Cool Stops/Scenic Routing between Chicago and NYC?

May 22, 2021 9:12 PM

I am going to take a leisurely roadtrip from through the central midwest to New York Traveling solo by car from the first time in a long time, looking for scenic stops along the way and pretty roads between.

Thinking about a 3 day trip affair, but happy to extend a day or two as well.

Day 1
from Chicago to Cleveland
Day 2
Cleveland to Falling Water+Pittsburgh
Day 3
Pittsburgh to NYC

interested in pretty roads, neat <2 hour stops in nature, cool shopping/downtown plazas

Quirky places

Yay!
Thank you Metafilter!

posted by wowenthusiast to Travel & Transportation around Midwest, WY (10 answers total)

New Hope, PA / Lambertville, NJ. They're across the river from each other and you can walk across. Cute downtowns, art, food.

Jim Thorpe, PA similar feel, though a little larger.

Bushkill Falls, PA might be a bit out of the way.

Easton, PA has some stuff you can check out.

Spruce Run Recreation Area, Clinton, NJ

Watchung Reservation, mountainside, NJ
posted by pyro979 at 4:33 AM on May 23, 2021 [1 favorite]

As a longtime Columbus resident, I would suggest Chicago-to-Columbus instead of Cleveland. That would allow you to stop in Yellow Springs, Ohio (nature, cool shopping, and quirky all in one), off I-70, without adding all that much time. Troy, Ohio is nice, as well, but they’re too close together to do both. In Columbus, the interesting neighborhoods are Grandview, the Short North, and Clintonville.

Whichever you choose, your second day will be much shorter than your first or third. Columbus to Pittsburgh is only like three hours. Cleveland to Pittsburgh is even less. If you do Columbus, probably the most interesting thing between there and Pittsburgh is The Wilds, which is an exotic animal preserve in Zanesville. Zanesville itself is pretty boring, but there’s a wonderful old school ice cream place called Tom’s Ice Cream Bowl, although you might pass through too early.

Also, Fallingwater is a good hour southeast of Pittsburgh. If you’re planning on going to Fallingwater on day two, then returning to Pittsburgh, you’re wasting a couple of hours. There’s a few things to do in and around Somerset, PA, and that might be a better second stop. Pittsburgh sucks anyway. ;)
posted by kevinbelt at 5:21 AM on May 23, 2021 [1 favorite]

White Turkey in Conneaut, Ohio is a good place to stop for lunch off of 90 after Cleveland. There's good rootbeer and hummingbirds to watch. It may be quite busy depending on when you stop.
posted by graxe at 6:51 AM on May 23, 2021 [1 favorite]

Not sure how well this would fit into your plan since it is only a couple of hours from Chicago. On our last trip back to Chicago from visiting family in Ohio, we discovered Das Dutchman Essenhaus, an Amish restaurant and shopping village, and it was a very enjoyable break in our drive. The route off of the tollway to get there was very scenic and pretty, and the area surrounding the restaurant is charming. Food was excellent, we ate off of the buffet and everything was great. Highly recommend the beef and noodles spooned over mashed potatoes! (Not sure if they are doing buffet during Covid but they have a menu as well.)

The gift shop was really nice. The website says they have five shops including a bakery. I'm not sure we saw everything, we just wandered around in whatever was connected to the restaurant. I don't know when my next trip back to Ohio will be since my dad is dragging his feet about getting vaccinated, so since we're not likely to be in a position to just "stop in" while passing by anytime soon, I'm thinking of making a day trip to this place just to eat and shop. The beef and noodles is calling me... lol.
posted by Serene Empress Dork at 7:07 AM on May 23, 2021 [1 favorite]

Whenever I am anywhere near Cleveland, my must-visit place is the West Side Market! So many awesome vendors and delicious food, and really fun to just walk around and take it all in.

In my experience, taking highway 80 through PA is one of the longest and most boring parts of a road trip I've ever done, so maybe avoid that in favor of smaller, more scenic byways, a different route entirely, or plan lots of fun detours off of that section specifically.
posted by carlypennylane at 7:47 AM on May 23, 2021 [1 favorite]

I did a version of this recently, and can heartily recommend a day that starts with breakfast in Yellow Springs, Ohio (like Kevinbelt mentioned above), proceeds to the Great Serpent Mound, stops for a late lunch and downtown wander in Athens, Ohio, then finishes up at an inn south of Pittsburgh about 20 minutes from Fallingwater. Stick to scenic byways and two-lane roads, of course.
posted by minervous at 9:52 AM on May 23, 2021

I recently drove from Chicago to NYC and back. My route was slightly different (I-80 all the way), but a few recommendations for the Chicago-Cleveland part of the trip:

Pokagon State Park is a really nice state park near Fort Wayne, IN with a great old school hotel, a lake, and lots of hking.

Toledo's a quick drive from the Ohio Turnpike and lots of options for restaurants and a great art museum. The city itself is pretty sprawl-y, but the suburb of Perrysburg has a nice, walkable downtown.

Cuyahoga Valley National Park.

For quirky places, Dave Grohl Alley (home to the world's largest drumsticks!) in Warren, OH should fit the bill.

Have a great trip!
posted by huskerdont at 11:48 AM on May 23, 2021 [1 favorite]

I’ve been driving between Cleveland and Detroit over the last year to visit family and have taken 2 instead of 80/90 for a stretch somewhere between Cleveland and Toledo. It’s more scenic and for I prefer the less busy roads for the five to ten minutes it adds to my drive.

The route winds closer to Lake Erie and there are a few beach towns. I stopped on Tuesday’s drive to visit the Marblehead Lighthouse. There’s another lighthouse 14 miles from it in Port Clinton.
posted by icaicaer at 4:32 PM on May 23, 2021 [1 favorite]

Yes, Fallingwater is a decent trip outside of Pittsburgh. However, if you're into FLW, you should also see if you can schedule time into seeing Kentuck Knob (my favorite over Fallingwater, also has a large outdoor art collection) and if you're overnighting, seeing if you can stay at Polymath Park. In that general area also is Ohiopyle State Park if you want nice hiking and waterfalls.

There's a little town called Ligonier down that way that has some cute shopping, think cute like Gilmore Girls adorable (there is a gazebo). There's also a historical fort that's actually pretty interesting. You won't be that far off of Fort Necessity national battlefield too, if you like history.

All that said, I'm a Pittsburgher, so if you do want to come visit our amazing city, I'd highly recommend it. :)
posted by librarianamy at 6:57 AM on May 24, 2021

There are several very cool mound sites not far from that route. Grave Creek has a museum.
posted by eotvos at 6:57 AM on May 24, 2021