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  1. Default Washington DC-Chicago-20 Day RoadTrip

    Last year I found it easy to organise a West Coast roadtrip because there was so much information.

    This year we leave at the beginning of July and fly into Washington DC. We then depart 20 days later from Chicago.

    We plan on spending some time in Washington and in Chicago but don't know what else to do. Kids want to see New York, I would like to see Boston and my hubby would like to venture over to Canada. We also love visiting small places as well as the big cities. It's difficult to please everyone as some like sightseeing others shopping so a mixture of both would be ideal.

    Any advice on a route? Don't know where to start!

  2. #2
    Join Date
    Mar 2005
    Washington state coast/Olympic Peninsula

    Default There's lots of good info here on the East Coast

    It think it just might take a bit more poking around to find it.

    A drive like this might fit your needs. A few days in each city, with a few days taken to explore the points in-between, might make a nice mix.

    And this post has several links to posts about the Northeast. Why don't you poke around them and get some ideas. We'll be glad to help you tweak as needed, and offer recommendations when we can.

  3. #3
    Join Date
    Mar 2005
    Tucson, AZ

    Default All Kinds of Information Everywhere

    A route from Washington to New York and then Boston, up through New England to Montréal, up the St. Lawrence to the Thousand Lakes Region, one way or the other around Lake Ontario to Niagara Falls before making the final run to Chicago, all within your 20 day schedule. There are plenty of discussions of each part of such a trip on these forums but to get the full benefit of them you'll have to familiarize yourself with the Search tool at the left edge of the second green toolbar at the top of this page and the Similar Threads listed at the bottom of each page. Then spend some time wandering the many nooks and crannies of this site and daydream about what might appeal to you. Oh, and get your husband and kids a bit more involved - What exactly would they like to see and do in New York, Boston, Canada, wherever.


  4. Default

    Thanks PNW Judy and AZ Buck for your replies and advice. I'll have at the links and a hunt around the site. Much appreciated help, thanks.

  5. Default

    Me again! Slight change of plan. Now flying into Chicago and leaving from Washington. Still have 20 nights.

    Trying to do an itinerary, can you give me any advice on anything I'm missing out on -

    Chicago (3 nights)

    Detroit (only chose this as a halfway stop but would you suggest somewhere else i.e. Ann Arbor, Windsor? (1 night)

    Toronto (2 nights)

    Niagra Falls (then 1 night somewhere - Syracuse?)

    Boston (3 nights)

    Providence (1 night - or somewhere else?)

    New York City (5 nights)

    Philadelphia (1 night)

    Baltimore (1 night)

    Washington DC (2 nights)

    Your advice and knowledge as always would be much appreciated.

  6. #6
    Join Date
    Oct 2008
    Joplin MO


    Chicago to Toronto is 520 miles via fastest route and can be done in 1 long day, use I-69 to cross the border at Port Huron/Sarnia. I hate to say anything bad about any of our cities, but Detroit is probably one of the last places I'd want to explore and stay in these days.

    Another option would be to go north from Chicago through Wisconsin and the Michigan upper peninsula and cross the border at Sault St. Marie, and go to Toronto through Sudbury. I'd allow 3 days if you choose that.

    I'd spend the night near Niagara Falls - from there to Boston is also doable in one day.

    I'd go from Boston to NYC in one day - there really isn't much to be said about Providence - but you may want to detour out to Cape Cod and/or down through Newport and stay somewhere whenever the time requires. Same with Philly to DC - no need to stay in Baltimore.

    In general, it's more costly to stay *IN* a large city than it is along the highway in less populated areas, keep that in mind.

    If you plan on going through Canada, make sure you have everything set for border crossings - proper visas if required, permission from the car rental company, etc.

  7. Default

    Thanks glc, I'll look into your suggestions, much appreciated.

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