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Oh Sierra


Field Notes From A Cross-American Road Trip

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By Sandy Osojnik

As we packed the last bag into my sister’s two-door Jeep, and the Los Angeles sun started to slowly fade into the afternoon, we had the taste of excitement and anticipation for the 10-ish days ahead, making our way cross-country — destination Canada. 

With a final check for our passports, vaccination documents, and making sure that Goblin (my sister’s sweet-souled mutt) did indeed have enough space to snooze in the back seats that were mostly taken up by overstuffed suit-cases, coolers of snacks and refreshments and sentimental treasures waiting for family and friends across the border, we loaded up and headed out on a cross-country road trip back to our hometown of Toronto. 

With my sister Andy behind the wheel, and myself acting as the navigator, in-flight entertainment and appointed pooch-wrangler, we plotted out our route across 8 different states, staying with friends, and at boutique hotels along the way. Typically gravitating towards cool Airbnbs, we opted for the hotel option this time around, seeking easily accessible, centrally located properties, dog-friendly rooms, and of course, a breezy check-in and check-out procedure — all with the promise of a stiff cocktail at the hotel bar after a long day on the road. 


DAY 1: LA to Phoenix – where we would crash with a good pal offering us hospitality for the night, and the chance to play with their five dogs, my personal heaven tbh. Road Recco: Check out Valentine for their wicked caffeinated bevvies, freshly-baked goodies and stunning space before heading out. 

DAY 2: Phoenix to Santa Fe – where, again we would be invited into the beautiful family home of our friend’s parents, who also happened to be visiting at the time. For a no-fuss grab and go breakfast, try out the breakfast burritos at Blake’s Lotaburger or Tia Sophia’s. 

DAY 3: A day spent in Santa Fe exploring the town’s charming downtown plaza, eating, drinking, and hitting up the Georgia O’Keefe Museum. If you’re looking for a place to stay, check out the hip El Rey Court, a historic boutique hotel along the famous Route 66.

DAY 4: Santa Fe to Woody Creek: this small town neighbouring Aspen is perfectly picturesque, and home to a dear friend who generously took us in for the night. We were lucky enough to share a home-cooked meal and meet some pretty sweet rescued horses that were being boarded on the family property. 

This route took us through Colorado’s Independence Pass, a mountainous winding road, with breathtaking views, which is typically closed (and for good reasons) during the winter months. Stay the night, or enjoy a swanky breakfast in Aspen’s Hotel Jerome, a historic landmark offering modern luxury lodgings. 

DAY 5: Woody Creek to Denver: a place neither of us had ever visited, but seemed like a cool spot for a pit-stop. We booked a room at the cool, Goblin-friendly boutique hotel — the Source Hotel. Make sure to check out the on-site restaurant Safta for some delicious Israeli-inspired eats. Road Recco: Pop into Darklands for a morning coffee, and snag yourself some killer vintage pieces.

DAY 6: Took a day to explore Denver popping in for lunch at the Denver Central Market, and checking out local, independent retailers like the beautifully-curated Meek Vintage, and Conifer: a sustainable home goods and ceramics shop with a fluffy ginger cat that sleepily welcomes you as he naps in the window.

DAY 7: Denver to Kansas City: We didn’t really know what to expect from Missouri’s largest city, and we were pleasantly surprised by the warm welcome as we checked into the Crossroads Hotel, a modern, downtown hotel that once housed the Pabst Brewing Depot that is rumoured to have been a hotspot for bootleggers. For natural wine lovers looking for a good chat and some funky bottles, check out Big Mood Wine, located just a few blocks from the hotel. Kansas City really impressed us and we’re eager for a return trip to try out some of the city’s famous BBQ and pop into one of the many beer gardens for a bite.

DAY 8: Kansas City to Chicago: Before leaving Kansas City, grabbing a coffee and fresh pastry from Messenger Coffee + Ibis Bakery is a must. We ended up being fuelled by our bountiful box of pastries for the rest of the day – no regrets. After a manic drive into Chicago’s downtown during rush hour, checking in to the Ace Hotel and enjoying a burger and Negroni Bianco on the patio was a very welcomed treat.

DAY 9: A day spent in the Windy City included taking in the phenomenal Obama Portraits and Bisa Butler exhibits at the Art Institute of Chicago, an architecture tour along the river (yes, it was on a boat, and yes, there was booze), a fresh Italian-Croatian meal at the industrial-chic Rose Mary, and of course, calling it an early night and watching the classic Chicago-centric flick, Ferris Bueller’s Day Off, in bed. 

DAY 10: Chicago to Detroit: Stopping in Chicago’s suburb of Oak Park to check out Frank Lloyd Wright’s Home and Studio, we reached Detroit just in time for dinner and a nightcap. We settled into the Shinola Hotel — one of my personal faves when it comes to modern, boutique hotels that embody quality craftsmanship and style. Guests can relax and savour a cocktail in the living-room style grand entrance before heading to the hotel’s restaurant San Morello for some authentic wood-fired pizza and homemade pasta. 

DAY 11 + 12: Preparing to cross over to the border into Canada, we secured our COVID tests and patiently awaited our results. Having to stay one night more than expected, and needing a little more work space in our room, we moved to another Detroit hospitality stable, the Foundation Hotel — an old fire-hall that was re-imagined into a hotel, restaurant and event space. Ordering in some Chinese food and indulging in face masks was the perfect way to cap off almost two weeks on the road. 

Crossing the border on Day 13 was an unexpected breeze. We had planned our arrival to coincide with COVID quarantine restrictions being lifted for fully-vaxxed Canadians, and with minimal crowds and questioning at the border, we safely made our way to our final destination. 

So, some final reflections from the road, and driving cross-country in the times of COVID:

Have plenty of snacks, water (and caffeine) available to avoid frequent pit stops, and sibling quarrels.  

Don’t drive when you’re tired. It’s better to pull over, take a nap, or split up the drive between days. 

Know what health and safety regulations are in place everywhere and respect unique local guidelines when visiting a new city. Not sure what they are? Ask the front desk of your hotel, your host or do some diggin’ online. 

Leave some buffer room to receive COVID test results, and plan your testing accordingly. 

Most importantly, talk to local folks and get the inside scoop on where to eat, where to drink and what neighbourhoods to check out. So many of these awesome spots were suggested by friendly locals, neighbourhood bartenders, knowledgeable shopkeepers or just through casual conversation with strangers.

Travel as we used to know it has changed somewhat, but the spirit to explore, discover and learn remains as vibrant as ever. The electrifying buzz of driving into a new city, the feeling of clean sheets and a comfy bed after a long day on the road, the snippets of conversation overheard as you walk through bustling streets, or the feeling of genuine connection with a stranger who’s welcomed you with a familiar smile — now that’s the stuff.

Signing off from a pretty epic road trip, 


See the whole adventure through my “roadtrip” highlight on IG! Have any questions, or recos? Feel free to shoot me a DM 😉

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