VT from Boston in 5 days
 

I am flying into Boston on 7/23 and out on 7/28. I'd like to drive north and see some of VT, without trying to do too much. Any suggestions on a towns to overnight in and stops along the way? I was considering first night Woodstock, second two nights Burlington (?), then unsure, but the fifth night needs to be Boston, as we fly out early. Just hoping to see some natural beauty, eat well, etc.

I am partial to that area of Vt, spending many long weekends there when my daughter was in college in Middlebury - Woodstock is delightful - then you could drive on 4 and 7 to Middlebury ( or skip Woodstock and go straight Boston to Middlebury - :)

either way, it's about an hour from Woodstock to Middlebury - it's a great area -
the mountains, the Breadloaf school ( read about Robert Frost/ this area) - and the college town of Middlebury has some great quaint areas, the Frog Hollow art ctr, the falls,
and if you continue on 7 to Burlington ( about another hour) you pass everything from the Soapworks, to Vermont TEddy Bear factory, to the Henry Sheldon Museum, Lake Champlain, covered bridges, art studios, farm/knitting studios, blacksmiths, galleries, the vermont wildflower farm, (great restaurants: starry night cafe is one) and on into Burlington which has a great downtown and fabulous restaurants and events - Noonie's in Middlebury used to have fabulous sandwiches, Otter Creek Bakery always a good choice -

if you stay in Middlebury a night, look at the Middlebury Inn, Swift House or Waybury Inn

good web site ofthe mid vermont area: www.addisoncounty.com

You will find that the western side of VT has a lot of beautiful farm country between Middlebury and Burlington. I agree that Middlebury would be a nice place to stay. Nice little shopping area, pedestrian bridge over the river, etc. You might consider heading from Boston toward Nashua NH, then taking Rt 101 over to Keene and then Brattleboro to Bennington and then heading north to Middlebury. Once you leave Nashua you will go thru NH's quiet southwestern corner. Peterborough would make a nice place for lunch, an artsy community on the river. We love the Toadstool Bookstore since it has both new and used books. Brattleboro to Bennington takes you over a mountain but it's not very tall.
As you head to Middlebury you might want to check out Brandon VT. North is Bristol. If you take a slight detour on the Lincoln Gap (pretty drive) just outside of the town of Bristol is a very popular swimming hole. At one place on the river it is very shallow. You can walk across if you have water shoes. Just a bit upstream there is a small waterfall, deep pool and ledges. The older kids jump off the ledges. You can get a cool seat in the shade just to watch.
If you decide to stay in Burlington you can make a visit to the Gardeners Supply store north of town. There are demonstration gardens, bike paths, etc. For quiet beauty you can head north almost to the Canadian border and then take the southern route thru the islands. You will not see very much commercial activity but if you get an early start you can easily be back in Burlington in time for lunch. The Shelburne Museum between Middlebury and Burlington is great.
Some people spend more than a day there.
I would save Woodstock for the trip back to Boston since it's an easy route via I89 to I93 to Boston. Do not miss Simon Pierce for a great dining experience or at least explore the building (they generate their own hydro-electric power). Woodstock to Boston is probably about 2 1/2 hours.
A lot of towns in New England have free outdoor concerts on certain nights. Check events. Generally people bring a lawn chair and a picnic lunch and get there about an hour early. DH likes to take the ferry ride from Burlington across Lake Champlain just because he likes ferries. We usually have lunch at the cafe on Church St in Burlington run by the cooking school but it's been a couple of years since we did that.

I second the Shelburne Museum complex outside of Burlington. It's a complex of buildings and collections of Electra Havemeyer Webb (of the Domino sugar Havemeyers). If you stay in Burlington, there is a hotel whose rooms face Lake Champlain - unbelievable sunsets. It used to be the Wyndham. A great breakfast place in Burlington is Penny Clus. Lake Champlain chocolates are great.

What great ideas, thanks. We don't get into Boston on Thursday until 5 pm,I don't think we'd want to drive all the way to Middlebury on the first night. Could you suggest where to sleep the first night? Then, would one night in Middlebury and 2 in Burlington be good spacing to see the area? Maybe then we could just hit Woodstock for lunch on the way back to Boston on Monday. With an 8 am flight, should we just stay near the airport? I have fears about the Boston traffic. Thanks in advance.

Brattleboro is a cute town in the south east corner of the state and only 2 hours outside Boston.

Yes, I think that would work well. I now have a reservation at the Latchis Hotel in Brattleboro for the first night, my husband love old movie theatres so I think he'll enjoy it.

Running into problems...there are NO rooms to be had in Middlebury for Friday night. Any suggestions on other towns to lay one's head on the way from Bennington to Burlington?

<< We usually have lunch at the cafe on Church St in Burlington run by the cooking school >>
dfrostnh - we used to like dinner there, but they closed in 05 or 06. There's another location, I think, outside of Burlington.

There are many places to eat on and around Church Street.

maybe try for rooms in Vergennes? or Killington ? Ripton> or maybe head to Burlington .....
wonder what is going on - probably a Breadloaf something or a language school / etc?

Try Brandon VT. It's a pretty little town. We haven't actually stayed there, we camped nearby.

I found a room at the Dorset Inn for the night, which looks nice. Thanks for all your help! Any other ideas for things to do are appreciated. Now, we're staying 1 night in Brattleboro, 1 in Dorset, 2 in Burlington and 1 in Boston.

Some lunch ideas for you on your trip up Rt. 7 from Dorset to Burlington. In Brandon there is the Cafe Provence on the main street (right side). Just north of town is Cattails, which is simple, but good food. If you make it to Middlebury by lunch time, try the Storm Cafe, which is in an historic stone mill at the foot of the falls - excellent food in a scenic location. They have an outside deck if the weather cooperates. You can take some time strolling around town aferwards. Sorry there were no accomodations available.... There may be several weddings that weekend.

Where are you staying in Burlington? Make sure you visit the waterfront area and Church Street Market Place. Splash on the Burlington dock is a fun outdoor spot for lunch. Anther good restaurant is Leunigs Bistro on Church Street.

Traveling south toward Boston, a stop in the Woodstock/Quechee area is well worth a stop. Simon Pearce is Quechee village is a delightful place for lunch. It is located in an old mill looking out over the river. Simon Pearce is an Irish glass blower, and there is a wonderful gallary and store there as well as the restaurant.

Another idea for you - instead of driving up Rt. 7, take Rt. 30 from Dorset to Middlebury. You will avoid the Rutland traffic and pass several lakes. It will take you about 1 1/2 hrs.

"In Brandon there is the Cafe Provence on the main street (right side). Just north of town is Cattails, which is simple, but good food."

I second both of those for good food, albeit somewhat different "styles", if your schedule allows. We've enjoyed both several times.

Thanks for your responses! We leave tomorrow and will definitely take Rt. 30 from Dorset. We are staying at the Courtyard in Burlington.