Day 1 – Monday

 

We’ll start off at the hotel, find 302, and head west. Portland and Windham aren’t all that exciting, but the scenery gets a little better as we get into and through Naples.

If you’ll be wanting something to wet your whistle later, Food City in Bridgton will be a good stop. They have a ridiculous beer selection, and they’re cool because they’re an employee-owned company.

Moving along, still on 302, we’ll bang a right in Fryberg. There’s a fun road you need to experience.

North Conway is full of places to eat in, so we’ll take a ride down the strip and let everyone get a good look. We can stop at a covered bridge or something at the other end and decide where we want to eat, bang a u-ey, and then stop somewhere to grab lunch.

Moving west, again, we’ll be on the famous Kanc (the Kancamagus highway). It’s a beautiful stretch of 112 with some fun corners. Careful on the switchback. Craig bottomed out once, but he was coming the other way (on the inside of the corner) and had a passenger.

We’ll find 302 again at the end, but this time we’ll be riding it east, and landing in Littleton for the night.

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Day 2 Tuesday

 

Well, we were on 16 a bit for Day 1 (over in Conway), but we’ll be on it a lot today. It’s a very pretty ride we only discovered a few years ago, and runs along a lot of the Androscoggin River. We’re actually going to also be in the neighborhood of the Connecticut River’s headwaters (up by the Canadian border in NH), but not close enough to visit. Instead, we’ll head up north and cross the ME/NH border in Rangely, then stop for lunch in town. The pickings here are a bit slimmer than Conway (confirmed just recently during the 2024 eclipse), but there are still good places to eat.

After lunch, we’ll saddle up and mosey east along 16 until we get to Dover Foxcroft (Dovah, as the locals say). Then we’ll bang a left, and head for Greenville to stop for the night at the foot of Maine’s biggest lake.

 

 

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Day 3 Wednesday

 

We’ll leave Moosehead Lake in Greenville, and head back toward Dover Foxcroft, then take a left and ride 16 a little while longer. This day can go a couple of different ways. In Milo, depending on who your guide is, you may get a harrowing story of a trip years ago in this neck of the woods. It involved crossing a stream on 2x8s, on an ATV trail,  in the middle of the woods, on a 700lb Vulcan 1500 Classic, just west of town. Before anyone asks… No, your tour guide will not be leading any tours down that same “road.” One trip was plenty.

If we take a right, we can stay on 16 and end the day early in Bangor. Some folks like old downtown areas, so this would be a good chance to see Bangor and Brewer (and a gigantic Paul Bunyan statue). We can grab lunch and dub around town. Bangor and Brewer are old, so there are a lot of historic places to see there (and Stephen King’s house, if that toots your horn).

Or we can take a left in Milo and make the road trip a bit longer. We’ll go up to Millinocket, then bang a right and start heading south again, skirting a part of The County (Aroostook) on our way back down. We’ll even teach you how to say I have been to The County in proper Mainah-speak (sounds like I bent The County) . We’ll grab lunch in Lincoln, then continue on through Orono and into Bangor. We’ll be staying in the downtown area, so even if we take the longer ride through Millinocket, people will still have time to venture around on foot. If Craig is your guide, he may leave you to your own devices. His wife’s employer has an office in town, and if she’s also up for the night he’ll probably go chill with her.

 

 

 

 

 

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Day 4 Thursday

 

We’ll set out from Bangor and take what locals call The Airline (Route 9) for a ways east. We’ll bang a right on 192, and head for Machias. Lunch will be there.

Afterward, we’ll be sticking to the coast as much as possible and make our way to Ellsworth. We should get there soon enough that we can take a little ride down to Bar Harbor (Bah Hah-bah, if you want to sound like a local). It’s a tourist town, so there will be plenty to do and places to eat. You may even see someone you know “from away.” We can explore Mount Desert Island a bit (and check off Acadia National Park if anyone’s got a bucket list of parks they’re working on).

 

 

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Day 5 Friday

 

This will be our last riding day together. I know, it sounds sad already…

We’ll leave Ellsworth and again try to hug the coast as much as we can. There will be traffic, but it will still be fun. Just pulling over near a crowded intersection (if the bikes are getting too hot), then shooting the breeze with folks walking by can be interesting.

We’ll stop in Rockland for lunch, and then make our way back to the hotel in Portland.

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Headed Out

What happens next depends on your travel arrangements. There may be a late flight out of PWM, or you can stay at the Sunday night hotel again and grab a shuttle to the airport Saturday.