Meet Captain Gregg Pupecki—Waukegan Harbor General Manager

Gregg Pupecki with George Bush Sr.

The New Waukegan Harbor Team

Captain Gregg Pupecki has been around boats all his life: as a child growing up on the New England coast; as a commercial boat captain; and as an executive with Chicago’s Wendella Boats. And today, Gregg is still around boats…and then some.

As the new General Manager for Lake County’s Waukegan Harbor, Gregg is responsible for day-to-day operations and planning for a harbor with a marina that has over 1,000 boat-slips. Recently, we talked with Gregg to learn more about him and his vision for growing Waukegan Harbor as a “must-go-to” destination…

Q: What’s your vision for Waukegan Harbor?

A: My vision for Waukegan Harbor is to solidify it as a “must-go-to” destination, both for people with boats all across the Great Lakes and for people without a boat. I want them to come down and be able to take a boat tour, hop on to a sunset cruise, take a water taxi, have an ice cream and stroll the HarborWauk.

Q: What are some things you’d like to accomplish in the near future?

A: One of the top things is to bring in a full-time food-and-beverage operator. Also, I want to create a way for the public to access the water and the excitement and fun that the water brings. Right now, if you don’t have a boat, there’s really no way to really experience the water here. You don’t have things like kayak rentals—which I’m looking at getting—or Ski-Doo or Waverunner rentals. You can hire a charter fishing boat to take you out fishing. But it’s little bit different than having a tour boat or water taxi type of service.

Q: Could you tell us a little about your background and what attracted you to Waukegan Harbor.

A: I was born in Massachusetts, and I grew up around boats all my life. We had a second home in Kennebunkport, Maine, and our boat was in the same marina in the 1980’s where then-Vice President George Bush docked his boat.

After studying business and marketing at New Hampshire College, I was working for NBC news in Chicago in 1996 when I discovered the Wendella Sightseeing Boats company. That’s where I started my professional career. I studied at New England Maritime, got my captain’s license and ran a boat for several years. And that’s how I got into the paid side of the boating business.

When the opportunity came up in Waukegan, I said to myself, “Well, this ties everything together: my commercial side, my marketing/sales side, my boating side. It seemed to be a perfect fit.”

Q: Can you describe briefly what your job in Waukegan Harbor entails?

A: As general manager, I’m responsible for the day-to-day operations, as well as overseeing implementation of future goals and projects. I work with different groups to develop a vision for the harbor. I’m also responsible for customer satisfaction, services, sales and marketing and community outreach. I help make sure that Waukegan Harbor is and will continue to be part of the community and a destination.

Q: What would be the number one thing you’d like the public to know about Waukegan Harbor?

A: Waukegan Harbor is currently a great place to come down to take a stroll, grab an ice cream from Dockside Ice Cream, check out the marina, or experience music at The Harbor’s Edge—and that’s just what’s currently going on now, which many people don’t realize.

Obviously, it’s a great place to keep your boat. And between live entertainment and amenities plus the full-service marina, it’s a great place to be. And in the future, it’s going to get even more exciting.

Q: How much support are you getting from the city for HarborWauk and other initiatives?

A: I have a really good working relationship with the city and mayor’s office. We all understand how development along the harbor is great for the whole community. The city has just finished the Grand Avenue entrance to the harbor. There’s a bike path, great sidewalks and lighting. That makes a huge difference.

And then we have the Bay Marine project—with a yacht sales, service and storage facility—that’s going to be built here. There will be  a lift well to get good-sized boats out of the water and also indoor heated storage.

Q: Do you own any watercrafts yourself right now?

A: That’s actually one thing I’m feeling withdrawals on, because it’s torture to be at a marina without a boat. As a captain, I’ve been used to driving other people’s boats. But I’m actually looking for a small, center-console boat.

For more information about Waukegan Harbor and things to do, visit

Next entry | Blog Index | Previous entry