What's the best time of year for this trip?
How many days/nights should we allow?
Any recommendations for shuttle services?
Best time of year? I have no idea, we have done two family trips there, late July into August, and early to mid August. I have no complaints even though that is likely peak paddler season. There was enough water to rumble over the riffle beside Big Island, the bugs were between not bad and not present, the weather was unfrigid enough to swim and the days long enough in camp twilight.
That was perfect for a kids out of school family trip. September, after the grade school and college kids are back in class, may be better, if cooler.
How many days? If you launched at Lobster Trip, went up into Lobster Lake for a night, then down the W. Branch to Chesuncook and took out at Ripogenus that would be around 50 river/lake miles. You could easily do it all in 3 or 4 days if Chesuncook was calm, but I would take at least a week and layover at some of the nicer sites, especially sites near the west end of Chesuncook that allow for day paddling explores from camp.
We used Allagash Gateway for vehicle shuttle, with them driving our vehicle back to Ripogenus. Not sure if they still do that, but it was convenient, our van was waiting in their secure area at the take out and we did not have to load and unload a shuttle trailer on launch day.
http://www.allagashgatewaycamps.com/services
I may be preaching to the choir, but in either guise, back shuttle with your vehicle or trailer shuttle with your boats and gear, have your crap organized and ready to go. Folks still packing their gear when it is time to load the trailer do no one any favors.
On the other hand folks who can not figure out what goes where in the canoe at the launch point have done us many favors. See ya and thanks, we will be miles downriver before you sort it out. Hope you find a site before dark.
Other stuff in the previous discussion. Bring a big tarp, the rough hewn ridge poles are very long and very tall, and extend out to the fire pit.
Get the tarp up early. Summer can be thunder stormy. And windy. I temporarily tied one end of a giant blue poly tarp to the seat of the picnic table while I wrestled it over that tall ridge pole to stake the far side. When I stepped down off the picnic table a gust caught that tarp like a billowed mainsail and upended the picnic table. I was laying atop the table
Ride em Cowboy holding it down until the gusts calmed.
Yeah, it gets windy. Choose your Chesuncook transit carefully. I would want to come out onto the lake with at least a days
insurance time, just in case. And make any mid lake crossing early in the AM.
Given a week to cover the distance I would be hesitant to pass up a delightful campsite in early afternoon. It never felt like campsite races, but we were content to make 8 or 10 miles a day, with a leisurely morning pack up, and an early to make camp
Oh this is a nice spot afternoon.
YMMV. I would not camp at anything less than a B minus site if the day was early and a batch of maybe better sites just a few miles away.