If you are interested in "quaint villages" I would not recommend Stowe which is very touristy.

You might want to look at the Highland Lodge on Caspian Lake in the NOrtheast Kingdom (Greensboro).

We are really looking forward to our upcoming May trip thanks to all who have been so generous with their suggestions. Our Vermont packet with a great map arrived and we are narrowing down our tour to:

Two nights in Waitsfield at Round Barn Inn. Questions -- can we see Shellburne Farms and tour Burlington area in that time frame? What about the weather for a little hiking by Round Barn Inn in late May?

Two nights in Woodstock. Yes, we opted for a 4th night. We have looked at online sites for Jackson House Inn and Kedron Valley Inn. It does seem like there is a lot to do there. Is Jackson House in town? Is there hiking nearby?

We will definitely try to locate most of the restaurants that you have recommended and certainly plan to visit the Vermont Country Store. Most of all we hope to capture some of the essence of Vt by lingering in your quaint villages.

Any further suggestions and answers to our questions would be appreciated.
Kitty and Bob

Some people spend not only a full day but also a second day at Shelburne Museum. We spent a good part of the day and had lunch in the museum cafeteria. If you don't mind a long day you could go to Burlington for dinner before return to Waitsfield. Shelburne Farms and Shelburne Museum are two different places. I assume you meant the Museum which is spread over several acres and several buildings plus a full size steam ship that used to be on Lake Champlain. If you are gardeners you would want to visit the Intervale section just above Burlington. I think there are hiking and biking trails, maybe kayaking and Gardener's Supply store and demonstration gardens.
Unfortunately, late May is putting you in prime black fly season so hiking in the woods may not be a good idea. There might be a black fly map for the state which gives you an idea for the times when they would be at the worst. They won't be a bother in towns just the woods and some years they aren't so bad. It depends on the amount of rainfall and a person's natural sensitivity. They seem to find some people especially tasty. If we get a cold spell they might not be out. There's plenty to do if you can't hike. They shouldn't be a problem on the grounds of the museum. I also recommend Simon Pierce for lunch. Get there early and get a seat as soon as the restaurant opens and you might be able to get a table overlooking the rapids. They generate their own electricity. There are potters and glass blowers you can watch and see pictures about the hydro electric. The food is gourmet.

A site that should be helpful for the Woodstock area is www.woodstockvt.com. It has lots of good information, including weather, reastaurants, lodging, hiking trails and all sorts of activities. In answer to your question about the Jackson House Inn, it is located a few miles west of town, just off Rt. #4. If you want to stay in town, there are other B&B's, though I have no first hand knowledge. You might try Trip Advisor to see what others say.

Good choice with the Inn at Round Barn -- your should love it! The Waitsfield area is about 45 minutes from Burlington, an hour from Shelburne.
Day trips over there are certainly doable, depending on how much time you want to spend at the Shelburne Museum or Shelburne Farms. The Church Street Market Place, a pedestrian mall in downtown Burlington, has nice shops and restaurants. Leunigs Bistro on Church St. is one of the best restaurants in the city. The Burlington waterfront park is also worth a visit.

Another idea for a day trip, or route to head south to CT is to cross over the mountains from the Mad River Valley via Rt. 17. This is a beautiful drive that will bring you down into the village of Bristol. From there continue on 17 to Rt. #7, then south through Middlebury. I don't know where you are going in CT, but you can take Rt. 7 all the way down. Slow going, but very scenic, including Manchester, Arlington, etc. If you don't want to backtrack your Rutland-Brandon route, try Rt. #30 south from Middlebury, through Poultney and Dorset to Manchester - a lovely drive.

Let me know if you have any other questions! Have a wonderful trip!

Shelburne Museum can definitely take a full day. There are some amazing collections including one of carousel animals and circus figures and some great Impressionist paintings in addition to all the New England buildings.

Another interesting historic site in the Intervale area above Burlington, mentioned by another poster is the Ethan Allen Homestead
http://www.ethanallenhomestead.org/

We will drive to Essex, CT on Monday of the Memorial Day weekend. I know, our timing couldn't get any worse! If we leave in the morning can any of you suggest a good route to take to avoid crawing with traffic?

The best way to avoid crawling traffic is to stay off the back roads on a holiday weekend and opt for interstate highways. Assuming you are leaving from Woodstock, head east on Rt. 4 to Quechee and pick up I89 (which is a beautiful route anyway!) In White River Junction, intersect with I91, which will take you south through Massachusetts and into CT. Just south of Hartford, CT is Rt. #9, which will take you to Essex. The trip should take in the neighborhood of 5 hrs., depending on traffic and stops.

Another option, especially if you are staying at the Kedron Valley Inn, is to take Rt. 106 from So. Woodstock, to Rt. 44 east to Windsor, or all the way south on 106 to Springfield, VT, to pick up I91. This is not a long distance, will avoid backtracking on Rt. 4, and will give you one last taste of rural VT!

Definitely avoid Rt. #7 (I had suggested it in a prior post) Though scenic, it will be very slow going, and will bring you into CT far west of your destination.

If you are not in a hurry, Northampton, MA (right off I91) might be a good lunch stop for you. Home of Smith College, there is a selection of decent restaurants.

Colbeck gives excellent advice -

usually everyone else is on the highways/Pike trying to drive home as fast as they can -

take your time, do the back roads, stop and enjoy the views and meals along the way and you will have a delightful day -

oops and I just realized he gave the exact opposite advice that I did ! Oh well, as my Dad would say, that's what makes a horse race -

My experience has been tourists, family, etc usually jump on the highway - so we always take back roads, as we will home from Maine, as much as we can, on the same weekend. We will take our time and enjoy so any traffic does not frustrate us and stop it at whatever little spots are open -

sorry - guess it's a toss up -

listen to the traffic reports and/or bring a gps with you too !

KittyBob,
Escargot has a good point too -- in fact, we usually prefer back roads to the highways. However, it depends on how much time you want to spend getting to your destination.

On a holiday weekend in VT, roads like Rt. #7 will be stop and go. On the other hand, I89, though busier than usual, will be faster moving and not congested. However, once you get into the more populated areas of MA and CT on I91, the highway traffic will definitely increase, particularly in Springfield and Hartford.

Unfortunatley, I don't know enough about the back roads in those areas to offer any suggestions.

Guess it's up to you and your schedule!