Tiffanyjones331

In the early stages of planning a trip to upper New England next (2022) fall (likely the Last week of September) 5 days likely M-F
Flying from Cleveland but likely will fly into a cheaper airport (like Boston) and rent a car. Need/want to see Vermont, New Hampshire and Maine we want to visit Boothbay Harbor in honor of a dear friend who loved it there and recently passed away.
We definitely want to see as much foilage as is possible.
It will be our 15th anniversary so romance and memories are important.
we like (easy)hiking, bird watching, sea food (for her), the beach (and swimming though we know that may take place at a hotel vs the ocean given the timing) and gardens. We have previously gone whale watching but would love another similarly memorable activity.
And itinerary or must sees or advice welcome and appreciated

suze

Those three states covers an awful lot of territory for only 5 days' time. Hartford CT is another airport you can consider that is handy to southern VT and NH. Though Boston would work better for coastal Maine.

Welcome to the Fodor's US forum. Others should be along soon to chime in with some ideas. I used to live in VT and NH but the road trips I did were spontaneous, I'm not much help other than to say it is a beautiful time of year and a wonderful part of the country to visit. Wishing you the best! Enjoy!!

tomfuller

Consider taking the Amtrak Lake Shore Limited out of Cleveland (#449) at about 5:50AM on a Sunday morning. You arrive in Springfield MA about 12 hours later (5:30PM). Spend Sunday night in a Springfield motel and rent your car on Monday morning in Springfield MA which should be a bit cheaper than renting in Boston. The one way coach fare is less than $50pp currently.

dfrostnh

The last week in September is a little early esp for the coast where it is warmer. Best color that early would be in NH White Mountains. Also consider flying into Manchester NH which at one time was a good deal.

From Boston, head up I93 north to NH and then take I89 N to Vermont. I liked the Norwich Inn which is just across the state line into Vermont. Norwich is also home to King Arthur Flour which has a great store but you might like lunch at Simon Pierce in Quechee (see if there is glass blowing demonstrations) and everyone else will suggest visiting Woodstock VT. King Arthur has baking classes and if you are interested sign up way in advance. They sell out. Head next toward Meredith NH and check schedule of nature cruises on Squam Lake in Holderness (Squam Lakes Science Center). The one we took was early September around 3pm and we saw a lot of loons and eagles. The boat is a large pontoon boat and you will want to bring binnoculars. From Meredith you can go north on I93 thru the western side of the White Mountains. The Flume is a popular hike for tourists and the visitors center is very interesting. When you head to Maine take the Kancamagus Hwy thru the mountains then let google maps tell you shortest route to Boothbay.
Boothbay's Maine Coastal Gardens are wonderful and would require some easy hiking. Check out the Bath Maritime Museum's lighthouse cruises to see if they run mid-week. If not, you can always take the Mailboat tour of Casco Bay from the Old Port Area f Portland Maine. Might not be great birdwatching but there's some narration as it makes stops at various islands. If you take the first cruise in the morning your companions will be workers headed to jobs on the islands and you'll be back in the Old Port in time for lunch. A romantic cruise might be their evening one to see the lights come on. Do a google search of best lobter rolls to get a list of possibilities. Google's quickest route from Meredith to Boothbay is 3 hours but it will take you longer if you go further north to take the Kancamagus. I actually prefer the google route since it goes thru Tamworth. If you like alcohol spirits, the Tamworth Distillery is beautiful, fascinating and offers tastings.

I'm not sure you can do my suggestions in 5 days. From Boothbay you can get on I95 south to Boston, Your last chance for a romantic dinner might be in Portsmouth NH in one of the restaurants that look out on the harbor.

J62

It looks like there are nonstop flights from Cleveland to Boston on Delta, JetBlue and AA, but no nonstops to Manchester or Portland. Given the limited time you have a 2hr non-stop flights makes the most sense.
The end of Sept is a bit cold for swimming (hey, July and August are too in Maine...). Cap'n Fish has boat tours out of BBH. Puffins, seals, whale watching and they are highly regarded. An alternative would be a schooner harbor cruise on the Eastwind. It's not a wildlife tour but a beautiful sail through the harbor/bay.

Macross

Check about which toll responders work as Masseschusets booths are unmanned. We put our GPS on toolless roads. I would ask for the newer building in Norwich Inn. My bathroom tilted so badly and had food poisoning from that last lobster roll in Maine. Not a great combo. You can also see Andrew Pearce woodworking store in the area. I have seen Stephen Pearce pottery in Ireland. Very talented family. Woodstock is beautiful but my brother said they just spent 250 for the smallest room ever. The Norwich was a little over 200 a night. Vermont is my favourite. Our beach in Maine was very rocky but we still enjoyed the night. We flew into Bangor. The coast is beautiful. We have flown into Boston and then rented a car from there as well as Hartford a couple of times. I am in the Adirondacks now and we started in Maine on Tuesday. Because I was so sick we didn't go to King Arthur, bummer on that. I didn't even get to sit in a rocker on the front porch of the Norwich. The restaurant offerings were slim to none btw. I know it is due to COVID. My husband got a salad to go. I think Woodstock has much more to offer. The lakes in NH were beautiful. I am always looking for those downtowns with charm.

HappyTrvlr

As mentioned above, your dates are too early for fall leaf colors.
Columbus Day Weekend is often when you find the best colors but they change in the north first dependent on cooler temperatures.

J62

The toll roads in MA, NH and ME all have a "pay later" option so transponder isn't mandatory, nor is avoiding toll roads. You need to call in within 7 days with your license plate #.

dfrostnh

I should add that north of Manchester NH I93 starts getting scenic and eventually goes thru White Mountains. I89 to Vermont is also a pleasant drive. There are some state highways that parallel the interstates which give you an option is you can do slower and wish to drive thru some towns.

Macross, sorry you were sick and didn't enjoy Norwich. I've stayed in both old and new parts of the Inn and prefer the old but probably the most fun was both times were a mini Fodors meet and greet to take a baking class at King Arthur. Looks like the restaurant across the street, Carpenter and Main, is on reduced hours and menu. Vermont has had stricter rules than every other state so the OP should check before the visit. A lot of NH restaurants have had to reduce hours because they don't have enough help. Lobster shacks in Maine may be weekends only after Labor Day when kids/help go back to school. There are plenty of sit down restaurants but for lobsters we like the uninsulated cook shack with picnic tables by the water.