Road trippin' out of Chicago?
August 28, 2007 2:40 PM   Subscribe

Road Trip filter: My girlfriend and I live in Chicago, and we want to take a road trip somewhere for the long weekend.

Please offer your suggestions for where to drive. We're not looking to spend a whole lot of money, and she grew up around here so I need suggestions that are little less obvious than "go to the Dells". Also, we would like to avoid the holiday traffic as much as possible.

Not really looking for kitschy tourist traps, and we love nature and beautiful scenery, but we weren't planning on camping. Two ideas we had were to just dive to the Twin Cities, or check out some of the vineyards in Michigan (if anyone can comment or give advice or experiences on either that would be awesome as well).

She has explicitly said that Indiana is not an option, but other than that I'm all ears! What are some of the Midwest's best kept secrets?
posted by AceRock to Travel & Transportation around Chicago, IL (28 answers total) 10 users marked this as a favorite
The problem with it being the last holiday before school starts is everything within a half-days drive of Chicago is going to be crawling with last-minute vacationers.

Maybe head west to Galena and follow the Mississippi north? Cruise up towards Eau Claire (flipping the bird at the Dells on the way past), tour the Leinenkugel brewery, and visit some state parks? Blast down to Missouri and explore the Ozarks?
posted by indyz at 2:48 PM on August 28, 2007

Trempealeau, Wisconsin, is a sleepy li'l town on the banks of the Mississippi, north of . Nearby attractions include some remarkable hiking, state-parking, wildlife-refuging and bicycling on some well done trails. The Trempealeau Hotel is where you'll want to stay. Enjoy.
posted by diastematic at 2:50 PM on August 28, 2007

... "North of La Crosse."
posted by diastematic at 2:51 PM on August 28, 2007

Here's a gorgeous day trip from Chicago I took back in '99. Madison is a fantastic town. Southwestern Wisconsin, along US151 toward Dubuque is gorgeous. Tooling around eastern Iowa is lots of fun, especially the small towns (I especially liked Belvedere) on the west bank of the Mississippi. Savanna, Iowa is on an island; everyone has a boat hitch. Then you get to drive through Illinois farmland, through Dixon, picking up I-88 midway through the state.
posted by Saucy Intruder at 2:56 PM on August 28, 2007

I'd like to suggest the Ozarks in Missouri (they are quite beautiful,and there are a lot of things you can do on the lake), but they might be very crowded this weekend. I guess most anywhere will be busy, though. Here's a link:
posted by emilyv at 3:02 PM on August 28, 2007

Have you looked at all the other posts tagged Roadtrip Chicago? This one might give you a few ideas.
posted by MsMolly at 3:03 PM on August 28, 2007

Seconding Madison. It's a cute little town. Did it as a weekend trip when I lived in Chicago. Beware it is very collegey (obviously) and this weekend could be overrun with excitable, just returned, inebriated undergrads.
posted by sneakin at 3:13 PM on August 28, 2007

I would suggest a trip west to the Mississippi and then north along either the west or east side as far as you're willing to go. That part of the country is incredibly beautiful, and it would be pretty interesting to see the way that the land has changed after the torrential rains that went through there this past week and caused horrible flooding.
posted by yellowbkpk at 3:18 PM on August 28, 2007

Come see us in Madison! It's Taste of Madison this weekend, and the Saturday morning farmer's market is at the height of summer richness, even after the flood damage. I hear it's easy to Priceline nice hotels cheap here, though since I live here I've never done it.

If you do press on farther into Wisconsin, I second the Hotel Trempeleau -- even if you don't stay, it's a great place to eat dinner and watch the river laze by. And see the bluffs at La Crosse.
posted by escabeche at 3:46 PM on August 28, 2007

Maybe visit Door County? It's a little far, but this bed and breakfast is really cozy and romantic....I highly recommend it.
posted by quentiniii at 3:48 PM on August 28, 2007 [1 favorite]

Thirding Trempealeau Hotel, or stay in Winona, it's a beautiful town not too far from the T.H. (North, 20 mi.)
posted by wafaa at 4:11 PM on August 28, 2007

Mineral Point, Wisconsin. Cute, small, walk-able, and quiet. Lots of little artsy bits. Beautiful B&Bs like this one where we stayed (very nice). Not very expensive either.
posted by answergrape at 4:20 PM on August 28, 2007

Response by poster: thank you for the great suggestions everyone and keep them coming! Unfortunately, Madison is out as Sneakin may be right: my girlfriend's brother is a student at Madison and moves in this weekend and starts classes on Monday.

