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jeverett May 10th, 2020 09:09 PM

New England autumn itinerary after Columbus Day
Hello Fodorites, I hope you are all doing well and staying inspired for future travels.

Last year my wife and I spent Columbus Day weekend in Portland, then road-tripped back to Boston via the White Mountains and lake country in NH. God forbid the status quo continues into the autumn months, but we are planning a return trip for our 10th anniversary. Maybe this happens or maybe it doesn't, but we need something to look forward to.

We enjoyed our three day trip so much last season that we decided we want to return and cover some new ground and spend longer. We're thinking of flying into Boston again over Columbus Day weekend, and spending the following week or so exploring New England, tentative dates Oct 9th - 19th.

My biggest question is what parts of New England typically have the most vibrant foliage the third week of October? We were looking to take this trip after Columbus Day weekend to avoid the expensive hotel rates and crowds.

One proposed itinerary we were considering is arriving in Boston on Friday, Oct. 9th, renting a car, and driving to Brattleboro, Vt. We would base ourselves there for three to four days (exploring the area and taking scenic day trips). Then head south through the Berkshires into Connecticut and staying two to three days there, seeing the Litchfield area before heading down to the coast to New Haven for a pizza crawl, then on to Mystic. Then over the weekend of Oct 16th-18th heading to Rhode Island to Newport, staying there for a couple of nights, and maybe taking a day trip to Providence before driving back to Boston and flying home on or around the 19th.

We are incredibly flexible on dates and itineraries, but mostly we were looking to find a good time where we could still enjoy fall leaves while taking advantage of offseason rates. I'm going to guess that the Brattleboro area gets busy over Columbus Day weekend, but would it be less crowded than, say, Stowe or Burlington areas?

We love exploring quaint New England towns, cider donuts and farms, some light hiking and beautiful walks, history, art, seafood!!!, and just getting off the main tourist track to see a more authentic side of things. If anyone has any ideas on other places I may be overlooking, or any suggestions on our itinerary it would be greatly appreciated. Thank you all in advance.

Michael May 11th, 2020 12:05 AM

I wuld base a little farther north in Vermont, perhaps Manchester or Woodstock. The colors develop from north to south, so central Vermont would give you the option to tour in either direction depending on the arrival of the colors.

oldemalloy May 11th, 2020 05:32 AM

While you are planning the trip, do look into flying into either Hartford/Springfield or Providence airports. They are served by the major airlines as well as Southwest and since you do not mention seeing Boston again, there is no need to deal with traffic there. Car rental might be less also.

Your general plan sounds fine and the colors in the far north are usually fading by the middle of October.

suze May 11th, 2020 06:43 PM

what parts of New England typically have the most vibrant foliage the third week of October?

Impossible to answer that question, since high "color" timing is a bit different every year, depends on weather patterns. I think Brattleboro is an excellent base (I used to live there, LOVE that little town!).

Fra_Diavolo May 11th, 2020 06:49 PM

Suze is right, but for what it's worth, Columbus Day weekend is usually the peak in Southern Vermont. Or at least it used to be. It's also not important to hit the exact peak. There's plenty of color before and after.

Vttraveler May 12th, 2020 07:40 AM

Here is a map that gives some idea of when different areas of New England have peak foliage

I live in north central VT and peak here is usually the last week of September/early October. Farther south would be better for the dates you are considering.

Usually it is hard to find lodging during peak foliage season, and Columbus Day weekend is especially bad, but who knows what travel will look like this year.

suze May 12th, 2020 08:46 AM

One easy but drive out of Brattleboro with spectacular views... take Route 9 from Brattleboro over to Bennington. It's only about an hour. Stop at Hogback Mountain gift shop midway.

Christina May 12th, 2020 09:11 AM

It must be the airline, but flying into Boston to visit Brattleboro doesn't make any sense to me. I visit VT a couple times a year, I have relatives there and I go skiing. I fly into either Hartford or Manchester NH if flying SWA, or Burlington if flying UAL. Actually, I've flown into Albany for SWA also when it fit my itinerary better, I think I was going to Killington first or something. Last time I flew into Hartford as it had much cheaper car rentals than Albany or Manchester for my dates. Brattleboro is a piece of cake drive from Hartford.

I've only been there during that time of year once or so, so don't have any opinion on that, but really like staying in Waterbury for convenience and good hotel rates. It's an easy drive from Burlington,obviously, but also Manchester as it's right on I81. I really like the Fairfield Inn and Suites in Waterbury.

I've flow in/out of Providence on SWA also but not to visit VT, but if your goal is VT then Providence, I'd fly SWA and forget Boston.

suze May 12th, 2020 09:23 AM

Ditto using Hartford as your airport suggestion. Would fit better with the end part of your trip as well. Boston is actually quite out of your way for the itinerary proposed. Excellent catch by Christina.

dfrostnh May 13th, 2020 02:18 AM

Some great suggestions. If you decide to go Bratleboro to Bennington, I would consider going further to Saratoga Springs, NY. I was surprised how much I liked it for a getaway weekend. We had a great food tour starting at a very vibrant farmers market. We also did a tour of Hildene in VT.
If you fly into MHT, there's a terrific apple orchard in Hopkinton NH very close to I89 Gould Hill Orchard. They also make their own hard cider. Then Rt 202 to Keene and over to Brattleboro.
A few years ago we did two Newport Mansions tours: one was Beneath the Breakers and the other mansion had a tour of the servants quarters. I liked these better than seeing that gold and gilt tours.

