The Date Day Diary

Chicago Area Date Day Ideas

Our first Date Day was September 2, 2015.  We went to Michigan City, explored antique stores, had a nice lunch and started our adventure.  Today, we marked 139 weeks in a row by going to Crown Point, IN and doing the same thing.  Believe it or not, sometimes it’s hard to have a Date Day every week.  We get tired, we get sick or we just want to sleep in.  Today was one of those days, but we persevered and ended up having a good day, and the best (and much needed) conversation we’ve had in while.

Crown Point is a great little city in northwest Indiana.  Its downtown square is filled with quirky shops, antique stores and restaurants.  In the center of the square is the old Lake Country Courthouse.  A picturesque building, designed in 1878 and featuring a combination of architectural styles.  The courthouse is famous for being the “escape proof” jail from which John Dillinger escaped in 1934.  Adding insult to injury, Dillinger stole the sheriff’s brand-new Ford during his escape.  Today, the courthouse building is open to the public and houses shops and the Lake County Historical Society Museum.

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We spent a pleasant few hours wandering around the square, ducking in and out of the shops.  We saw lots of interesting items, but only bought a single pillow.  When we got hungry, we chose Tavern on Main, out of many good option.  We had a nice lunch of Crispy Cauliflower, Roasted Beet Salad and Margherita Flatbread.  The salad and flatbread were good, but the cauliflower was out of this world.

If you ever want to spend a lazy day in a friendly little town, Crown Point is a place to check out.  The shops are great, the square is beautiful, and the place just has a good vibe.

As for the conversation, we’ve been agonizing over buying our next (retirement) home for well over a year now.  We’ve made offers on two houses, only to have the deals fall apart before closing.  We’ve also had some pretty good arguments about what we are looking for.  Today, we realized the same thing we realized 18 years ago when we built our current home.  Ours hearts are not in buying someone else’s house.  We want to create something special for ourselves and our family.  Thus, the next adventure begins …

April 2018
Crown Point, IN
2 – 3 Hours
Free Parking
Tavern on Main
136 S Main St. Crown Point IN
$50 Including drinks and tip
1 Hour
Free Parking

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