It isn’t hard to come up with an excuse to take off on a road trip, even if it is just a short overnight adventure.

My road trips tend to focus on things I enjoy, like hiking, camping and nature. I also like baseball, so the idea of taking off to Cleveland, Detroit or Pittsburgh for a weekend drive from Toronto is pretty common.

Sometimes a short road trip has a way of turning into a big one though. After I convinced a buddy to come along, the baseball weekend trip turned into a week-long 3000 km / 2000 mile adventure! And so, the week-long Great American Baseball Road Trip began…

 

We had it planned perfectly to catch 7 baseball games in 7 different parks over 8 days.

Seriously proud of our logistics, the excitement of the road trip had us buzzing as we left Toronto at 3am for the 10 hour drive to Boston.

About those logistics – seeing so many games in so few days ins’t easy. The biggest tip on getting the most out of a baseball road trip? Start your trip on a Monday or Thursday. Those are commonly ‘getaway’ days you can squeeze in an extra afternoon game, or catch an extra team at their first / last home game instead of chasing them half way across the US.

Baseball Road Trip Stop 1: Boston

 

Fenway Park! As baseball fans, seeing a game in Boston is a dream. We snagged some crappy ‘standing room only’ tickets and had fun walking around the park, staring at the Green Monster and watching our team, the Toronto Blue Jays, beat the Boston Red Sox!

We kept our cheering to a minimum though, as there were some unfriendly looking locals surrounding us. As fun as that was, the time outside of the park was even better. Walking along Yawkey Way and taking in the street party scene before the game was a real treat. Today, Fenway Park remains my favourite MLB park to visit.

Baseball Road Trip Stop 2: New York City

 

Since we had two nights here, long enough to catch a Yankees and Mets game, we decided to stay at a hole-in-the-wall hotel just off Broadway and close to Times Square.

Unless they’re playing each other in inter-league play, having both the Mets and Yankees at home on the same weekend is pretty rare, so we were excited. But, the allure of the bright lights of the Big Apple got the best of us and our 7 games in 8 days turned into 6 games in 8 days + a David Letterman Show.

The ubiquitous guy on the street offered us tickets to a Letterman taping. The catch was we’d have to miss our Yankees game. My buddy was a huge Letterman fan, so the decision was made. It was a fun show, lots of laughs…and it also let us enjoy more eating and drinking time in Manhattan!

The Mets game the next day was a real treat too, a perfect sunny summer day, seemingly created for drinking beers and watching baseball. After our two days in NYC, we were off to the city of not-so-brotherly love.

Road Trip Stop 3: Philadelphia

 

Let’s get the hell out of here! That was our unanimous feeling about Philadelphia. Sorry Philly fans, but your city definitely wins the worst baseball road trip experience award.

Things were all good getting to Philadelphia, but once we got off the freeway and headed downtown, there was a creepy vibe. Maybe it was the guy who tried to get into our car while we were driving? Or the other one who yelled obscenities at us for no known reason when we stopped at a red light.

We didn’t even feel welcomed at the gas station, which conveniently featured bullet-proof glass windows for the safety of their workers.

As for the baseball game, we had atrocious nose-bleed seats. The only decent thing was we could say we had a Philly cheese steak sandwich.

Without a hotel booked, we shuddered at the thought of leaving the safety of the ballpark at night, Philadelphia was scary enough during the day! So we decided to pull an all-night drive to Pittsburgh!

A late-night fast-food stop kept us awake long enough to roll into Pittsburgh just in time for sunrise.

Road Trip Stop 4: Pittsburgh

 

Talk about night and day. As much as Philly sucked, Pittsburgh rocked. First, the random hotel we ended up at let us check-in at 8am. Nap time!

A few hours later we were drinking beers at the hotel bar, thinking about what to eat. We wanted steak and the kind bartender told us about the Outback Steakhouse at PNC Park. Sold! With that, we performed some more ticket trickery by watching the start of the game from the Outback Steakhouse located in left field.

Afterwards we had free reign to wander around the ball park. If Fenway was a favourite for nostalgia, then PNC Park quickly became a favourite for location and setting. With a river in the background and sun setting off of downtown Pittsburgh and the Roberto Clemente Bridge, it was a perfect night of baseball. The scary memories of Philadelphia quickly faded away.

 

We loved Pittsburgh so much, that we shut the city down. Literally closing two bars and having to walk to our hotel as taxis seemed to be non-existent late at night.

Road Trip Stop 5: Cincinnatti

The festivities of the night before meant next to no time in Cincy. We arrived just in time to catch a game and drive to Colombus for the night.

It was really just a blur of a day, but as neither of us could think of any other reason to ever return to Cincinnati, we went anyway.

Road Trip Stop 6: Cleveland

 

It was a busy weekend in Cleveland, which caught us off guard. We arrived early, but every hotel we checked was booked solid. Crap.

That gave us some time to explore the city and get to the ball park right when gates opened. Progressive Field had a nice, natural feel to it, with a great beer garden in the outfield and good variety of food options scattered around.

It was quite a contrast to the cramped confines and concourse areas at Fenway Park! Spacious and bright, we didn’t care that the Indians were playing horrible at the time, as we actually enjoyed the ball park itself.

As our last game of the road trip came to a close we had to decide what to do next. Keep trying to find an overpriced room in Cleveland or drive on to somewhere else?

We drove on, to some rural area in Ohio. A random town with two motels and a restaurant/bar. All we needed!

Celebrating our road trip with pitchers of beer and pounds of wings, we both agreed we’d have to do another baseball road trip one day – to the west coast.