Hey guys, I'm trying to put together the five best weekend getaways from Chicago. Ideally, I'd like to find a fun, out of the way destination, a good "backroads" drive to get there and a different route back. Any scenic stops along the way would also be really helpful (historical sites, fruit picking orchards, whatever). The more specific you can be, the better.

Thanks!

 

lake shore drive at 3am

 

Drive south into Indiana.... (I know that parts is hell) Once in the state take 94 to IN 249 Portage exit.... Go north on 249 to the RT 12 exit.. Take 12 all the way into New Buffalo MI. Stop at Redamacs, grab a burger..(you will be glad you stopped)... The Lake is but a block before and 3 blks north of Redamacs....
Get back on 12 this will take you back to 94... Take 94 to St Joseph... Get off NB on Buisness 94... Check out Benton Harbors Lake shore.... B94 will dump you onto M63... Which turns into A2... This will wind you up the lake shore to Holland MI. Merges with 196 there... which will turn into M31... Which will take you thru Grand Haven and Ferriesburg.... You will come to Buisness Rt 31 west... This will take you into the downtown Muskegon area.... Head torwards the Lake and you will find the Bay.... This is the MIchigan port for the SS Badger... This is a large cruise ship like car ferry... for around 100 bucks you can sail across the lake in 4 hrs. Cruiseship style.. IE they have a bar on board.... This will take you to Manatowac WI... where you can take 43 to 94 to get back to Area....

Not for everyone... But a thought just the same... I have taken this trip a few times.... Enjoyed it every time....

There are plenty of restaurants and winerys around lower MI... (Skips in Benton Harbor.. good choise) Not to mention the sportfishing and roads to no where in between....

Patrick

P.S. If you hit Muskegon before 9 there time you can take the Badger across overnight... Ship leaves port at 10:30pm gets you to WI by morning.... May have to check their schedule though been a few years since the last time I sailed....


Man didnt see you were from NY... welll a trip for another time I guess

 

I really miss the East Coast sometimes.... like when I'm looking for a hill or something. Damn flat, straight roads.

There are a lot of vineyards in Southwest Michigan. They all connect through a bunch of twisty two-laners, but there are a lot of drunk wine tasters around. Great area to get some great inexpensive wine from the wineries, there are a lot of bed/breakfasts, and there's the beach right there.

Going North on Sheridan Road (once you get out of the city)... it starts twisting back and forth, and up and down... until you hit Lake Cook Rd. It's a lot of fun, unless you have someone really slow in front of you. Not exactly a weekend get-away, but a nice local drive.

 

Up along the Mississippi River towards Twin Cities. You get in the bluffs and the roads just turn & turn. Many little towns with interesting shops.

 

absolutely depends if you have a chic w/ you.

easily the most 'scenic' (and touristy) weekend getaway ex-Chicago would be to Galena: http://www.galena.org/

plenty of golfing, lots and lots of B&Bs, cute restaurants (tho NOT fine dining by any means), much antiquing and only 1 county route to get there. you also have U.S. grant's house, much hiking by the miss. river.

i haven't explored the 'driving' nearby, but... it's IL, don't expect much.

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also highly rec Minneapolis (as per the poster above). it's the next Seattle. lovely vibe, tremendous dining... i mean, we're talking about possibly THEE best true-to-form french baguette West of NYC. I flew 3 loaves in, froze it in the freezer and retoasted them for the next week. in this relatively small town, there are 3 "authentic" french bakeries. unheard of in the midwest. i'd do nothing but eat and drink in this town. lovely coffee shops, clean hipster downtown.

what i wouldn't rec is cleveland, oh... just cuz i got molested by a BBW at the local happy hour last nite...

 

Wow, I'm going to try this in August

Sounds great except I think I'll continue north on 94 up to Door County and spend a weekend up there at the summer house

 

The boat ride is worth the money....

I love Door county...... Fish boils rule..... Not to mention the great scenery...

Patrick