One of the luxuries of living in Chicago is being able to travel by train.  I’ve always thought it would be fun to take my bike on the train and explore a city on two wheels. So, last weekend my girlfriend and I packed our backpacks and pedaled down to Chicago's Union Station to embark on a 5-hour journey to the Gateway to the West.


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Jake Bartlett

Our train arrived downtown St. Louis Friday night, about a mile from the Holiday Inn we’d booked for two nights.  After a quick bike ride to the hotel, we were greeted by friendly staff in the lobby, which was appropriately decorated with inspiring photography of the city.  We had our eye set on enjoying St. Louis’s famous toasted ravioli, which is really a breaded, deep-fried appetizer.  We honed in on a quirky cocktail lounge/bowling alley on Washington Ave. with the promise to taste this notorious snack.


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Jake Bartlett

The next morning we started our day of biking the right way: with a hearty breakfast and a Bloody Mary. We wound up at Rooster which was within riding distance from the Holiday Inn. This popular breakfast joint is a part of an eclectic restaurant group called Bailey’s Restaurants family that each focus on a unique culinary genre.

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Jake Bartlett
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Jake Bartlett

Our first tourist stop was of course, the Gateway Arch.  No good adventure goes without a roadblock though… literally.  Unfortunately the entire area around the monument was closed off due to a large construction project in the park surrounding the arch, so we couldn’t get as close as we wanted.  

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Jake Bartlett

We pressed on to the Missouri Botanical Gardens, an 80-acre oasis of plants, ponds, and fascinating history. The highlight there was taking a self-guided tour of Henry Shaw’s mansion. Shaw was a St. Louis philanthropist who founded the garden and donated the land for Tower Grove Park, surrounding the estate.


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Jake Bartlett

From the gardens we headed north to a vibrant little pocket of the city called The Grove. Fittingly, we parked our bikes at Handle Bar, a bike-friendly bar and restaurant that delighted us with a small discount for having our bike helmets with us!  

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Jake Bartlett

After indulging in a well-earned cold beer and St. Louis-style pizza, we pedaled west to the city’s largest green space: Forest Park. This place was beautiful and enormous. Having ridden around 20 miles, we were ready to freshen up and find a relaxing spot for dinner so we returned to the Holiday Inn, forgoing the paddleboat rental that beckoned in Post-Dispatch Lake.

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Jake Bartlett
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Jake Bartlett

Leaving our two wheels behind, we made our way on foot to the Bridge Tap House & Wine Bar. It was here that we met David Bailey, the brains behind Bailey’s Restaurants family.  He helped us pair our cheese and charcuterie board with wine.  That’s right, dinner consisted of a bottle of wine and cheese. No regrets.

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Jake Bartlett

Thanks to the accommodating hotel staff, we arranged a late checkout and hopped back on our bikes for a post-breakfast ride. This time we set out along the Mighty Mississippi via the Riverfront Trail. The trail, which winds along the Mississippi passing through junkyards, floodwalls, and other industrial sites, was an awesome contrast to our urban ride the previous day.

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Jake Bartlett

After about three miles of riding, we were intrigued by some signage for the Mary Meachum Freedom Crossing and Rest Area, and decided to pause to scope it out.  What we learned was shocking and rather ironic.  In 1855, a free black woman named Mary Meachum attempted to guide a small group of slaves to freedom across the river to Illinois.  Police caught them on the other side, locking Mary Meachum behind bars.  Most of these stories have gone undocumented, but this one received special attention from newspapers because – and here’s the irony – the slaves belonged to Henry Shaw, the wealthy philanthropist whose mansion we toured the day before. Our St. Louis trip had gone full circle and we realized the importance this area has on our country’s history.  


We returned to the city for some mandatory last stops before our train ride back to Chicago. First, burgers and boozy milkshakes at Baileys' Range - our 3rd Bailey establishment.  The Irish coffee shake was a superb way to cool off after our bike ride!

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Jake Bartlett

We’d also conserved some energy to explore the City Museum. At eleven stories high, the part funhouse, part architectural/industrial design museum, and part natural history museum was a funky and fascinating place.  They have an entire room dedicated to the design of door knobs and yet another to host insects and taxidermy! Kids love this place because of the massive jungle gym/fun house features. We made sure to partake in this ourselves, including the 10-story slide.

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Jake Bartlett

We finished off the trip by validating St. Louis’ booming craft beer scene at Alpha Brewing.  We even had a chat with the two brothers who own and operate the facility and left with a full growler of their summertime brew dubbed, Ginger Wit.


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Jake Bartlett

Before this trip, I wasn’t sure what St. Louis had to offer.  In fact, some of my friends asked “Why are you going there?”.  Sure, the city has seen its troubles, but it proved to be a city packed full of culture, architecture, and history.  I feel we only scratched the surface during our visit, and I look forward to returning to see more of this iconic city.

By: Jake Bartlett

A self-proclaimed “adventurer”, Jake Bartlett loves to travel.  In the last 3 years he’s visited 7 countries, backpacked several locations in the states, and ceaselessly explored his home city, Chicago.  A drummer and bike commuter, he enjoys hosting other travelers and dropping local knowledge on the city. Check out his blog backpackchicago.com, a simple guide for exploring and visiting Chicago.