I live in California and want to fly to the east coast, rent a car and drive through the countryside, stay at small Inns and see the gorgeous fall colors that I've only seen in pictures. I'd like to enjoy the local cuisine as well. Where should I fly into to begin and then to fly out of at the end. I will only have 4 nights/5 days and a total budget of approx. $1,800. Can it be done for this amount of money? By this late September or early October?
To accomplish this for the upcoming fall season, I would advise you to make your travel reservations as soon as possible. Flying into and out of Boston is usually the most affordable option, although you may consider price-checking Southwest's and other airlines' fares for Manchester (New Hampshire), as occasionally the rates can be comparable. Flying into Manchester also slightly reduces your driving time to prime leaf-peeping areas and lets you avoid the potentially more stressful driving in Boston.
Where to go in order to see the best colors will depend on the precise timing of your trip as well as the weather conditions that influence the color progression, which varies from year to year. The Foliage Network is a good resource for planning your scenic drives as it provides a map of the real-time color progression updated every 3-4 days. That said, the maps are somewhat imprecise so it may often be more helpful to rely on local word-of-mouth to find the prettiest drives. The Vermont Department of Tourism website provides real-time crowd-sourced foliage updates, which can be very helpful for planning drives in that state.
Generally, the most vibrant colors are found in areas dominated by northern hardwood forest. These are the areas colored orange in the map below. This doesn't mean you won't find beautiful colors elsewhere in New England, only that these places are typically your "best bet." These areas also tend to be more hilly/mountainous, providing sweeping vistas of the foliage.
As you can see from the map, some of the best foliage-viewing areas in New England are western Maine, northern and western New Hampshire, most of Vermont, and western Massachusetts.
The color changes progress from north-to-south, inland-to-coast, and mountain-to-valley. One of the reasons why New England is a good leaf-peeping destination is because the drive between mountains and coast is relatively short, so if the colors are past peak in one area it's usually easy to find peak color nearby.
The last week in September is the absolute earliest I would recommend arriving for a foliage trip. You're unlikely to see much color before this time, especially if the weather is warmer than average. The last few days of September and first few days of October are typically the ideal time to see color in the beautiful and unspoiled Rangeley Lakes region of Maine, including the stunning views at Height of Land and Grafton Notch State Park. The sleepy villages of Andover and Oquossoc are good bases for exploring this pristine, mostly tourist-free, area.
Just across the border in New Hampshire, you will find breathtaking color the same time of year in Pinkham Notch, along Route 16 north of Gorham, along Route 302 between Bretton Woods and Twin Mountain, and continuing along Route 3 to Franconia. You will find plenty of small town charm in places like Gorham, Bethlehem (New Hampshire), and Sugar Hill. Two other fantastic foliage drives in the White Mountains are the famous Kancamagus Hwy and the less-traveled Bear Notch Road, which tend to hang on to their colors longer than the areas mentioned above, often through the first half of October.
A great spot for early season color in Vermont is Groton State Forest and the beloved view at Kettle Pond State Park. This area is chock-full of quaint New England villages, including Peacham and Cabot (on a clear day, check out the views of both the White and Green Mountains visible from Foster Bridge). A bit further north, the crystalline waters of Lake Willoughby and the expansive views from Burke Mountain may be worth a detour. To the west, Smugglers Notch is a very scenic drive in early fall, and nearby Stowe is a popular base for leaf-peeping excursions through the first couple weeks of October. (Although Route 100 can get busy, Stowe Hollow Road runs parallel and is arguably more scenic).
If you are arriving in the region a bit later, say, around the second (or maybe even third) week of October, you may have to shift your itinerary slightly further south in order to see the best colors. Western Massachusetts has some scenic gems, like the incredibly well-preserved village of Deerfield (Massachusetts) and the nearby vista from Mount Sugarloaf State Reservation. Route 2 (the Mohawk Trail) is a great foliage drive, especially between charming Shelburne Falls and Williamstown (Massachusetts). You might also consider a drive to the top of Mount Greylock or a visit to Hancock Shaker Village.
