Please help me plan an October trip. Landing in Boston, where we’ll stay a couple of days. Don’t need help with this since I know the area, but I’m looking for tips on drive to Maine & Maine itself. We have Camden, Acadia Natl’ Park and Freeport (where we’ll stay with friends for the weekend) penciled in, but would love tips on what to see/where to eat in these places and nearby.
Thanks in advance, CC!
I don’t know what it is like in October, but Ongonquit was pretty cool (hopefully I spelled it right!). Portland is kind of interesting these days (and if you get in that area, get down to south Portland and try Cap’n Newicks seafood, haven’t been there in a number of years, but worth going to if it is still as good).
Thanks musicprnt!
Definitely Portland, which has a great restaurant scene.
Another thought might be in rockland or camden, see if they still have day trips with the windjammer fleets there. A lot of their business is doing multi day trips,but some of them would do day trips, and it is pretty spectacular. Another trip idea, though it isn’t fancy, would be to drive up to Brunswick (where Bowdoin college is), and then drive out across a chain of Islands, to Bailey Island, it is a beautiful drive, very scenic, and Bailey Island is kind of charming, too.
On your way between Maine and Boston, stop by Portsmouth, NH.
I would also suggest adding the Boothbay Harbor area as a stop for a night or so. Visit the Boothbay Botanical Garden. Drive to and walk around Ocean Point.
Places to eat in Portland, ME (because you might need a little break from seafood): Duck Fat, Boda, Standard Baking Co.
Gelato Fiasco in Portland and Brunswick
Reid State Park (Mile and Half Mile Beaches) with a meal at Five Islands Lobster Co. in Georgetown, ME. - casual dockside seafood joint with stellar views.
Farnsworth Art Museum in Rockland, ME
I definitely recommend Ogunquit, love the walk on the Marginal Way, lots of restaurants and possibly Ogunquit Playhouse season still on. Kennebunkport also very charming plus you can catch a glimpse of Walker Point, the Bush family compound.
Totally enjoyed the botanical gardens when we had revisited Boothbay Harbor a few years ago. Wiscasset, Camden. all picturesque towns… of course there is Red’s Eats (think is the correct name) at the foot of the bridge in Wiscasset for lobster roll. Good lobster rolls in Ogunguit at the Lobster Shack in Perkins Cove.
Red’s Eats in Wiscasset for lobster rolls.
Great minds think alike!
Portland is the eating capital of NE. (There is a recent thread about this on the Boston Chowhound board.) It’s a very interesting place to wander around - Old Port, mostly but that area has expanded to the east. I could list restaurants all day: the overall quality is that high. If you want specifics, that’s easy. Fairly good art museum too.
Portsmouth, NH is also an interesting place. There’s the old town center on the water and Strawberry Banke, which is essentially an entire neighborhood along the water that’s been “preserved” in various ages, from colonial to 1940’s grocery store. That takes a while but if that interests you it’s worth the time. Portsmouth is across the river from Kittery, ME which is mostly outlets though I really like When Pigs Fly Restaurant - note: it’s the restaurant of a bakery chain started there - and my wife has a weird attraction to the DQ on the rotary.
In MA, the classic northshore towns to visit are Marblehead and Rockport and maybe Gloucester. Marblehead is almost sublimely pretty with streets lined with colonial and just after era houses - including one whose corner was cut away to accommodate Lafayette’s carriage when he returned as an old man. Rockport is two towns in one: Bearskin Neck juts out into the water and is lined with mostly silly stores selling kitsch and the like with cottages all around and the town center is so quintessential NE that it’s often used in movies (and has a bunch of art galleries). I admit to loving the streudel place out on Bearskin Neck and the view of the lobster shack has been painted about a gazillion times. Gloucester is interesting to visit, has an artist’s colony but is also not nearly as upscale. The drive around Cape Ann is really beautiful with the rocks and the shore.
