I want to emphasize…Moody’s Diner has great PIE. Not great meals. Just saying.
Are the flights into Manchester a LOT cheaper? If not…you would save yourself a LOT of unnecessary driving by flying into Portland ME.
There’s absolutely no reason to go to Freeport unless you want to shop at the outlets and/or Bean’s. (Bean’s also has an outlet, BTW, in addition to several separate buildings.) If you are camping types, the camping department is almost irresistible. It’s hard to leave without some cool new gadget. 
IMHO, outlets are outlets everywhere, but Bean’s is different.
Brunswick is a very pretty town, and Gelato Fiasco is wonderful. If you like dark coffees, be sure to have a cup of God of Thunder. There are plenty of good lunch spots in Brunswick, but if you really want a lobster roll, there is a little convenience store with a couple of tables that is widely acknowledged to be the best: Libby’s Market on Jordan Street. They will make it with melted butter or with mayo, grilled roll or not: your choice. Personally, I recommend grilled roll and melted butter.
I am not a fan of Ogunquit. It’s very touristy. I think it’s a shame to skip Portland in favor of that.
Thumper- yeah, it was a huge difference- 383 round trip for two from NH, over a thousand round trip for two from Portland.
Grilled with buttah is exactly the way I like those lobster rolls too, Consolation!
Well, I am either going to be happy with my decision to choose Ogunquit over Portland, or I’m going to want to kick myself. I will be sure to let you know! This is the hardest part of planning!
Two musts if you’re up in that part of Maine (writing this right now from the south coast of Maine on vacation): Red’s Eats for a lobster roll in Wiscasset and a visit to Pemaquid Point. Enjoy!
Agree with Consolation. Wouldn’t skip Portland for Ogunquit.
I will graciously disagree with @Consolation about Freeport.
If you have never been to the LLBean flagship store, it’s worth at least a visit. As noted, there is also a LLBean outlet in Freeport where returns and the like are sold.
Unless you are BIG shoppers, I wouldn’t allocate a lot of time to Freeport, but really…I also wouldn’t skip it if you haven’t been there. It’s on the way for you as you drive north…or south.
Also, it’s a long drive from Manchester up to Camden and back down to Ogunquit. It will eat up a lot of time on a short trip. You may want to consider staying in one place and then daytripping out from there. (Although your itinerary does sound like fun). Have been coming here the past 11 years with the fam, so happy to help.
I have yet to go to Red’s, but beware: the lines are as legendary as the lobster rolls 
If you do insist, LOL, on going to Ogunquit, there is an interesting art museum there, the Museum of American Art. Not in the same class as the Portland Museum of art–ahem!–but worth a visit. There is also the Ogunquit Playhouse:
http://www.ogunquitplayhouse.org/
You can visit Portland on your next trip.
I agree about LLB’s camping store (sheesh, I get a rush just going to my local REI.) But every time I’ve been to Freeport, it’s congested and parking is tough (even off season.) But there is a Northface outlet. Everyone says stop in Freeport but it’s little different than any big outlet venue in New England. Decide if it’s a pilgrimage, to you.
But, for a lobster roll, if you mean that leg, my vote is drive 10 minutes south to Harraseeket Lunch. Not the inn, this is a shack on an inlet. That’s a reason to go to (South) Freeport.
Once you’re in Brunswick, going north , taking Rt 1 is one of the reasons to see coastal Maine. Traffic should be ok, except in Wiscasset, depending on time of day.
If you go to Owls Head, have lunch at the Owls Head General Store, a local icon. Look it up. Then before leaving the area, you can drive a tiny bit south to Holiday Beach. It’s a private residential area, you’d just drive in/out, but the view from the road is why we love Mid-Coast.
Agree about Ogunqiit. Seems you’ll use it as a base, but don’t miss Portland. See the other thread for dining ideas. The Portland Museum of Art is a treasure. Thing about it and the Farnsworth is they’re small, easy, delightful.
Second Thumper’s view–except for LLBean, Freeport isn’t that interesting (it’s full of outlet stores). If you’ve never been to LLBean, it’s worth stopping there and then continuing on your journey.
Well, I really like Wolf Neck Woods in Freeport. It’s a state park. A short walk through the woods takes you to a beautiful shoreline, and you can see an osprey nest in an island very close to the shore. It’s one of my favorite places to go for a walk.
Agree about Portland. It’s great and would be a nice place to stop, even if you could only fit it in for a few hours on your way to Ogunquit. Have fun!
295 is a highway. It looks like every other highway in the country.
Take route 1. Sure…there might be some traffic. But there is so much along the way you will miss by being on 295.
Totally agree with lookingforward that Haraseeket Lunch is definitely the place to go for lobster in Freeport, as I said on that other thread. (Actually it is in South Freeport, a pleasant little village on the water.) Now that this is NOT the Harraseeket Inn on the main drag in Freeport.
But you can only do so much. If your goal is to get to Camden from Manchester on the first day while being able to enjoy the scenery and not drop from exhaustion, I’d drive straight to Brunswick and have lunch at Libby’s and Gelato Fiasco, then drive on to Camden. At most, I’d stop at Bean’s. I don’t think you want to try to cram every single thing in and be exhausted.
Oh, and at Bowdoin there is the polar museum, which is unique and well worth a visit, it’s small, so it doesn’t take long:
http://www.bowdoin.edu/arctic-museum/
And they have an excellent small art museum that always has interesting special exhibitions:
http://www.bowdoin.edu/art-museum/index.shtml
Both are free. At least, I’ve never paid to get in.
BTW, both MaineLonghorn and I live about equidistant between Portland and Brunswick.
It’s a good place to live! The NAMI course I’m teaching in the fall will be in Brunswick.
We have never regretted moving to Maine 31 years ago, even though we could have had better-paying, more prestigious careers elsewhere. The quality of life is amazing. 
I second @Consolation. Drive straight up to Brunswick for lunch/ice cream and then to Camden. I love playing tourist in Maine, after living here for 18 years. You’re going to have a good time no matter what - enjoy!
Ha, I like to think the lines at Red’s are part of the experience. At least that’s what I told myself.
I recommend using yelp and/or tripadvisor photos for assessing the lobster roll recommendations mentioned here and on the other ME thread. As a lobster roll connoisseur and frequent consumer, I can basically look at a photo of a lobster roll and get an idea if I will like it or not. I don’t want tons of mayo, no celery or other stuff, not even lettuce. Just lobster, the more the better, the bigger the pieces the better, very light mayo or butter, on a buttered and grilled New England style top split hot dog roll. That’s the way to do a lobster roll.
We happen to be friends with the owners of Ken’s Place in Scarborough. Their lobster roll has been rated as one of the top ten in Maine. This weekend, they’re throwing a big party at their house. The food will be out of this world! They do a HUGE lobster back - big fire in the back yard with more lobsters than we will be able to eat. I can’t wait!
I think they’re all “rated as one of the top ten,” Lol.
We stopped at Red’s once, not at peak, and the line was estimated at 90 minutes. That’s a chunk of time we never wanted to devote when there are so many choices. It might be different if one is saying in Wiscasset or can play tag team with buddies.
Agree to drive straight to Brunswick. (Looks like 2 hours.) But then Rt1 to Camden. The coast is special.
I want to move to Maine. These threads make me ache a bit.