We are definitely road trippers - both enjoy driving - especially through beautiful countryside. But when we get to a city we actually want to see it and spend 3 or 4 nights there - depending on the size.

You are doing all of the driving - lots and lots of driving - but really laving no time to see the sights at any of the places you're staying.

You can certainly cover that much ground - but if you will enjoy it is something else again. Not sure how much of Niagara you will see in a few hours - or Ottawa. And IMHO you are really racing through Maine - not sure you will have time to enjoy exploring any of the small towns or walk along the shoreline or even just stop to have a relaxed lobster roll.

Note that Montreal and Quebec are still in Quebec (QC) not ON, last I heard, You may have some Canadians riot here!

This isn't the way I travel, but I get that long drives are fine for you, What I don't quite understand is what you plan to see along the way.

For example, there's a huge number of sites between Boston and Cape Elizabeth!
Portsmouth NH, York ME with it's iconic lighthouse, Ogunquit

This itinerary looks like you only really want to see a few places--Bar Harbor, Quebec, Montreal, Ontario and the rest is filler.
"We like to see as much as possible and we are not beach vacationers" With this schedule, you're seeing a few big cities and some roads. As long as you're driving, why not see some of the smaller places the area is known for instead of zipping past them?

You've said what you don't like--beaches--but what do you like to do or see?

Also,make sure to add in enough time in your schedule to cross US/Canadian borders, You never know how long it might take. You'll be traveling over Labor Day weekend when traffic can be bad in some areas

It's do-able but I think you would miss a lot of Maine. I would visit Maine Coastal Gardens near Boothbay and time my visit to the Owls Head area to have lobster lunch at Waterman's Beach. Owls Head Transportation Museum usually does extra things on weekends. One year we saw a restored Lombard Log Hauler and it's very interesting when the antique airplane owners fly their planes.

We usually spend a week exploring back roads in Maine. You can still do a lot of driving but I think you would see more scenery. And do NOT miss Camden ME.

It seems indeed like we might have been somewhat overambitious in our planning . Think we will skip the Canadian part of this planning and focus on the Maine part of the trip here.
Since we are coming from Chicago, do you think the best way to do this trip is a round-trip starting and ending in Boston (do not really need to visit Boston, been there 2 times before - so we can focus on Maine).
And can you recommend the main focus points for this Maine roundtrip, taking into account our total time there (Sat 8/24 - Wed 09/04)? We could potentially also switch the period from Sat 08/31 until Wed 09/11. What would be the better period?

Any other tips or suggestions are also welcome.

You only have a day in Quebec City, and you need two at least.

I agree with all the suggestions above except to confirm what dfrostnh says, most of the scenery in Maine is not on the big highways but down the side roads.

If you want to see what people mean when they say "the scenic coast of Maine" you will have to go to places on the back roads: Bailey's Island, Popham Beach, Friendship, Port Clyde, Tennants Harbor, etc.

I will cause a storm but much of what you see in rural Maine on the main highways is not hugely different from what you would see in northern Alabama, including the old cars up on concrete blocks.

Two notes regarding the car: you will certainly need special paperwork and you may need special insurance riders to take the car into Canada and back to the US. I suppose you know what the dropoff fee will be for leaving a Boston car in Chicago (or Buffalo, since it isn't clear what you are doing at that point).

You may find it 10% cheaper to pick up your rental car outside the city of Boston. They add a large tax to the price to pay for their convention center. Cambridge is a separate city, and there are rentals in Kendall Square.

Finally, I would stay on the Canadian side of Niagara Falls rather than on the US side. It is nicer.

Go for the cheapest airfare - maybe southwest to Manchester NH if SW is still doing free checked baggage. You might also find cars are cheaper to rent in Manchester (MHT). You will be less than an hour from Portsmouth NH on the coast (a great stopping place) and easy connect to I95 if you want to zoom right to Maine (which is actually right over the river.

Keep in mind the dates for Labor Day weekend and expect it might be hard to find accommodations in southern ME that weekend but rates might drop after Labor Day weekend depending on where you stay.

I would also check to see if the great lobster shacks are going to be closed weekdays after labor day. These are the places on docks, no heat, and dependent on summer help that might be open weekends only after labor day. You can google best lobster for a list. Here's the hours at Five Islands to give you and idea
http://fiveislandslobster.com/

so if you want lobster at a sunny picnic table, I would choose your earlier dates. There are some places like Camden that will be very busy on Labor Day weekend even that far north but I think there will be plenty of accommodations available.