Got to say I’m less a fan of Freeport: it’s like a stage set with some houses but behind are vast parking lots. It’s nice to visit the mothership LLBean at 3AM though.
Another favorite place is little Kennebunkport - where the Bush compound is (drive around the headland). Quaint, lobster rolls, etc. Though if you want lobster rolls, etc., there are a number of places out on rocks along the shore up and down the Maine coast. I’m not a fried food lover but they were “invented” at Woodman’s in Essex, MA, though the sort of consensus among people who eat a lot of that stuff is The Clam Box in Ipswich and Farnham’s in Essex are better. Ipswich is lovely. Essex, next door, is loaded with antique stores and isn’t so much a “town” as a spot with a lot of antique stores.
Because this region is so old, there’s a very long list of things to see. We’ve been members of Historic New England for years and still haven’t made a few old houses in Maine and NH.
YOU GUYS ARE THE BEST! Thanks so much.
Lots of good tips here–will add–Bailey’s Island is worth visiting; it is a postcard-pretty Maine spot. If you go there, stop in Brunswick on the way back and dine at Tau Yuan. The cuisine is Asian fusion and the chef is the daughter of a family friend. She was recently named a best new chef by Food and Wine magazine.
The botanical garden in Boothbay is called the Coastal Maine Botanical Garden. It makes all the top 10 gardens in US lists. It will blow you away!!!
Would Red’s Eats in Wiscasset still be open in October?? It’s an outdoor shack with picnic tables and a huge line of people waiting. It is delicious and worth the wait, but I’ve always been there in the summer. Google it to see when they close for the season.
If you go to Brunswick where Bowdoin college is (voted the best college food in the country), then go next door to Bath, where they have the Bath Iron Works & Maritime museum. Good for all ages.
I second Boothbay Harbor too. Just beautiful. And Portland is a foodie scene.
I agree about seeing the North area of Boston, as Lergnom suggested: The Rockport, Glouster & Cape Ann area is very typical New England.
Make sure you try Clam Chowda where ever you go! It’s fun to see how different & alike they can be in different parts of New England.
^^I just googled Red’s Eats. They close around Columbus Day weekend for the season. They also say that their menu dwindles the week or two beforehand to get ready for their close. So I think that may be a “no”. 
It really is good, but there are so many other seafood places up there that you won’t miss it!
@katliamom - Hopefully, you are going in the first half of October? If so, it will be prime leaf peeping time. Most businesses - lobster shacks and such - stay open until mid-October to catch the leaf peeper business. It does get pretty quiet after that.
If you eat in Bar Harbor, check out Mache Bistro, Cafe This Way, and/or Side Street Cafe.
I had my first lobster roll at Cafe This Way – it tasted like a light, buttery chicken salad. It did not taste one bit like fish or the sea. Sooooooo goooooood! The mac and cheese at Side Street Cafe is superb, and Mache Bistro is really good. They change the menu now and then but if you like steak, and it’s available, try their hanger steak, medium-rare – outstanding. (If it is not on the menu, ask them if there’s one in the fridge. That’s how I got mine.) I wanted to lick the plate, but my wife might have left me…
If you make it down to Southwest Harbor, try Beal’s Lobster Pier – best fish sandwich I’ve ever had. They catch the fish and clean them right there.
In terms of things to do on Mt. Desert Island, well, it’s beautiful everywhere you go – sights galore.
You can go inland and hike, or drive along the main loop and see the different coastal towns and features, or go up Cadillac Mountain to see views of the entire Island.
If you are up for a taxing hike, walk around the Tarn and then take the trail up the side of Dorr Mountain. The views just keep getting better the higher you go on Dorr.
If I got a lobster roll that tasted like a chicken salad sandwich, I’d ask for my money back. 
But it definitely shouldn’t taste fishy, either.
Haha, I would ask my money back too. I pay .88c for a pound for a whole chicken while I pay $6.99 for a pound for a tiny lobster. And it’s not even Maine lobster.
And lobster meat, shelled, will cost you at least $32/lb even in New England.