Welcome to Fodors Jen_. You will get LOTS of help here -- but not exactly here

You have posted on the Travel Tips forum which is more for general travel talk. Destination-specific questions/threads get much more activity on the geographical boards (USA, Europe, Asia, etc).

See the 'Change Forum' pull down menu? Click that, go over to the United States board and re-post your questions there.

Thank you

You're welcome. Response might be a little slower than normal due to the holiday weekend but you should get lots of help over there.

Are you planning to drive straight through to Bangor or are you taking it slowly?
There’s the obvious fast route, taking the Interstates from Cleveland to Bangor, then there’s the scenic route. The scenic route will add some time to the drive but you’ll see some nice sites along the way.
Have you ever been to New England before? The drive through VT and NH to ME is nice with nice mountain views. Fishing is easy to access and there is plenty of hiking along the way. If you look at the maps and drive through Rutland, VT you will drive by Killington, VT on Route 4 into Woodstock, VT. Woodstock, VT is a nice, although expensive, town. Be sure to abide the speed limit in town. Continue on Route 4 to Route 89 south, take Route 91 north to Woodsville, NH. Take Route 302/ 10 to NH Route 112 east. This is the west end of the Kangamagus Highway. Take this into North Woodstock, NH. This is a small NH village with a few restaurants, Truants Tavern, and The Woodstock Station and Brewery, and shops. Continue to Lincoln and onto Conway, NH. You will be driving through the heart of the White Mountain National Forest. There are so many hiking trails here you need a guide book. First, stop into the Mountain Wanderer book store in Lincoln and ask the store owner, Steve, for some hiking advice for a trip to suite your time constraints. If you don’t have time to hike try to arrange the drive time during daylight to see the views, they are amazing. Conway is not too much but does have a great Mexican restaurant, Café Noche, right on Route 16. Aa little north on Route 16 is North Conway. This is another touristy New England village. There are also tons of restaurants and shopping outlets. I ignore the outlets and go the center of town. There are good restaurants here too, Rafferty’s and Horsefeathers. It’s about 3 hours from North Conway to Bangor. You’ll be seeing the back woods of Maine and opportunity to see moose.
In Maine you have to visit Belfast, Camden and Rockland. These are all on the coast on Route 1. Route 1 goes from Key West, FL to Madawaska, ME on the Canadian border.
On the way back you could stop into Cooperstown, NY and visit the Baseball Hall of Fame. This takes a whole day to appreciate.