We haven't been north of Ellsworth in a number of years so I'm not sure how busy Bar Harbor will be Labor Day w/e. What we like to do is top someplace scenic for a break. We carry bag chairs in the car and picnic supplies. It might be sitting in the little pine grove next to Pemaquid Point lighthouse or someplace in the Harpswell area. Drive backroads aiming for a good lobster lunch someplace. More driving. Stop for scenery break, iced tea and snack, maybe a little reading or staring at the ocean (don't forget binnoculars), then back to lodging place.

I would also take a boat ride whether it be out of Portsmouth NH, the mailboat that goes around Casco Bay/Portland ME or a lighthouse cruise. You can also get a map from the state dept of Agriculture to find wineries or other food places.

The mailboat in Portland is one of the last great bargains in America. You get a tour -- somewhat narrated -- of the islands of Casco Bay at a very cheap rate because the boat is subsidized to carry mail and freight to residents.

Thank you all for your feedback. This made us rethink our itinerary and we decided to leave Canada for a next trip. Instead, we are going to combine Maine, Vermont and New Hampshire for this trip. The reason why we decided to fly into Boston is the price of the flights (we are flying in from Peoria to Chicago to Boston). Flying from Peoria to Portland would be double the price.

This is the itinerary we came up with. We would appreciate your feedback on this, either the itinerary itself, or the places to stay overnight.

08/24/13: Peoria, IL - Boston, MA

Boston, MA - Portland, ME (or Cape Elizabeth, ME) (110 mi/1:58) (Via Portsmouth, NH)

08/25/13: Portland, ME - Bar Harbor, ME (192 mi/4:31) (Shopping in Freeport, via US 1 through Bath. Spend part of day around Boothbay Harbor, Camdon or Blue Hill)

08/26/13: Bar Harbor, ME (Acadia National Park)

08/27/13: Bar Harbor, ME

08/28/13: Bar Harbor, ME - Bethel, ME (85,1 mi/2:05) (Via Portland, ME (Casco Bay Lines Cruise - Mailboat) to Bethel (via Sabbathday Lake & Poland Spring))

08/29/13: Bethel, ME - Lincoln, NH (88,5 mi/2:09) (Via Gorham NH, Pinkham Notch, Glen, Conway, Kancamagus Highway (White Mountains))

08/30/13: Lincoln, NH - Burlington, VT (123 mi/2:18) (Via Franconia Notch (Flume Gorge), Littleton, Rock of Ages granite quarry, Hope Cemetary, Barre, Montpelier)

08/31/13: Burlington, VT - Woodstock, VT (105 mi/2:41) (Via Middlebury (Gap), Hancock, Plymouth)

09/01/13: Woodstock, VT - Manchester, VT (57,7 mi/1:28) (Explore villages southern Vermont: Manchester, Dorset, Grafton, Newfane, Weston)

09/02/13: Manchester, VT - Bennington, VT (50,7 mi/1:18) (Via Arlington to Bennington. Go across MA state line and visit Williamstown. Back to Bennington (VT))

09/03/13: Bennington, VT - Boston, MA (154 mi/3:44) (Via Route 9 (Molly Stark Trail), Marlboro, Brattleboro, Keene (NH), Mount Monadnock to Boston (spend afternoon/night in Boston))

09/04/13: Boston, MA - Peoria, IL

Thank you guys for your patience and all input!

Did you check airfare to MHT? I flew to Peoria a few years ago and THINK I went out of MHT. I don't go to Boston unless the fare is a lot cheaper.

If you stop at the Vermont Country Store, you better figure on at least an hour.

If you are driving Rt 101 from Keene past Mt Monadnock, you're going to drive right by Yankee Magazine's headquarters in Dublin NH. Hope you check their website for photos and suggested scenic routes thru New England. I would have lunch in Peterborough NH, a sweet little town, before heading to Boston.

I would love to go on this trip!

With a couple of exceptions.

Coming back to Portland on the way to Bethel doesn't make any sense. Take US 2.

When you stop in Portland on the way up, then take the mailboat cruise, weather permitting. What else to do in Portland? walk around, eat, small but excellent art museum, go to a Sea Dogs game: these people love minor league baseball and it is cheap and fun. Drive out to Portland Head light on Cape Elizabeth. It is the lighthouse of your dreams.

I think Ackislander and I should plan out the perfect trip to Maine and then test it out. I haven't been to Portland Head light!

Hmmm, dfrost! That could be arranged, as long as my wife and I don't have to camp!

In addition to everything else, I also want to go to the newly opened Winslow Homer studio in Prouts Neck, but it is a tough ticket! Too much stuff too little time.