it was awesome. I loved having people to hangout with, and when I came home at night I’d always find the guys — yes, it was me and four guys — hanging out on the couch with beer, bud and pizza. It was a seriously fun and relaxed vibe with positive energy.

I also did a bit of friend finding before leaving New York. Meetup.com was my first stop. As a solo traveler this is one of my top resources I use almost every trip. I perused the groups, searching by interest as well as poking around at how old the active members were. I found a few interesting groups and events, including two that ended up being particularly welcoming; a group of “not so girly” women who planned everything from yoga sessions to erotic bingo to potluck dinners, as well as a fun-loving Young & Social in Denver group.

solo road trip

Brunch at Argyll Whisky Beer with a new Meetup.com friend in Denver. Photo courtesy of Jessica Festa.

With each meetup I met more people, including many who had just moved to town. Moreover, whenever I saw people with profiles or postings saying they were new in town I’d private message them my cell and ask if they wanted to explore. Be proactive and you will meet people!

My third tactic for securing friends, although of a different nature, was dating apps like OkCupid and Tinder. The important thing when using apps like these for travel is to be completely upfront about your intentions. In my experience you can usually tell before meeting if the person is missing some marbles or just wants sex; but just in case be clear about what you’re looking to get out of the exchange. For me I was interested in dating with some romantic possibilities, but also wasn’t looking to be someone’s newest belt notch (the fact you’re only in town for a short while will be a plus to those looking for one night stands).

solo road trip

Unedited shot taken by me just as I entered Colorado. Photo courtesy of Jessica Festa.

One of the guys in my Airbnb was also the developer of an app called High There, sort of Tinder for marijuana users. While I’m not really a smoker I downloaded it to be supportive, and surprisingly (or not, this is Colorado after all!) there was a very active community in Denver — I met a slew of people on there! Not sure how active the users would be elsewhere, but it might be worth a shot, especially if you’re into THC products (though you don’t necessarily have to be).

Of course, social media goes a long way as well. Posts on my Facebook, Twitter and Instagram about the trip helped me connect with my readers and old friends, some of whom I even met up with, including a girl I’d traveled through Albuquerque with two years prior.

solo road trip

Brunch at Black Eye Coffee in Denver. Photo courtesy of Jessica Festa.

Immersing Myself In Denver

This was my longest solo road trip, and while the long stretches of driving were taxing at times I have to say I felt incredible freedom. The friendliness of the Midwest was infectious, and I’m not exaggerating when I say within two days I felt like I had true friends in Denver. Joining a gym, having a grocery store and favorite coffee shop, and even dating someone regularly helped cement this feeling.

So what were some of my favorite experiences in Denver as a solo traveler? While I could go on forever, here were some major highlights:

solo road trip

Photo courtesy of Williams & Graham

1. Creative Craft Cocktails at Williams & Graham. I was taken here on a date, and I was extremely impressed. Named the Best Bar in America at the 2015 Tales of the Cocktail, you enter a “book shop” where a shelf opens into a moody speakeasy, delicious plates of fois gras and croquettes pairing with creative cocktails crafted with atypical tinctures and infusions, high quality spirits, classic bitters and hand-cut ice in beautiful glassware. The bartenders are uber friendly, so even if you go alone you’ll have a great time and get a cocktail education.

solo road trip

Photo courtesy of Jessica Festa.

2. Cycling Around Town. As I wasn’t directly in downtown I had to make use of public transportation (and the occasional car service; tip: Lyft is your cheapest bet, and if you’re a new user can use code JESSIE299142 for $20 off your first ride). I would often take the train to Union Station in downtown and grab a B-Cycle from there, getting lost in the local parks and neighborhoods. You can download the B-Cycle app to locate nearby stations to check in the bike, which you should do every 30 minutes to avoid paying the $5-per-30-minutes fine. Otherwise, it’s $9 per day.

solo road trip

Native Roots goodies

3. Exploring Local Dispensary Culture. As stated above I’m not a big pot smoker; however, I was intrigued by the idea that you could walk into a shop and literally buy pot and THC edibles over the counter legally. While I was nervous it would be seedy or pretentious (I know almost nothing about smoking weed), it was actually like visiting a friendly wine bar, at least at Native Roots near my Airbnb. The place was squeaky clean, with walls adorned with marijuana-inspired drawings (such as seen on the bag above) and translucent cases of paraphernalia manned by knowledgeable “bud tenders.” Shopping for pot is akin to shopping for wine in the sense there are different varieties with different profiles and percentages (although in this case it’s THC instead of alcohol). If you’d rather have a snack, chocolate bars, mints, gummies and baked goods can fulfill your desires. Just be warned: eat with caution, they can be delicious yet potent.

