It’ll still be scenic in the fall. Conway to Wolfeboro is only about 45 minutes. A couple of hours drive along the lake shore and back up to Conway to catch the Kanc over to Lincoln seems doable. I wouldn’t spend the night, but if there’s some flexibility with time I think it’s worth it.
I’d honestly prefer 302 from Conway, through Crawford Notch, and back down 3 to Lincoln. The Kanc can be a very crowded tourist road (no one goes there, it’s too busy) that makes you have to pay more attention to the cars in front of you than the scenery. Plus it seems like every time I’ve driven that road in the past 5 years it’s been raining or foggy (except for last October, Franconia to Portland, which was admittedly a very nice drive).
Route 302 has what I feel are far superior views - the Willey Range, Webster Cliffs, and views of two sides of the Presidential Range are all stunning. Then you get Franconia Notch on the way south (Cannon Cliffs and Franconia Ridge). Plenty of places to pull over for views, some nice short and well-worth-it hikes (Arethusa Falls, Mt Willard, Cannon tramway, Cloudland Falls on the Falling Waters trail, Flume Gorge, the Basin, all 2 hour hikes or less), and lots of local eateries if you’re in need.
I also agree with @elfkin477, the drive across Maine to NH is long and arduous. The maps don’t do it justice. Bar Harbor isn’t close to anything, and the roads are not great - lots of turns and intersections, no good scenery, nothing to stop for, just driving through small town after small town stuck behind slow drivers on two lane roads.
I appreciate and will look into every suggestion.
What about driving down Route 1, more or less along the coast?
Picturesque?
mmm
I drive rite route 302 all the time, so maybe I’m just inured. Yeah, it’s a pretty drive. And yeah, look for hiking opportunities along whatever route you pick. Lots of really nice short hikes available in that area.
At various times, from Portsmouth New Hampshire I’ve been on Route 1 up to Portland, Maine, and down to Massachusetts to the Amesbury area, and picturesque didn’t come to mind.
There are a couple of tiny parks with revolutionary cannons and stacks of welded together cannonballs, but that’s about the only thing I noticed that looks different from every other average New England town.
I liked Mount Ascutney with it’s hang-glider platform. If you’re short of time or energy you can drive about 3/4 of the way up by car.
A few times, Rte 1 from Brunswick up to Rockland and/or Bar Harbor (and back) for me, and it isn’t any different than the Portsmouth to Portland stretch.
Oh, look, a cement factory. Woohoo.
I’d skip Freeport all together, instead go from Bar Harbor to North Conway, take the Kancamagus over to Lincoln, and head into VT from there.
Burlington VT is a nice place, you can also drive up through the northern island of Lake Champlain (Grand Isle up to Alburgh) before heading into Canada.
North Conway has a lot of outlet stores and is probably more attractive and more walkable than Freeport. (Although i haven’t personally been to Freeport, maybe its nicer than the impression I’ve gotten from friends’ visits.)
@fachverwirrt is right on about breweries in the Waterbury area. I will say that The Alchemist can be very shoulder-to-shoulder. Maybe in the fall it’s more chill, but when I’ve stopped by in the summer it’s had a busy summer festival vibe.
I’d pick Lawson’s (Waitsfield) over Alchemist (Stowe), but your friends might be more impressed about a story that you went to the Alchemist, which still seems to hold a place of reverence in the beer community across the country.
Also in Stowe is von Trapp brewery. Not quite as notable, but if you’re into some basic but good versions of German beer styles, that can be a good spot to stop.
And, it does look like you’ll be continuing on through Burlington… and there are a zillion breweries here in town. I usually point folks to:
Zero Gravity and Queen City breweries. They are across from the street from each other, and are probably represent the best local beer in Burlington. Queen City is maybe not winning any awards, but their variety in styles make them worth a visit.
We’ve also got Vermont Pub and Brewery - great place for lunch, and good beer (some recipes are better than others). It was opened by Greg Noonan, one of the early “pioneers” of the modern craft brewing industry. He passed away relatively young around 2010, but his role in the Vermont and US beer scene can’t be understated.
I agree with the recommendation of others to skip Freeport. It’s not terrible, and I do prefer it to Conway, but it’s certainly not anything I’d put on a “must see” list. I’ll also second (or third) the preference for Quebec over Montreal, but they’re both quite nice. If I may offer some driving thoughts as someone who grew up in VT, currently lives in ME, and has put in some miles crossing northern New England between the two…
Cross into NH from QC at Hereford/Canaan. Rte 3 will take you to 26, which runs past the Balsams Resort (hopefully it will re-open some day, in the meanwhile, it’s quite picturesque) and through Grafton Notch, which has a variety of hiking options. Route 2 will take you to I95 in Newport, passing through Skowhegan, which is the Empire Falls of Russo’s book, and home to a nice sandwich spot, the Brick House Kitchen. Then through Bangor (home of Bagel Central and, from a literary standpoint, Steven King’s gothic house, an excellent public library, and a good little used book store: Pro Libris) to Acadia.