Hartford and Manchester NH aren't that far apart and neither is Providence. I think Manchester to Providence is less than 2 hour drive. I agree with advice to skip Boston. But, I think your dates for good weather might be a gamble. The weather is usually beautiful for the Columbus Day weekend period and then we get a spell of rain later in the month. If you avoid the overly popular tourist areas, you could come earlier.

J62 May 14th, 2020 03:24 AM

I'm in upstate NY.. Vttraveler, dfrostnh and I all live at around the same lattitude and share a common view of fall foliage.

A few more points from my perspective. Trying to hit picture postcard "peak" is a futile battle, with the biggest variables being weather, and crowds. The best leaves on the tree, but a rainy day is a waste. Same holds true for crowds. I'd much rather go a little later after crowds have thinned out, but it's still beautiful. While "peak" may be early to mid October, even a week or 2 later it can be beautiful. The early, vibrant red - orange - yellows typical of maples may be less, but the deep reds/browns of other hardwoods such as oak start to be more prominent and you'll see less green mixed in. The occasional execption year is when we get a big rain/wind storm mid Oct that will suddenly knock a lot of leave off the trees.

For us here in Saratoga Springs we have the luxury of doing half to full day trips for hiking just about any time we want with an endless choice of nearby trails, lakes, mountains to explore . October is perfect hiking season, especially if it's dry, so we'll typically pick a good-weather day and just enjoy the time outside. Walking a trail, kicking through the crunchy fallen leaves, finding a cider mill (for the donuts) on the way home) is all part of the overall fall experience. We're not "sit in the car" types. Some years we'll book a later October weekend getaway further north in NY, near Lake Placid if the weather is good.. Colors may be waning, but cool crisp air, thinner crowds, and nice hiking trails make for a perfect weekend.

rachellynn99 May 17th, 2020 06:58 AM

We always go to New England between about October 12-20. That is my Fall Break at school so my husband and I go then. We have flown into Boston, Portland and Burlington. I think my favorite area was around Mt. Washington in New Hampshire. In fact one year the colors were so vibrant that I literally cried at the beauty. It was breathtaking.

In Maine we enjoy Portland Lobster Company for a great lobster roll by the water, and walking and shopping around downtown Portland. We normally have our anniversary dinner ( which we also celebrate during this time at the restaurant Five Fifty Five in Portland. We also enjoy driving up to Acadia National Park, which is wonderful, although it's a super long day from Portland. We like Freeport as well and Booth Bay Harbor has a cute B and B- Top Hat Inn we have stayed at that is nice. We did a Lobster Boat tour in Portland and a foodie tour in Boothbay as well as Bar Harbor. We also like to hang out around Kennebunkport looking at the shops and eateries and the beach.

In Massachusetts, I like driving around the campus of UMass, and we went to South Deerfield to the Yankee Candle Store- which is honestly a treat. I also love Emily Dickinson and have made the trek down to Amherst a few times to visit her museum and home.

In Vermont, I would recommend staying in Middlebury at the Waybury Inn. It's a wonderful Bed and Breakfast and a good jumping off point for exploring Vermont. We spent one whole day driving around to covered bridges and cute little farms- I just found by looking at Vermont tourism stops and enjoyed the scenery and little towns very much. Woodstock and Burlington are both great.

In New Hampshire the Mt. Washinton Auto Road is terrific and the Kancamangus Highway is also just breathtaking. We've driven both multiple times. In North Conway, NH there is a cute little place to eat called Peaches that we normally eat at.

I hope you have a wonderful time. We won't be going this year as my job has restricted out of state travel for employees with talks of mandatory self quarantine if we do travel out of state, and I just can't do that at the moment so we'll see. I hope to be back at it in 2021.

jeverett May 17th, 2020 10:57 PM

Thank you all for the incredibly helpful suggestions. These have gone a long way in helping us plan.

We initially considered flying into Boston because we have JetBlue points that would have paid for our round trip airfare from Portland, Oregon. However, seeing that JetBlue is suspending service until 09/30 between Portland and Boston, booking on JetBlue and thinking our flights won't be cancelled in October is wishful thinking at best.

We will likely fly into Hartford via Delta and fly back from either Hartford or Providence, and splurging for refundable tickets seems like it's worth it this time around. We will likely hold off on booking flights until there's a bit more certainty, but we will book our hotels and car rental to make sure those are secure.

Based on the comments and suggestions, it looks like Brattleboro is ideal and I'm even more confident in our itinerary. Just trying to figure out where to base ourselves after we leave Vermont. Was thinking perhaps New Haven or Mystic for a couple of nights before moving on to Rhode Island.

I do like the idea of basing in Middlebury, as suggested by Rachellynn99 if my wife can arrange it so that we're able to extend our trip and fly in Oct 6th instead of the 9th. If that was the case, we would fly into Burlington and spend a few days in northern VT before heading to Brattleboro.

As it stands now, I think there's a 50/50 chance we go on this trip, and spending the extra money refundable flights seems to be the reality of planning ahead right now during uncertain times. Thank you all again for your help.

oldemalloy May 18th, 2020 06:09 AM

For flights, do also checkSouthwest, they fly into both Hartford and Providence and you can change without a charge as long as it is for the same cost flight.

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