Vermont itinerary help
 

I'm trying to plan a trip to VT in the fall (Columbus weekend) and am hopelessly confused.

We're flying in to Burlington and so far have booked one night in Waitsfield followed by two in Woodstock. I have another two nights after that before flying back to NYC from either Manchester NH or Burlington VT, whichever works out nearest

Does anyone have any suggestions for what is unmissable and where we should spend those two nights? Apart from that, what should we be doing in the days?

For Columbus Day weekend there will be several fall foliage festivals and country fairs going on. I like the one in Warner NH because they have a craft fair, farmers market and parade. It's a lovely town nestled up against Mt Kearsarge which would also provide some hiking opportunities. It's also probably only an hour from Woodstock via Rt 89. Vermont is very beautiful, well known for rolling fields and hills but you need to go to NH for the craggy granite landscape of the White Mountains ... and again it's very close to Woodstock which is near the VT/NH border. The bad part is there's going to be a lot of traffic in the mountains during the 3 day weekend so I would save the mountains for a weekday. There is probably a lot less traffic along the CT river where you'll find some quaint towns. You could also easily fit in a day trip to the seacoast since Portsmouth NH, for example is less than an hour from MHT. Burlington VT to Concord NH is about 3 hours. Concord is about 20 minutes north of MHT. Portsmouth is 45 minutes east of Concord. Great restaurants in Portsmouth, btw. If you want to be more focused in the White Mountains, they're only an hour north of Concord and in between is beautiful Lake Winnipesaukee. (Think foliage train or cruise.) It really depends on how you want to spend your time. If the weather is good you might also find some places still renting kayaks. Do you want to eat at great restaurants (i.e. Simon Pierce in Quechee near Woodstock) or local places, good but not pricey? Do you want to hike or bike? Do some early holiday shopping? I like to get some local apples and fresh cider. Maybe choose lodging in the White Mountains based on recommendations.

dfnh has some great ideas for you -- and also made a good point. What types of activities are you most interestd in? The Woodsotck area is a good choice, as there are lots of things to do there. If you could give us a better idea of your preferences, we could be more helpful with additional suggestions.
Keep in mind, Columbus Day Weekend is the absolute busiest of the year in Vermont and most parts of New Hampshire, so be prepared for traffic and make sure you have reservations.

We have stayed in Quechee and enjoyed it. Small town with Quechee Gorge there. Also, Stowe is lovely anytime of the year.

Agree with Stowe suggestion. I would do that first out of Burlington.

Thanks for the suggestions! I love the idea of a foliage cruise/train.
I'm going with my mom who's not brilliantly mobile, so while short walks are good, we're not the most active of people

I think that eating and shopping will be incidental if we're in the area with any great places but what I'm most looking for are the unmissable sights/attractions.

Our current updated route runs to

Burlington --> Waitsfield --> Woodstock --> Lake Winnipesaukee --> Lincoln --> Craftsbury Common --> Burlington.

Is that feasible in 5 nights and are there any other places in the area that I'm missing or have I included places that just aren't that worth taking the time to see?

We've made a couple of reservations already (the round barn farm in waitsfield and the woodstocker in woodstock) but would love any recommendations for other places on the route.

Thanks again!

You could certainly plan on two days in Woodstock. There is so much to see there. Don't miss the Rockefeller Mansion tour. This lovely estate is a National Park. They give guided tours of the building and grounds. Also of interest in Woodstock is the Billings Farm and Museum. This farm, established by the Rockefeller family is a recreation of a VT turn of the century farm. Definitely worth seeing.

Since it's so close to us we've never stayed in Meredith on Lake Winnipesaukee. There's several lovely hotels in the downtown area plus shopping/restaurants within walking distance. The only bad point is the traffic congestion at the lights. To get the foliage cruise or train you would go south to Weirs Beach, a popular arcade type of area. It's a short drive, just expect it to be slow. The Meredith hotels would have a lot of rooms looking out on the lake. You would have a pleasant area to walk without it being too far. Going further northeast around the lake our favorite drive any time of the year is Center Sandwich. A very old town. Also you are near Squam Lakes (where On Golden Pond was filmed). However the Sandwich Fair is running the 3 days of Columbus Day weekend so there will be a lot of traffic in a very small town. If your dates don't coincide, that would be great. This is one of the loveliest areas of NH, settled in the early years and not built up although just a few miles a way there's lots of cottages, stores, etc built up around Lake W. You're not in the middle of the mountains but almost. On two occasions we have seen black bears next to the road. There's a small country doctor/farm museum in Tamworth. We haven't been on a tour but it's another interesting old town and I see interesting weekend activities held there. We have enjoyed dinner at the Corner House Tavern in Ctr Sandwich. If you like ice cream the Sandwich Creamery sells their own and it's a challenge to find them since they are in the middle of nowhere. See their website. The recently retired head of NH Dept of Agriculture listed Sandwich as one of the top 100 places to see in NH. It's just a tiny bit off the beaten track. Wolfeboro would be my second choice of a place to stay but it's on the other side of the very big lake from the cruise and train.
Yankee Magazine has a website and also publishes a guide to visiting New England which might be very helpful to you.

With 5 nights, you might want to consider 2 nights in either Waitsfield or Woodstock, since they are within an hour of each other. Which to choose is the question - the Round Barn in Waitsfield is in a VERY beautiful 'ultimate Vermont' setting. Woodstock on the other hand is a small, bustling village with lots of charming shops and restaurants. Lincoln is the gateway to the spectacular Kancamangus Highway, which will often have moose grazing near the road. Lincoln itself however is quite commercialized and developed compared to places like Waitsfield.

zootsi has a good point -- two nights in either Waitsfield or Woodstock. In fact I am always in favor (I know it's not always possible)of staying at least two nights in each place, especially when there is so much to see and do. The Inn at Round Barn is very special, and in an incredibly beautiful setting. From there you could take a day trip to Stowe by way of scenic Rt. 100. The village of Stowe is charming, with shops and restaurants. The road to the mountain has a lot to offer as well. There is an excellent Fall Foliage Art and Craft Show on Columbus Day weekend If it's a good day, you might take a gondola ride to the summit of Mt. Mansfield. Take a look at www.gostowe.com to see what the options are.

On your way to New Hampshire you could make a stop in Woodstock, perhaps at the Billings Farm Museum, or in the village for a brief walk around. An excellent place for lunch is Simon Pearce in Quechee. The restaurant is located in an old mill on the Ottoquechee River that houses the Simon Pearce glass blowing studio and retail shop. The restuarant is very popular, so advance reservations are advised.

In New Hampshire, I agree with another poster that Lincoln is not the place to stay. If you are looking for sights, the cog railway trip up Mt. Washington is fun, and the Mt. Washington Hotel in Crawford Notch is lovely. It's one of the few remaining grand old hotels. A gorgeous drive from there would be taking Rt. 302 through North Conway to Rt. 112 (Kancamagus Highway)to Lincoln, then back up Rt. 3 to Breton Woods, where the hotel is located. Lots to see along the way -- slow going, but worth the time.

The trip to Craftsbury Common from Breton Woods is fairly short and quite scenic. CC is located in the Northeast Kingdom, which is quintessential Vermont. If you opt not to visit Stowe from Waitsfield, you can drive through there on your way back to Burlington. There are some great places to stay in Stowe as well, such as the Green Mountain Inn, which is in the village, or the Trapp Family Lodge, which has a gorgeous hilltop setting.

Hope I haven't confused you even more! Have a wonderful trip!