It's honestly hard to go wrong in the southern half of Vermont in terms of finding beautiful places - historic Bennington sits at the junction of VT Route 9 and US Route 7, both great foliage drives. Route 9 is quieter but tends to peak early (like Route 100), whereas Route 7 is a highway that usually has stunning colors into the middle of the month. From Manchester you could head east to any number of quaint Vermont villages (my personal favorite being Grafton (Vermont)).
Southwestern New Hampshire (the Monadnock Region) is a beautiful and well-preserved part of the state that is crisscrossed by two of my personal favorite foliage drives, the highway-like Route 9 and the idyllic Route 123. Keene is a lively and charming base for this area, while Harrisville and Hancock are quiet villages teeming with history.
To the northeast, New Hampshire's Lakes Region is also a good spot for mid-October leaf-peeping. If you're up for a hike, Cardigan Mountain in Cardigan Mountain State Forest is a personal favorite this time of year. Drive along the western shore of Newfound Lake for an off-the-beaten path foliage drive. Another local favorite is Old Bristol Road. Route 113 between Holderness and the ridiculously quaint village of Sandwich is a good one too (stop for the popular view at the short-and-easy hike up Rattlesnake Mtn). Consider heading further east along Route 113A to the equally idyllic Tamworth.
The Castle in the Clouds is a well-loved Lakes Region destination worthy of an extended visit, and routes 109, 109A, and 28 offer nice views along the eastern side of Lake Winnipesaukee. Charming Wolfeboro has one of my favorite bike trails in the region - consider seeing the colors by bike if you want to take a break from driving.
Further north, route 302 from Bartlett up to Crawford Notch State Park always has beautiful colors that tend to hang on a bit longer than other places in the White Mountains. A word of warning, however - if you are traveling during Columbus Day Weekend (October 6-9 this year) you are likely to encounter considerable traffic in key "chokepoints" like Conway/North Conway, Lincoln, and Meredith. For Conway/North Conway, you can use West Side Rd to bypass the worst of it (and thankfully there are a couple of nice state parks to visit along this road).
If I am leaf-peeping on Columbus Day Weekend, I prefer to go off the beaten path on those days. Another crucial tip: wake up early! I can't stress this enough. The sun rises and sets early in New England (compared to most of the US), and fall days are short. You'll get the most out of your trip if you maximize your daylight hours, and many areas are more serene and tourist-free in the early morning.
Again, the timing of the colors varies year-to-year so it's helpful to have some flexibility in terms of where you drive each day. Remember this general rule of thumb: if you see mostly green around you, head north, west, and/or to higher elevations. If you see mostly brown around you, head south, east, and/or to lower elevations.
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Ballpark for a plane ticket would be $500, so that allows $1300 for the car, gas and hotels and meals. I'm thinking that the cheapest place to fly into would be Boston Logan International Airport Car rental websites advertise $10/day from there, but I'd allow $200 for the car and gas. That gives you about $200/day for hotels and meals. I don't know how many small inns you can stay in, or magnificent meals you can eat for that price, but you can definitely see some fall color.
We drove from Maryland up to Vermont after Columbus Day, and the foliage in Vermont was spectacular, but I think it is usually a little earlier than that. Just before you go, look at some of the websites which have the amount of fall color for various areas, and set your path for those areas which are reported as peak color. It is different every year. So if it is a warm green year, go north to Maine and western Vermont in the mountains for fall color, and if it has been cold and many trees have already turned, you can go to western Massachusetts or Connecticut.
I only know about one day when we drove through upstate Vermont. We saw lots of pretty trees, and had two marvelous dinners at Fire & Ice (but I have to put a disclaimer in here - our grandson is the head chef there).
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I highly recommend to visit @gunstock located in @gilford, @newhampshire. A beautiful resort on the top of the mountains where you can admire the forest and where the peak of the fall can be beautifully observed.