On The Island...
Our two ‘famous’ restaurants are Cook’s Lobster & Ale House (great beer selection & patio) and Morse’s Cribstone Grille (best house salad dressing).
Bailey Island General Store (BIGS) has a good selection for groceries, beer, wine, liquor, and kitchen for some freshly cooked items (pizza, etc).
Land’s End Gifts is our go to spot for our favorite Maine trinkets gifts for visitors including bobblehead Moose and lobster magnets. Some nice views on the south side too!
Island Candy Co, which is on Orr’s Island but still close, has great homemade chocolates, candy, and ice cream. They close late so we always visit after dinner.
Harpswell Heritage Land Trust has a lot of great hiking trails, like the Giant Steps on the island.
Bath is where Bath Iron Works are, you can see the Navy ships being made including the Zumwalt class. Nice downtown area with great shops and a new brewery the river walk is also nice. Fort Popham and Old Popham beach are worth the drive south to, maybe 20 minutes south of Bath.
Wiscasset is home of Red’s Eats, which probably have some of the best lobster rolls (cash only!). Not a large downtown, mostly art galleries, but if you’re hungry- stop here, it’s worth the wait in line.
Boothbay Harbor has a quaint downtown, lots of shops, and a neat ‘little’ aquarium to see baby lobsters. The botanical gardens are a nice visit if the weather is accommodating.
Rockland has a mile long breakwater lighthouse which is a neat but can be technical walk, it may not be ideal for older or younger visitors. Rockland has a nice little downtown, and a ferry to North Haven and Vinylhaven islands.
Camden has a mountain you can drive up for great views, a nice downtown area, and a beautiful harbor. A great place to stop for lunch.
Harpswell Neck has a Dolphin Seafood & Marina, great food % blueberry muffins. Behind the town offices is the cliff walk and fairy houses. The wine selection at Black Sheep and Beer Shop can’t be beat, the owner has some good stories… and books. Watch for signs since its small but the collection is impressive. Mitchell Field is home to the summer concert series which is nice to relax at.
Brunswick has a great downtown, lots of shops and restaurants, a great farmers market, the Androscoggin Swinging Bridge, Flight Deck Brewing Co., and a great way to spend a rainy afternoon. Check out Wild Oats for epic breakfast sandwiches if you’re early enough (great prepared foods if you’re not though)! Also check out Libby’s for our favorite lobster rolls. Gurnet Landing on the way to Brunswick also has good lobster rolls. There is a Shaw’s & Hannaford’s for most groceries, Shaw’s has red snappers too.
Freeport is home to a lot of outlets, a great state park for hiking, and the Maine Beer Co.
Portland is an hour south. The waterfront area is kind of touristy/commercialized, but still worth the walk around. Our favorite place to eat is Highroller Lobster Co. But plenty of other awesome places like Eventide Oysters, Central Provisions, Duckfat, Becky’s Diner, etc. There are some great breweries Bissell Brothers, Shipyard, and Allagash. If you have young kids they have a great children’s museum.
The Saco Heath Preserve is a neat little hike and flat the entire way (and tons of blueberries in season), it’s near Scarborough which has a couple small breweries/restaurants in its old mill buildings.
Kennebunkport/Kennbunk has a scenic downtown, some good restaurants, and a neat transportation museum.
Portsmouth, NH is a quaint little town with a lot of good restaurants/bars/shops along the harbor called the river walk. They also have the NH state liquor store which has excellent prices.