Portland is a great foodie city but on the way I would recommend a stop in Portsmouth NH for an inland rivers foliage cruise. Keep in mind that Columbus Day weekend is THE heaviest traffic weekend of the entire year. I would avoid the White Mountains during the weekend. Color will start soonest in the north so perhaps start with the White Mountains. The other reason why I would start with the White Mountains is that once you get far enough north on I93, say the NH/MA state line, it's heavily wooded so you should see some decent early color and it will get better the further north you go. I actually prefer I293 over staying on I93 because I like going along the river with the view of the old Manchester NH mill buildings. It's too bad the Concord NH view northbound to the west is the back of a strip mall but the Merrimack River is on the east side of the hwy. At certain times of day, there's a nice reflection of trees in the water. You will notice that you are starting to see distant hills/mountains. The scenery gets better and better until I93 actually cuts thru the mountains.

That said, I'm not a big fan of the White Mountains. People will recommend the Kancamagus Hwy. If you stay along the I93 corridor (for views I would choose Meredith/Inn at Mill Falls but I've never stayed there) you can go east over the Kanc and then return by heading south on Rt 16 and then thru Tamworth and Center Sandwich which is my very favorite route in any season.

I haven't been to Pittsburg in ages and then it was for snowmobile trips. I'm not sure the extra drive is worth it for a chance to see a moose. Twice we have seen a bear in the Center Sandwich area so you might get lucky.

From the White Mountains, yes head over toward Stowe but keep in mind Stowe is another favorite destination for leaf peepers so I would avoid on a weekend. The road between Stowe and Montpelier will be packed with tourists since that's where Ben and Jerry's is located.

You can get wine, cheese, ice cream etc trail maps for different New England states. Visiting some of the places will help you get off the major routes and to interesting locations. The Sandwich Creamery (see their website) is a little adventure. Rt 100 in VT is very wooded so we prefer the hwy on the western side of VT that runs along Lake Champlain with good views of farmland and foliage.

If you have to choose between VT and ME, I would choose Maine just for the ocean and lobster. There is too much to see so I would skip CT.

Add something to do to your trip besides looking at leaves and driving too many miles.

You asked about flying into BOS or MHT. I much prefer MHT! It is smaller and very easy to navigate, pick up my car, and get on the highway north. I'm flying into MHT on Oct 5 for 5 night visit. I'm booked for N. Conway and Concord NH. I've done this trip almost yearly since about 2005.

The Kancamagus is a great drive! I do it every year. There are many photo ops along this route. It will have some pretty heavy traffic that weekend, but it's still a fave of mine.

Your trip sounds a little bit rushed to me. I'd cut out at least one destination. I hate to change hotels almost every night. I prefer to base myself in one location for a few nights and explore that area. For me, N. Conway is perfect.

You will want to book your hotels as soon as you have your schedule figured out. I'm already booked, and have been for at least a month or more, and I don't arrive until October. The hotels do fill up!!

Carol

If u choose Rangley stay at the rangley inn drive south to Bethel maine take rt2 over to Gorham than South to Jackson NH (7 mi north of N Conway. Take the Cog RR top of Mt Washington. Pittsburh is just to remote IMO. Back to Manch via the Kanc

Thanks for the great information! Very excited about this trip. Am booking air to MHT. I will happily accept any ideas for lodging and "not-to-be-missed" restaurants. We're foodies! ... Appreciate all
the comments.

ohoh, you are going to go crazy if you visit the northern New England section of chowhound.com. You can do a search on any of the towns you plan to visit. Expect a lot of posts on lobster in Maine. Manchester NH has some really good restaurants. Brattleboro VT has one of the best farmers markets where you can buy ethnic food for lunch OR visit the Humble Kitchen food truck in the downtown area for Vietnamese sandwiches and pho.

It's getting late in the apple season but you should find some good orchards that still have some unusual varieties (i.e. Gould Hill in Hopkinton NH). In NH you can get a free copy of the weekly Hippo Press which has a good listing of restaurants and food events. Some places have regular wine tastings. It focuses on the Nashua, Manchester, Concord and Portsmouth areas.

If you get to Center Sandwich, the Corner House is a quaint place to eat. I haven't been there in a couple of years though.

So I'll nominate Pizza on Earth in Charlotte VT as the most unusual place to get pizza ... if you can find it (they also don't serve every day).

Jeff knows foliage better than anyone. Check out some of his photos for ideas of where to visit.