most scenic route Arlington VA to South Lee MA
 

Our family of four (kids age 21 and 17) will be driving from Arlington VA (arriving from CA the day before) on June 24 to South Lee in western Mass where we will have a time share stay for six days. Following that we will visit Boston, NYC and the DC area. Coming back from NYC to DC we will drive the most direct route, but coming from Arlington to South Lee MA to start our trip we will have the whole day to drive, with no deadline or agenda, (just want to be at our timeshare by around 9 that evening.) I'd like to go on a slower paced, scenic route, with maybe visiting one interesting location on the way there, such as Gettysburg.

>>but coming from Arlington to South Lee MA to start our trip we will have the whole day to drive, with no deadline or agenda<<

It will take the whole day -- at least 7 hours without a stop by the most direct route. And probably longer because of crazy traffic. So with meals and rest stops it will be close to 10+ hours.. Is there a reason you are flying into DC if your destination is western Mass?

We are doing the extra driving because it amounted to a huge savings in terms of rental car price (for two weeks an instate return and drop off was much cheaper than renting in MA and dropping off in Maryland or VA or DC which is where we finish our 17 day trip at least for the rental car companies I checked) and we had flight vouchers for all four of us which worked better time and price wise to DC than elsewhere on the east coast anyway. My daughter loves all day road trips also.

>>My daughter loves all day road trips also.<<

Well, that's good since that's what you'll have. :) Unfortunately there wouldn't be time for any sightseeing, scenic detours, etc. . . . Unless you want to eat the first night of your timeshare and make a 2 day drive out of it.

Well, I've done all or parts of this trip numerous times. Not quite the same start/end points, but close enough.

It is a loooong way, ~7hrs direct drive on the interstate, with time added for gas/food/bio breaks, so the question to ask is not necessarily "scenic drive", but rather what route has some place(s) interesting to stop along the way.

Here are some ideas you can chew on.

1. My usual stopping places one way or the other include Ikea in Paramus and Woodbury commons in NY. I don't think shopping is what you mean. And there are outlets in Lee, so you don't need outlet shopping anyway.
2. Go through Gettysburg, Harrisburg/Hershey PA. This will add about an hour drive, plus more time for stopping at the battlefield. Bonus, you avoid NYC area traffic.
3. Cut across NJ towards Atlantic City, then north on the Garden State Parkway, and stop somewhere along the shore, eg Barnegat light, Island beach state park, seaside park (boardwalk), or Asbury Park. Would add about 2hrs drive. Definitely avoid this route on a Sat or Sun as you'll get stuck in beach traffic.
4. Find a place to stop once you are through NJ. West Point, Storm King art center, walkway over the hudson. Would add approx 30-45min to your drive, plus stopping time, give you a chance to see something but still get most of your miles behind you before you stop to sightsee.
5. If you want just an hr or some of a more scenic drive towards the end, then take the Taconic Parkway from I84 north, then meander through the Berkshires to Lee. This route would add about 30min to your drive. You could stop at a winery in Millbrook NY, or visit Innisfree gardens in the same town.

Numerous other options - these are just some ideas.

Last time from your area, we did the I78 route as far a Newburgh NY then I84 because we had to go back thru CT to drop off a friend. It's a shame Frederick MD is so close to the beginning of your trip because the Community Bridge is an outstanding thing to see and there's a lovely area of small shops to visit. Google the story behind the trompe l'oeil artwork. There are a few examples in the shop area. When we saw one window, we had an argument as to whether it was a real window or a painted one. Friends were voting for real but it was painted. So much fun.

Google maps recommendation to continue north toward Albany is probably good since getting thru Hartford can be dicey most times of the day and I wouldn't even consider it if it was rush hour.

I agree with others it would be very hard to add places to stop along the way and/or scenic driving and still make the trip from Arlington to South Lee in one day.
Gettysburg would be interesting but a long stop. If you want to go there, the drive north on Rte 17 in MD is pretty.

Here is a route that will take a little longer but be much more interesting and allow for some nice scenery. Go to google maps and put in:

Arlington VA>Gettysburg PA>Stroudsburg PA>Port Jervis NY>Lee MA

You could stop in Gettysburg for a while and visit the VC and Battlefield. From Stroudsburg to Port Jervis take 209 through the Delaware Water Gap NP. This is a pretty drive and has some places where you can stop and do a short hike to waterfalls (don't go to any that you have to pay to visit there are 2 or 3 that the NP controls.

You don't need to go to Port Jervis get on 84 when you get to it, I just put it in there to make the map take you through the water gap.