Need suggestions of scenic day rides/B&B's within 2-3 hrs of Chicago for September

The wife and I are celebrating five years of wedded bliss this September, and I'd love to go for a moderate day ride (~50 - 80 miles) and end up at a B&B for a romantic evening of showering and collapsing at 8pm.

We live in Evanston and I'd like to drive 2-3 hours at most. We ride road bikes, and I'd like to stay on paved roads or paths. Wine drinkers, food consumers, lovers of beauty.

Any and all advice and suggestions are welcome.

Thanks!

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I rode to the Indiana Dunes and was completely blown away by how beautiful that area is. I've always seen it from a car. Bike Paths make up the majority of the ride and what little street riding you'll have is quiet and easy going.The bonus is that the paths and roads are already marked by the Tour de Shore...so you just follow the markings.

Mineral Point, WI. would be my first choice for an anniversary weekend.

Stay at the Brewery Creek Inn. A very romantic 5-room hotel, located in a building dating back to 1854. Lots of quiet back roads (hilly) and limestone paths (flat) starting right out outside the front door. Not sure about wine options, but the Inn has it's own brewery (hence the name) and makes some very decent beers. Also has a very great food menu, focused on locally sourced food. The restaurant is closed on Sunday evenings.

Lots of art shops in town and it has a lot more small town feel than for example Galena, which can be overrun by tourists.

On Sunday, take a tour at Pendarvis, the local historic site. Definitely worth the hour or so it takes

I think it is about 3 hours driving.

+1, I really liked this B&B, they have a bike theme and all.  There's lots of great riding all around there, you can do the rail to trail path one day and ride around the kettles the other.  

The owner is really nice, and set us up with a special picnic basket since they had a candlelight ski night & grilling at the state park that weekend.  Breakfast was amazing, and she carefully accommodated my allergies.  The bedding was very comfortable (many of my fav. B&Bs have had terrible beds) and the room was very nice.  We had bedchamber 4, which was perfect for soaking in the tub and warming by the fireplace after hours of cold (yet with little snow) xc skiing. 


Cameron Puetz said:

The Pedal'rs Inn in Wales, WI is bike themed and in the middle of the Kettle Moraine area which has some great riding. Liz and I stayed there in February for a cross country ski weekend and have considered going back for a bike weekend.

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