Driving New York to Chicago
November 29, 2008 2:20 PM   Subscribe

This coming week, I'll be driving from New York to Chicago. I'm not in a major rush to get there and would like to make the trip fun (I'll be traveling with my girlfriend). What are some points of interest along the way? Scenic routes that don't take me way, way off course? Good food? Interesting towns? I'm thinking three days and two nights will give me some time to enjoy the trip, yes?
posted by SampleSize to Travel & Transportation (11 answers total) 3 users marked this as a favorite
Here are some answers to the same question for a Minneapolis to New York road trip.
posted by fundip at 2:36 PM on November 29, 2008

Well, if you're taking I-90, you're going right past the Rock and Roll Hall of Fame and Museum. I mean, you can see it from the Freeway. So just get off at the East 9th Street Exit in Cleveland, and take a right (don't drive off the end of the pier). See the very piano Jerry Lee Lewis played in his earliest Sun Records recordings. See the Sun Recordings tape machine and control room that recorded "That's All Right Mama." Gaze in wonder.
posted by Faze at 3:27 PM on November 29, 2008

Unfortunately[?], the most direct route from NYC to Chicago is I-80, which is primarily rural/small town America in a fairly bland way. The Delaware Water Gap might be a good place to stretch your legs if the weather is cooperating. Oh, there's also a fair amount of outlet shopping, if that's your thing.
posted by anarchivist at 3:40 PM on November 29, 2008

The University of Notre Dame is in South Bend, IN.

The towns along the southeastern shore of Lake Michigan (New Buffalo and Union Pier, both in MI) are where some Chicagoans have weekend or summer places. There are some nice restaurants and views of the sunset over the lake. If you want to go further north out of your way, South Haven and then the Saugatuck/Douglas area are neat little towns with artsy areas and again, nice views of the sunset. Not a whole lot will be happening in these places in the off-season, but they are nice to drive through if you have the time.

There are casinos in Gary, Hammond and Michigan City (IN) if that's your thing.
posted by SuperSquirrel at 4:04 PM on November 29, 2008

Swing north through Ann Arbor. Stop at the Borders store #1 in downtown. There are a bunch of new casinos in Detroit as well as some across the river in Canada.

It's the wrong time of year but if you drive this route in the summer, consider spending a day at Cedar Point in Sandusky, OH -- home of some of the biggest, baddest, tallest, fastest roller coasters in the world.

If you don't mind chain hotels, the best one I've ever stayed at is the Holiday Inn Express in Clearfield, PA. It's new, clean and the staff is great.

For a more scenic route, drive through New York instead of Pennsylvania. Take 17 to I-86 west to I-90 back down to Cleveland. It has a whole lot less traffic than I-80 and many stretches of practically nothing, but lots of small towns with character. I only advise taking this route if the weather is good. I once drove it going east and spent way too many hours driving through white-out conditions where I was literally the only car on the road for a hundred miles.
posted by camworld at 4:40 PM on November 29, 2008 [1 favorite]

If you plan on going route 80, Hershey, PA is a chocolate lovers dream. It's also in the heart of Amish country, the only place to get shoo-fly pie. Also on the route is Steamtown in Scranton, a steam train museum if you love the big iron.

It's a little out of the way, but the Corning Museum of Glass is really amazing.
posted by Marky at 4:43 PM on November 29, 2008

I'll second Cleveland area. Tons of interesting food options, including Iron Chef Micheal Symon's two restaurants. Check out old-school Polish cafeteria Sokolowski's University Inn. Lots of good food recommendations here.

Cuyahoga Valley National Park is a quick zip from the Interstate. Beautiful falls and trails.
posted by smelvis at 6:05 PM on November 29, 2008

The Cleveland and Toledo Museums of Art are both first rate. The Toledo museum has a great collection of glass from antiquity to the present.

Youngstown has two museums that I really enjoyed when I passed through last year: The Youngstown Historical Center of Industry and Labor and the Butler Institute of American Art.

For a slightly less touristy Amish experience, try Shipshewana in northeastern Indiana. If you are passing through on Wednesday don't miss the antique and livestock auctions. A short side trip down I-89 in Indiana will get you to Auburn, home of the wonderful Auburn-Cord-Duesenberg Museum. You don't have to be a car buff to enjoy it.

Also, seconding what camworld says about I-90 across NY being the more scenic and enjoyable route. Also, as a native upstate NYer, seconding camworld's advice about the weather. If you see a forecast for lake effect snow in Syracuse, Rochester or Buffalo head for I-80.
posted by plastic_animals at 8:06 PM on November 29, 2008 [1 favorite]

If you go through Binghamton NY, stop in Endwell at the Spiedie 'n' Rib Pit (unless you're a vegetarian.) Their pork and chicken spiedies are great!

Depending on the weather, you can take a waterfall drive of New York State--Chittenango Falls, one near Ithaca whose name I can't remember, the fabulous Watkins Glen and two smaller ones nearby (Havana Glen is the one I can remember), and many falls at Lechmere state park.

On the other hand, if you go along Route 80, there is a series of amazing falls at Ricketts Glen State Park. This is a steep, sometimes slippery climb with no handrails. Best not done during/after rain or snow.

If you go near State College PA, try Irving's bagels--the best. The Creamery on the Penn State campus makes really rich ice cream.
posted by sevenstars at 6:00 AM on November 30, 2008

If you see a forecast for lake effect snow in Syracuse, Rochester or Buffalo head for I-80.

And the same warning goes for northwest Indiana or southwest Michigan. But get off I-80 instead! Lake effect snow is a real mess to drive through, and can come up with little warning, so pay attention to the weather reports.
posted by SuperSquirrel at 7:15 AM on November 30, 2008 [1 favorite]

Stop in on Pymatuning reservoir at Linesville, PA, where the ducks walk on the fish. Not far from I-90 or I-80.
posted by sagwalla at 2:31 PM on December 1, 2008

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