solo road trip

Scenes from a Mount Falcon hike

4. Hiking Mount Falcon. While Colorado offers great opportunities to summit fourteeners, if you’re alone it may be a better idea to do something more populated and/or mild. One scenic option: Mount Falcon. When I hiked this trail on a random weekday afternoon I saw other hikers, and the trails are really well labeled. For something leisurely the Turkey Trot is pretty easy, while the Castle Trail is slightly more challenging and takes you to castle ruins, and you can do the Walkers Dream, too, the highlight shown in the center photo above. I’d recommend using DayHikesNearDenver.com for hiking inspiration.


Tattered Cover Book Store. Photo courtesy of Jessica Festa.

5. Getting nostalgic with literature. Denver is home to one of the greatest book shops I’ve ever come across in my travels: Tattered Cover Book Store. The space has an old, worn feel — sort of like your favorite book — with weathered wood, shabby leather chairs and a slight must, with plenty of common spaces, free Wi-Fi and even a separate study-like room for history and travel books. Grab some Vail Mountain Roasters coffee, single origin chocolate, Colorado Nut Co snacks or a decadent pastry from their cafe and dive into staff pick’s, bargain books, classics, indie titles, and an impressive assortment from a variety of niches.


Photo courtesy of The 1up

6. Games at The 1up. With two locations in Denver (in the LoDo and North Capitol Hill) this arcade-meets-bar-meets-concert venue is a great place to show up solo and challenge new friends to Pacman, skeeball, Joust and any of the other classic and modern arcade games. They’ve got 45+ games, 16 pinball machines, three lanes of Skee-Ball and multiple Giant Jenga sets — and an expansive local beer selection, not to mention live music almost every night. Don’t miss their vintage can collection, a whimsical brew experience.

Have notes on a solo road trip to add? Please share in the comments below. 


Road Trip USA: Cross-Country Adventures on America’s Two-Lane Highways by Jamie Jensen [Must Reads]

Clever Travel Companion Pickpocket-Proof Garments [Travel Safety]

Food Travel: 12 Accommodations Offering Immersive Culinary Classes [Blog Inspiration]

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  1. Amanda | Chasing My Sunshine on December 15, 2015 at 2:11 pm

    What a perfect post! I’m using my Spring break to head to Denver and try to live as much like a local as possible. These are some excellent suggestions, thanks! Actually, this whole style of travel sounds awesome. Now I just need to get an apartment I can rent out on AirBnB. 😉 If you had to do this again, which city would you stay in?

    • Jessie Festa on December 16, 2015 at 1:16 am

      @Amanda: Do you need an Airbnb in Denver to stay in? I really liked mine, though like I said it was slightly removed from the downtown (though very close by the adjacent rail). I’d honestly probably do Denver again OR I’d go farther and re-visit Portland, Oregon! 🙂

      • Amanda | Chasing My Sunshine on December 17, 2015 at 5:01 pm

        Luckily my friend’s family lives out there and they are offering me a place to stay. 🙂 But if I hear of anyone traveling that way, I will send them your direction! I think Portland would also be really fun to stay for a month. You’ve got excellent taste!!

        • Jessie Festa on December 17, 2015 at 6:17 pm

          @Amanda: Why thank you. You do, too! 🙂

  2. Erica Brooks on December 19, 2015 at 3:34 am

    I’ve always wanted to visit Denver. This post has definitely given me some good ideas. That brunch looks scrumptious.

    • Jessie Festa on December 19, 2015 at 6:54 pm

      @Erica: Oh it was delicious! 🙂

  3. April Yap on December 22, 2015 at 10:51 am

    I’ve been in Denver and I’ve always wanted to visit this place again and again simply beacause its beautiful and fun and on my next visit I have to try that cycling. 😀 Nice post!

    • Jessie Festa on December 22, 2015 at 6:05 pm

      @April: Thanks. It’s a great place! 🙂

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