Um, that would be West Street Grill in Litchfield, CT

Keep those ideas coming! I'm going to present all of them to my friend this weekend so we can finally make a decision.

New England would be a great destination. Personally, I would vote for New Hampshire and Vermont to get the scenery you have described.

Keep in mind that flying to New England will use up at least half a day each way, so you will end up with at best 4 days (arrive NE midday on Day 1 and leave afternoon of Day 5) and at worst 3 days (arrive evening of Day 1 and depart morning of Day 5) of actual visiting.

I agree with the suggestion of Maine. The coast of Maine, especially Acadia, is the most scenic area in the country east of the Mississippi River. I have traveled extensively. No place else comes close.

Gail and laborman have the right idea, I summer in Maine (I'm v. fair) and you can spend a whole day in the sun and not get over exposed with sun (with proper coverage. More importantly, it's a beautiful area to visit and with so much coast, you really can go places where you feel like you have it all to yourself!! To see the best scenery and have the place to yourself, be sure to get off the beaten path. By all means see Acadia, but be sure to spend some time in the other coastal areas; Blue Hill, Deer Isle, and further north way downeast, at Schoodic and Cherryfield.

Fly into Hartford (BDL), take RT 91 north to Greenfield, MA. Take rt 2 to western MA, Rt 7 north to Bennington, VT. Continue on to Manchester, VT. Take Rt 30 north to Middlebury, VT. Rt 125 to Rt 100 S to Killingon Mt.
Rt 4 west to Woodstock, VT. You will see some magnificant scenery and almost more history than one can stand.
From Woodstock, I would head north on Rt 12, then east to NH. South on Rt 89, and return from Manchester, NH.
Excellent trip, with many excellent restaurants and places to stay along the route.
Let me know if you want more specific info.
Happy Traveling !!!

I'm going to also plug New England. Specifically, fly into BOS or Manchester and drive Western Mass. A $10 ticket at Tanglewood will get you lawn seating where you can picnic while listening to one of the best symphonies in the US. Take a cooler with your favorite wine and a cold dinner.

I've stayed at The Inn at Green River just over the border in Greenhill, NY (www.innatgreenriver.com) a couple of times -- it's a great farmhouse-type inn, and the owner, Deb Bowen, is a treat. Lots of wonderful towns filled with restaurants and shopping in the area.

You can also drive further west 30 minutes to the town of Hudson, on the Hudson River. It used to be a prison town and now has a wonderful downtown filled with art and antique shops. South of town is Olana (www.olana.org), the newly restored mansion of the American landscape painter Frederic Edwin Church; a wonderful tour with amazing views of the Hudson from its hilltop setting.

Maine! Specifically the town of Lincolnville. Lincolnville - just north of Camden - has everything, including endless photo-ops. Some examples...an island dotted Bay, a pristine lake with Loons, mountains that seem to flow right into the ocean, great places to stay and eat, a ferry to an island, and quaint without kitsch. Acadia is beautiful and makes a nice day trip!!

BTW, JetBlue has 3 daily, direct, 2 hour flights to BOS from Charlotte, NC and numerous longer flights that connect through JFK. It's about a 2 to 2.5 hour drive from Boston to the Berkshires and Green River, NY (sorry, it's not Greenhill, had the name wrong) in non-rush hour traffic. In rush hour traffic along the MassPike, it's anyone's guess, so watch your arrival and departure times if you decide to fly to BOS.

Hi! Just to throw out another itinerary - fly into Burlington, VT (gorgeous town on Lake Champlain with lots of history and the scenery is breathtaking), drive to Montreal (only about 1 1/2 hours), tons of history and a beautiful french city. Then from Burlington again, go south down I-89 to Ben & Jerry's; the village of Stowe where the Trapp Family Lodge is (yes, the Sound of Music family); then go to Cabot (the cheese company). There are so many other things in that area - if you check out this website or AAA you will be set! My husband and I did this a few years ago, and just went wild for that area. We're from Memphis, so it was very different for us!

Oh, one more thing - no rush hours or traffic jams to worry about up there!

The Shenandoah area of Va is beautiful as is the Charlottesville ....president's homes (Monticello, Ash Lawn), history and mountains. Pretty town...wonderful. It is also a beautiful drive going up there.

Also, adding on to my previous reply, Charlottesville is just a short hop away from DC.

What dates in June are you traveling?

In New England, some points of interest (like museums, historic houses, and such) do not open for the summer until late in June (or even July 1). If a certain attraction really catches your interest, make sure it will be open before you plan your trip around visiting it.

We're looking at mid-June...around the 14th or so. Thanks for the info about some places in NE not opening until later...I never would have thought about that. If we decide on NE, I will definitely check out the opening dates of any place we're interested in!

I'd vote for Virginia as someone earlier commented. It's close to you and has all that you're looking for - as well as things you said you didn't want. Start with a trip to Colonial Williamsburg - the country's largest outdoor living history museum. While there spend a day visiting Jamestown and Yorktown where British America began and ended. Then drive up into the mountains two hours away and visit Charlottesville and the Shenandoah Valley. You can even drive back south toward home on the Skyline Drive and Blue Ridge Parkway. You'll have all the history and beauty you can handle in five days.

Have fun wherever you end up going!

What's the weather like in Virginia in mid-June? I haven't been there in over 40 years, so that's a definite possibility.

Regarding you inquiry about Upstate NY, i am surprised no one replied. Allow me to give you a list. Upstate NY is quite diverse and very lovely, many photo ops. From east to west, Hudson River, Vanderbilt estate, Roosevelt's home, Culinary institute, West Point Miltary Acadamy,Catskill mountains, Cooperstown; Baseball hall of fame. Lake George, (Lake Winnepausake, Actually in Meredith NH, but quite lovely) Adirondack Mountains, Lace placid, (You remember the Olympics.Finger lakes; wine country, Watkins Glenn, Letchworth State park; Grand canyon of the east. Rochester; Home of Eastman Kodak, Corning Glass works. Niagara Falls, Lake Ontario. I am sure a left a few things out . And don't forget our other world. NYC.