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  1. #1

    Default Summer east coast road trip Philly to Williamsburg VA

    We are a family of four starting & finishing in Philadelphia PA, the 1st leg of our trip is pretty much planned out, Philly -Baltimore-DC, due to the 1st three stops being cities we are avoiding parking charges & taking the train as not much need to pay 8 days car hire to have it sat in expensive city hotel car parks while we do the city tourist thing, the 2nd leg of our trip is where any input would really help, we are picking up a rental car from Union station DC on day 9, we are heading to Winchester VA for a one night stay we plan to go to the Family drive in movie theatre there to take in a couple of movies in the 50`s drive in, the next day we head to Front Royal & drive along Skyline drive as far as Swift run gap & head for Stanardsville where we have rented a log cabin for 3 nights before heading to Williamsburg VA via Richmond, we have 4 nights in Williamsburg followed by a drive back to DC for a 1 night stopover before driving back to Philly for our return flight.
    Any help with good old diners either between DC & Winchester or around Winchester also any must see sights , also any tips for our stay in Stanardsville for the surrounding area as far as wineries/historic sites things for family days out etc in the Shenandoah Valley, also in & around Richmond any tips on real BBQ joints & the must see in Richmond, in Willamsburg we plan to visit Colonial Williamsburg & Busch Gardens these will eat some serious hours so any other must do`s ? eg Yorktown & recommended restaurants/diners in the area, also any tips on visiting Philadelphia/Baltimore & DC would be great, our Children are aged 11 & 17 & we are travelling in early August

  2. #2
    Join Date
    Mar 2005
    Tucson, AZ

    Default Williamsburg and Back to Washington

    Welcome aboard the RoadTrip America Forums!

    I have a few suggestions for you that relate to the last part of your trip. In addition to Williamsburg and Yorktown, there is a third 'leg' to the Historic Triangle and that is Jamestown. I also think your children would thoroughly enjoy a ride to the south bank of the James River on the Jamestown-Scotland Ferry. If you do these two on the last day of your time in Williamsburg, then you can continue around Norfolk to Virginia Beach and then take the Chesapeake Bay Bridge-Tunnel over to the Delmarva Peninsula and take that up through towns like Crisfield and St. Michaels before using the Chesapeake By Bridge to cross the bay beak to Annapolis and Washington.


  3. #3


    Thanks, we had looked at going back towards DC via an alternative route & had looked at more or less the same route as you suggest with the exception of the 1st part going via Jamestown to Virginia beach, as far as I got was crossing by way of the Chesapeake tunnel/bridge & crossing over to Annapolis to DC, I dont know much about the Delmarva Peninsula , planning the rest of the trip kinda took over but will now look at this option again so thanks for the help.

  4. Default

    If you are any near the Marine Corps Musuem near Quantico off of Rt. 1 near Triangle, VA that is a must see. The museum is really great and it is free, no parking fee either.

  5. #5


    Thanks yes spotted it when researching this trip, We visited the National WW1 Museum in Kansas City, Mo a couple of years back & were very impressed so its on our to do list if we take that route, thanks again.

  6. #6
    Join Date
    Apr 2013
    Oakville, ON, Canada


    With respect to old diners, there is the Triangle Diner in Winchester, VA which has been in business since 1948. I have never been but found it on, a website I had stumbled across months ago that has an extensive list of diners (both operating and not) in every state. You can see if there are any others along your route. If you have time, Virginia Beach is a little over an hour from Williamsburg. It is an easy side trip from Williamsburg. We stayed there about 10 years ago and loved it. There is a 3-mile boardwalk and nice clean sandy beach. You can rent bikes and ride along the boardwalk.

  7. #7


    Thanks wec67, will check out both triangle diner & the website you mentioned, when doing these trips we always try to use mom & pop type of places or diners that have been in the same family for years & not the big chains, getting harder though so many are being lost, real shame ! have seen some stand out places for a Philly cheesesteak while in Philly & Bens chilli bowl in DC, & yes I keep looking at Virginia beach, from what you say I will try to go for sure thanks again.

  8. #8


    update on last post, just checked out the website & looks like we are a year too early! the Triangle diner is currently undergoing major restoration & hopes to reopen mid 2014, looks like a great place though & just the kind of place we love to visit, guess at least its good that they are investing so much into a sympathetic refurb , thanks again !

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