Where to next?
May 27, 2022 7:10 AM   Subscribe

Mr. DrGail and I (and our dog) would like to go someplace within about a day's drive of Chicago at the end of August through Labor Day weekend. I would love some help figuring out where that ought to be. Details inside.

We plan on renting a vrbo and love being able to walk to restaurants for a drink and a meal, visit funky shops and art galleries, and so forth. Maybe sit on a front porch and chat with neighbors and passersby. A dog-friendly area/city is a must. For example, the suggestion of Eureka Springs in response to this question was right on the money - we loved it there. What towns, or neighborhoods of cities, would you recommend for us? And are there any must-visit places there or nearby we shouldn't miss?
posted by DrGail to Travel & Transportation (8 answers total) 6 users marked this as a favorite
Have not lived in Chicago for about a score of years, but going to Lake Geneva Wi was always a good time. Laid back, nice town, lots of recreation in the area, etc.
posted by JohnnyGunn at 7:27 AM on May 27, 2022

Madison might be obvious, but it fits the bill pretty well. There's also Lake Geneva, perhaps with the exception of art galleries. (There is an arts scene, sorta - but exciting fine arts would be a special event.) [edit: JohnnyGunn beat me to it. Cheers!]
posted by eotvos at 7:29 AM on May 27, 2022 [2 favorites]

Wow, a day's drive from Chicago gives you a ton of options. I'm from Ohio, so that's my first thought. Yellow Springs is about 5-6 hours by car, and it's got exactly what you're looking for in terms of restaurants, walkability, and funkiness. Maybe even more funkiness than you knew you wanted! I've never been to Eureka Springs, but I see it on the same kinds of lists of "funky towns" as YS, so I think YS would be good for you. Best hiking in Ohio, if you're into that. The only downside is I'm not sure about VRBO availability. It's a pretty small place.

For a bigger city, the part of Columbus just north of downtown would work: the Short North, Victorian Village, and the Arena District. The Short North is (or was, thanks gentrification) the artsy neighborhood. Victorian Village is residential and would probably have some nice VRBOs. It's all walkable, and there are some really good restaurants and a nice park (Goodale Park).

In St. Louis, you could have a fun time around Forest Park. I think the Central West End would probably be the easiest place both in terms of finding a VRBO and walking to a variety of places. I used to live in the Delmar Loop, and that's probably the funkiest neighborhood in STL, but it's smallish and there's a lot of student housing, so maybe harder to find the kind of place you're looking for. Either way, Forest Park is incredible and should be a focus of your visit. Your dog will love it.

The west coast of Michigan is pretty nice. I've been to Traverse City and Manistee, and both are pretty charming. Friends have great things to say about Grand Haven. And Grand Rapids, as a city, is a fun town too. Especially if you like beer. The southeast part of the city, around Wealthy Street, is probably what you're looking for.

Any of those would be fun trips, but you're gonna get a lot of other good suggestions too. There are a lot of fun places in that part of the country.
posted by kevinbelt at 7:35 AM on May 27, 2022 [1 favorite]

Kansas City is an 8 hour drive from Chicago, full of fountains, museums, and tasty BBQ. You can take your dog on the Southwest Chief, if you prefer to travel by train.
posted by olopua at 7:41 AM on May 27, 2022

Might be biased as I live here but Winona MN is a pretty chill town in the driftless region of the Midwest so it's bluffs and valleys all along the Mississippi. Small town vibes, easily walkable, generally dog friendly, good hiking and tons of bars and little shops.
posted by Ferreous at 7:54 AM on May 27, 2022 [3 favorites]

The City Museum in St. Louis is unlike anything else and absolutely worth the not-too-long trip from Chicago. Added to the other great suggestions you've gotten for STL, it would make a very nice getaway.

I'm grew up Grand Rapids, MI, which has gotten a lot cooler since I moved away. If you do a Michigan trip, I'd highly recommend staying in Saugatuck or Douglas (adorable small towns, great good and art galleries, Oval Beach) and doing GR as a day trip to catch Meijer Gardens, Max's Tiki Bar, and lots of breweries.
posted by dapati at 7:59 AM on May 27, 2022

Seconding Winona, so pretty!
posted by Lawn Beaver at 8:34 AM on May 27, 2022

And if you go to Winona, I recommend a drive over to Trempealeau. It's a tiny town on the Mississippi that doesn't look like much, but the old hotel there is a good spot for drinks and dinner.
posted by TrialByMedia at 5:58 PM on May 27, 2022

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