Acadia is great. Cadillac has wonderful views on a clear day, and the carriage trails are beautiful. Atlantic Brewing is OK, but not great. Likewise Mason’s in Bangor.
Exit Acadia by way of Route 1 south to Belfast, which is a lovely little town and home to a pretty good brewery and restaurant in the form of Marshall Wharf. There are a lot of food options in town, including a great hot dog stand in the Reny’s shopping plaza. Fort Knox and the Penobscot Observatory are worth a stop on your way to Belfast, as is the Maritime Museum in Searsport.
Then it’s Rte 3 to Augusta. Lake St. George brewery isn’t worth a stop, but John’s Ice Cream definitely is. Pick up I95 in Augusta for a bit, and then head to 302 through Conway and Crawford Notch, where the AMC has quite a few hiking options. Consider dodging Conway by way of Hurricane Mountain Rd from Fryeburg, ME, which should still be open, and also has some nice hiking options.
I would strongly consider a night at the Mount Washington Hotel. It’s gorgeous (and has a heated pool), and puts you in a good position to take the cog railway. Then continue on 302 through Bethlehem, where I need you to stop at RekLis Brewing, as I have yet to try it and would love a report - it always has a busy patio during the warmer months. I can vouch for Schilling Beer Co in nearby Littleton, which specializes in lagers and also makes very good pizza. Bishop’s Ice Cream is also well worth a stop in Littleton.
Get back on the interstate in Littleton (93 to 91 North) to get to St Johnsbury, VT, where the Fairbanks Museum and Planetarium is pretty incredible - it’s a Victorian curio cabinet writ large, and a great example of a big fish doing well by his small town (there’s also a stuffed moose). There’s a decent sandwich stop just down the block, but get back in the car and take Rte 2 into Danville, where Three Ponds makes great sandwiches and pours local beers right on the town green. Stay on 2 for the scenic drive to Montpelier and Waterbury.
On review, I see I missed your intent to go to Lincoln, NH. I assume for Franconia Notch, which is nice. All of the Presidential Range is pretty.
Wow, lots of good stuff here. I have some work to do, good thing I have several months before the trip.
I wonder if you know me. My one rule on vacation, which I announce regularly, is “ice cream every day”.
mmm
The Vermont Teddy Bear Factory in Shelburne, VT gives a very entertaining tour.
Lost River Gorge in New Hampshire is also nice, possibly nicer than the Flume Gorge, with some cool features on the hiking trail. (If you’re skinny enough, you can make it through the “lemon squeezer” - I’ve never been able to.)
In Montreal, I’d recommend the Biodome and the Insectarium.
I saw a moose crossing the road in front of me as I pulled out of the parking lot of the Lost River Gorge. Only one I’ve ever seen outside of Alaska.
I can get behind that. Listing the Ben & Jerry’s factory on your itinerary did make me suspect that you would be interested to hear of other options. Sadly, a lot of the road-side stands close over the Labor Day weekend.
If you ride the Cog RR or drive the Auto Road up Mt Washington then I probably wouldn’t bother with the aerial tram at Cannon. If you’re intent on going to Franconia Notch to hike the Flume Gorge (it’s really a walk, not a hike) take some side trips to the Basin, Mt Pemigewasset, or Artist’s Bluff. BTW, reservation are needed for Flume Gorge. For ice cream in the area I would go for Udderly Delicious or Coneheads. For beer, The Woodstock Inn and Brewery is a good choice. And as previously mentioned, Schilling up in Littleton has a great following.
An interesting dining option in the areas is the Cafe Lafayette Dinner Train, a 5 course meal served on a 2 hour train ride south of the Notch. Another old timey attraction is Clark’s Trained Bears which is well suited for kids but IMHO an outdated concept.
That train ride looks really nice, I may consider that.
I will definitely pass, however, on the trained bears. 
mmm
A third or fourth vote for Quebec City! I’ve been to Old Montreal many times and Quebec City 3 or 4 times. Quebec City is far more scenic and memorable, and not far off your route. They have good ice cream places too.
And another vote to skip Freeport and try a small town like Belfast or Bucksport instead.
I’m going to 4th or 5th skipping Freeport. Unless you REALLY like shopping and crowds, there are so many better stops in Maine–Deer Isle, Belfast, the whole peninsula south of Rockland, hell, even Portland–it’s become very foody.
However with regards to Lost River gorge, the website says that it opens in May and closes in mid-October, with limited hours in October. I only know this because I wanted to see it myself during the eclipse but I won’t be able to yet this year unless I come back in summer.
With regards to the viewpoint from the belvedere atop Mont Royal, I would recommend it if you like unified skylines. I myself do appreciate them, as opposed to skylines where each individual building pops out from all the others. Montreal has the second-best looking unified skyline to me behind Chicago.
In general, the old buildings don’t contrast horribly with the new buildings because the old buildings seem to be so much smaller that they seem a different medium entirely. (As opposed to why Chicago is good, which is because there aren’t a lot of extremely new glassy monstrosities contrasting with the old Art Deco and mid-century International buildings.) (And of course “old” is relative in both locations, since the “new” buildings in Montreal are almost as old as the “old” buildings in Chicago.)