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Ask a Local: Dale Jacobson Co-owner of Skyway Drive-In Theatre


Skyway Drive-In Theatre is a place for families to gather, whether that means settling in with a big bucket of popcorn or, in Dale Jacobson’s case, owning and operating Wisconsin’s longest continuously running drive-in theater with his brother, Jeffrey. They take care of the theater’s day-to-day operations — May through October — but you’ll often see their mother behind the ticket window; she ran the place with her husband until the boys took over in 1999. Dale’s niece works at the snack bar, and his aunt also sometimes sells tickets. Fun fact: The theater was originally owned by two brothers.

Today, you can catch a double feature and park next to traditional speakers installed nearly 75 years ago; even the pre-movie ads include commercials made in the 50s. There’s a snack bar serving locally made apple cider and ice cream, a playground, and, inclusive of the whole family, a dog-friendly atmosphere.

Q. The double features end pretty late. What are some of your favorite coffee shops to hit in the morning?
A. I like Kick Ash for its bakery items and open, airy space. Blue Horse Beach Cafe has good coffee; sometimes I go there for lunch, too. Sip has done a nice job with remodeling their space, and along with coffee they sell home decor.

Q. Where do you go for breakfast?
A.  Al Johnson’s Swedish Restaurant for the Swedish pancakes, of course, and Good Eggs by the beach in Ephraim for breakfast burritos. 

Q. Where do you go for a sweet treat?
A. Ice cream from Wilson’s or Door County Ice Cream Factory, especially the coffee flavors or maple-nut.

Q. Where do you go for a special night out?
A.  The Nightingale Supper Club. It’s an old-school supper club; I get the steak.

Q. What do you do on your time off?
A. I take the ferry with friends for a daytrip to Washington Island. 

Q. Where do you go to enjoy nature?
A. Peninsula State Park has great trails to walk and run. Anderson Dock is a unique place to relax by the water.

Q. What is your can’t-miss Door County event?
A. I see a lot of old friends and classmates at Sister Bay’s Fall Festival. It’s a big homecoming gathering, where streets are closed and vendors set up booths.

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