The 3rd Annual Briggs City-A-Year Trip: Pittsburgh


For the past three years, my dad, brother and I have participated in the Briggs City-A-Year trip. It’s quickly become one of our favorite traditions. Since my parents live in Phoenix, my brother and his family live in Colorado and I live in the Philadelphia area, we don’t get much quality time together in a calendar year. So we’re a bit purposeful about our time together.

With City-A-Year we carve our three days during the third week of August.

We pick a “B level” city somewhere in the country (e.g. San Antonio, Minneapolis, Milwaukee, Memphis, Salt Lake City, Kansas City, St. Louis, etc).

And because of our love of the great game of baseball, the city must have a major or minor league baseball team that’s playing at home during our trip.

PNC Park

We explore the cultural elements of the city in various forms (bike, Segway, canoe, the Metro, kayak, cable car, etc). We have lingering talks in local coffee shops, uninterrupted conversations in cool diners and lengthy discussions in our hotel room.

We eat at local eateries and hole-in-the-wall joints.


We do research on the city (watch a documentary or read a book about its history) ahead of time.

We try to make lasting memories while doing all we can to avoid the “touristy” things. We try to get the real experience, doing our research ahead of time to get the insider’s scoop on the place.

Three years ago was Indianapolis. Last year was Charleston, SC. And this year was Pittsburgh.

Kayaking PGH

We saw the Pirates win in dramatic walk-off fashion against the Braves at PNC Park (which ties for my favorite ballpark in the country).

We ate the most amazing hotcakes at Pamela’s, explored the Strip District, visited an old decommissioned Catholic church that has been turned into an incredible brewery, did some urban kayaking through the three rivers right past the high rise buildings downtown and under the bridges and ate a very “unique” sandwich at Primanti Brothers.

We biked for at least 20 miles along the river fronts and around the city.


We even drove two hours to Cleveland to watch the Indians play the Astros at Progressive Field. (Dollar Dog Night and post-game fireworks are a nice bonus).

We also narrowed down the list of the final three cities we will go for City-A-Year next year (Austin TX, Boise ID and Portland, ME).

Church Brew Works

Needless to say, we had a blast. And Pittsburgh was way cooler than we imagined.

If we want to see more of our adventures, check out the hashtag #briggscityayear on Instagram.

Mt Washington selfie

Tomorrow I’ll share about the most impactful half-day of our trip, a visit to a nearby town where 90% of its original buildings are in a landfill. The stalwart resolve of the community leaders was palpable, the sites we saw were sobering and the stories we heard were inspiring.