For those following this thread for themselves, some suggestions we've gotten from friends are: Leland, MI and New Glarus, WI. Can anyone comment on these places?
posted by AceRock at 4:20 PM on August 28, 2007

Seconding Door County - it's really beautiful this time of year especially. Try to hit a "fish boil" for some local color.
posted by MiffyCLB at 4:32 PM on August 28, 2007

The best beer in the midwest, New Glarus, can't be had in Chicago anymore. Something about extortionary beer distributors and the company swearing off their thirsty brethren to the south. So go there. Try the Spotted Cow.
posted by felix betachat at 4:33 PM on August 28, 2007

Leelanau County, Michigan, of which Leland is the county seat, is one of my favorite places in the world, FWIW.

Absolutely beautiful. Especially this time of year. Lots of wineries, beaches, orchards, and general good feelings.

Black Star Farms is an area winery which is quite nice. But there are quite a few actually. Madonna's father has a winery in Leelanau County, as well. Madonna the pop star, not the blessed virgin...

I'm from the area, and I'm going back this weekend. I'm quite excited.

Sleeping Bear Dunes National Seashore is close, too. Nice beaches, big dunes, scenery up the wazzoo.

About 5 1/2 hours north of Chicago. Enjoy your weekend...
posted by katocolon at 4:39 PM on August 28, 2007

Indiana is not an option? Not even some of the lakes in the northern part of the state like Winona Lake?

How about Yellow Springs, Ohio, then? It's an artisan / hippie town with a nice shady river gorge for day hikes, a great sandwich shop that bakes its own bread, and the nearby Youngs Dairy for ice cream.
posted by salvia at 4:58 PM on August 28, 2007

I am partial to New buffalo Michigan, but I went 10 years ago so not up on the latest.
posted by JohnnyGunn at 5:22 PM on August 28, 2007

Spent a drunken evening at a brewery/pub in New Glarus, which is home to the midwest's largest urinal. It's true! Stayed at a David Lynchian motel and had dinner at the nearby Culver's. Great trip! Though I don't remember much else. I hear there's more to do, but can only point you in this direction.
posted by Work to Live at 6:34 PM on August 28, 2007 [1 favorite]

P.S. We are driving to the Twin Cities this weekend, to partake of the Minnesota State Fair.
posted by Work to Live at 7:19 PM on August 28, 2007 [1 favorite]

Port Clinton, Ohio and the Lake Erie Islands. You'll think you're on Cape Cod, except with nice flat midwestern accents.
posted by nax at 7:50 PM on August 28, 2007

I had a great time driving along the Great River Road. You could do this and go to Minneapolis at the same time.

There are other road trips on this site you can get inspired by as well.
posted by rsol44 at 4:25 AM on August 29, 2007

How about Saugatuck or Grand Haven. Both are relatively close to Chicago. Nice way to spend a day or two.
posted by jasondigitized at 4:39 AM on August 29, 2007

It's about 10 hours , which may be too far for a weekend but the drive to Ithaca NY would be nice. You go right along Lake Erie for a while...
posted by doppleradar at 6:06 AM on August 29, 2007

If Door County looks interesting but too built-up, how about Bayfield and the Apostle Islands? That part of Wisconsin is gorgeous, and you can ferry out to Madeline Island for the full-on nautical-stay experience. About 45 minutes from Bayfield, there's some really cool hiking above and around the sea caves in the sandstone cliffs on Superior.

Of course, for the absolute accept-no-substitutes flat out most naturally beautiful area in the upper midwest, your best bet is the north shore of Superior, the stretch of Minnesota north of Duluth (and Duluth itself is a pretty cool place to stay). Drive to Duluth, spend a day there, then head up 61 and hike at some of the state parks (there are 5 or 6, and they're all great-- Temperence River and tettegouche are probably my favorites, but you really can't go wrong with any of them), check out some of the Superior Hiking Trail, hang out in Grand Marais, grab a hotel somewhere; if you like the outdoors at all, you'll love it up there.
posted by COBRA! at 7:33 AM on August 29, 2007

Oh hey, if you're architecture fans you could go to Frank Lloyd Wright's workshop at Taliesin, just outside Spring Green, WI. New Glarus isn't far from there, and you could also hit the Mustard Museum in Mt. Horeb.
posted by escabeche at 7:49 AM on August 29, 2007

If you're going to Door County, make sure you make it to Adult night at the Art Barn.
posted by achmorrison at 7:54 AM on August 29, 2007

In an identical position, Ms Meat and I have recently gone to:
Oregon, IL home of some state park with cabins and trees and quaint small town goodness.

Cassopolis, MI very similar with small pretty lakes.

Woodstock, IL filming location of Groundhog Day! It's reachable by train if you want, and has several nice B&Bs along with a cool farmer's market / town fun in the square on saturday morning. There's berry picking nearby.
posted by a robot made out of meat at 8:06 AM on August 29, 2007

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