That late in October, you're going to be a bit late for the best fall foliage, but there's still some interesting scenery in that area.
I'd take a ride up Rt 26 through Grafton Notch State Park (interesting stop at Screw Auger Falls and some great hiking opportunities if you like to do that) to Errol, NH, then north on Rt 16 back into Maine and over to Oquossoc and Rangeley (nice lakeside community), and from Oquossoc south on Rt 17 (crossing the "Height of Land" -- highest point on the Maine state highway system with a great view of the lakes region -- and, as you get further down the road, a fairly decent chance of seeing a moose along the roadside)to Mexico/Rumford, then west on Rt 2 back to Sunday River. Entire loop is about 150 miles and should take 3 1/2 to 4 hours of driving time, not including any stops along the way. Not a lot of choices for lunch between Sunday River and Rangeley (and not a huge number there either)....lots of forest in the state park and privately owned woodlands....
Not sure how you're getting from Montreal to Sunday River, but if you haven't already been there, another good day trip loop is south from Bethel on Rt 26 to Norway, west on Rt 117 to Bridgton, west on US 302 to Conway/North Conway NH, north on Rt 16 through Pinkham Notch to Gorham, NH and west on Rt 2 back to Bethel. About 3 1/2 hours and 120 miles...
Along the way -- couple of nice Maine communities, great outlet shopping and a walkable, fun downtown in North Conway, the Appalachian Mountain Club headquarters complex (great stop for outdoors folks), possible great view of Mt Washington, passing thru a corner of the White Mountains National Forest, and some pretty Shelburne Birches on Rt 2 west of Gorham. Numerous good restaurant choices in North Conway for lunch....
Those are a couple that come immediately to mind -- am sure you'll hear from others as well...
You've gotten some good advice already.
I would add while on NH, to take Rte 302 to Bretton Woods and stop at the Mt. Washington Hotel. It's quite impressive and so are the views from the back of the hotel. Depending on the time (and money willing to spend - it can get costly for our family of five) that is also near the Cog Rail that goes to the top of Mt. Washington. (Not sure it would be in operation then?)
We love Portland, and the Old Port area has good restaurants and shopping. We also drive to South Portland to the lighthouses. Another 30 minutes south will place you in the Kennebunks. Along the way to Portland, you should look for "Paris Hill", a small historical village with a magnificent, incredible view of the White Mountains. (It is, I believe, a bit of a secret)
You might also wish to stop at the Shaker Village as you get closer to Gray.
Enjoy the trip
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