History geek and reference librarian Derek Meader founded the Real Portland Tour in 2018.

During a recent media visit to Portland, Maine, I hopped aboard the Real Portland Tour. Owner Derek Meader guided a van-load of travel writers through the seacoast city he loves. For nearly two hours he regaled us non-stop with historic facts, intriguing oddities, personal anecdotes and groan-inducing puns. He even ends the journey with a rap song he wrote about his hometown. 

Here are a few tidbits:

* Portland burned to the ground 4 times, most recently on July 4, 1866.

* The Whoopie pie, a sandwich of chocolate cake and white frosting, is the official state treat.

* Maine has 3,500 miles of coastline, more than California.

* Portland’s harbor was attacked by Confederates during the Civil War.

* Portland hosts an annual ukulele festival.

After our morning tour, I coaxed Derek into a chat about his career as a tour guide in his hometown. Here’s an edited transcript.

Q: You were born and raised in Portland. What did you do after high school?

I went to Northeastern University in Boston. I ended up with a sociology degree, but I went there for baseball. I hoped to play professional baseball, but I had some injuries. I had a bunch of friends who were living in Washington, DC, so I moved there. I decided I was interested in research, so I went to grad school and got a master’s degree in library science. I worked in a couple of federal libraries and took classes at the Library of Congress. 

Q: After you received your graduate degree, you returned to Portland. Why did you come back?

A: I always knew I’d come back. It’s my hometown, and I love it here. I kind of lucked out. I started working for Maine Duck Tours during the tourist season, which is basically May through September. I also got a job as a reference librarian at Southern Maine Community College, which I still have, and the contract there is for the fall and spring semesters. I could research all the local history in the library. Once classes were done the first week in May, I transitioned to giving duck tours. 

I used to say I was going from stackin’ to quackin’, or from quackin’ to stackin’. 

Q: How did Real Portland Tour come about?

A: I got quacked out. I was doing so many duck tours, I decided in 2018 to start my own company. It’s a one-man company, just myself. On busy days when cruise ships come in, I have two volunteers–my mom and dad. For the annual company banquet, I take them out to dinner.

I call it the Real Portland Tour because I’m a real local. I’m the only born-and-raised Portlander who gives tours of Portland. 

Also, we are the real original Portland. (Note from PMcK: This is where Derek segues into the story of how Portland, Oregon, was named after Portland, Maine, in 1845 coin flip between two surveyors. Portland, Maine, was founded much earlier, 1786. You can Google it.)

Those are the reasons I named my company the Real Portland Tour.

Q: What do you love about Portland?

A: There is so much interesting stuff people don’t realize about Portland, Maine, and there’s so much rich history here. I just love telling people about it. When they take my tour, they can really tell I’m proud of where I’m from. 

Portland is obviously a smaller city. The population is just 67,000. The  peninsula itself is just three miles long, so it’s a very walkable city. We have all the major offerings you will find in a bigger city, just on a smaller, more livable scale. All the great restaurants, breweries, theater, ocean, beaches are right here. Then when you get out of the city a ways, there’s mountains and nature and lots of places to explore. You get the best of everything. 

Q: During the tourist season, what is your schedule like?

A: Typically, I’ll give three or four tours a day, seven days a week, May through October. My Ford Transit van has 14 captain seats and a high roof. It’s very comfortable. I find 14 is a perfect number. I can give a more personalized, in-depth tour and get deeper into history. Tours last about 90 minutes.

Q: Portland is a big foodie town. What do you recommend visitors eat when they come to town?

A: Everybody always asks about lobster, which you’ve got to try when you’re here. But there are so many different cuisines here. That’s why Bon Appetit named us the Restaurant City of the Year in 2018. The last three cities were Washington, DC, San Francisco and Chicago. When you compare the populations of those cities, it’s a pretty big distinction for us. 

You can do high end or casual, and all the food is fresh and great.

Q: You have traveled extensively through the U.S. What is the one essential item you don’t leave home without?

A: A good music mix. I do a lot of Stevie Wonder. He’s one of my favorites. I’ve seen him in concert nine times. Beyond that, I do like classic rock, too.

Book your Real Portland Tour. 

(Many thanks to Visit Portland Maine for arranging my Real Portland Tour!)