If you're planning on staying in Portland at all and the weather cooperates Peaks Island is nice. We had our kids and took a short ferry over. We rented a golf cart for an hour and drove around the island, explored a little of the shore and then ate lunch at a restaurant that has patio seating. We were there in the summer but we had fun. We got ice cream and walked the town a little. It wasn't all day or anything but neat to check out.
There is also the Damariscotta Pumpkinfest & Regatta the weekend of 10/7-10/9 between Portland and Acadia. Not sure what events would be on the 7th.
I have never been personally so it may not be great but it is on my bucket list to do one day. It looks like a cute town and festival. Check it out and see if its something youre interested in.
Acadia is also on my bucket list. Again, I haven't been (yet) but people love it and I'm sure there's lots to do that way. We might go up there this fall.
I was in Acadia in July and it was magical, so beautiful! Bar Harbor is an adorable town and will probably be nice and quiet after the summer rush but a lot of smaller places may be closed as it's after the season. Some close on September 1 and others wait until Columbus Day, so maybe check websites before you head to certain restaurants/activities.
That will probably be THE peak leaf week, or close to it, so go inland at least one afternoon. If you stop in Camden, the drive up to the top of Mt. Battie is nice. There are a bunch of short hikes in the Camden/Rockport area that will get you to beautiful, sweeping vistas of the ocean and hills of fall foliage. Rockland is also one of my favorite towns in Maine, with two great art museums, cute shops, and an easy ferry to Vinalhaven or a more ambitious trip to Monhegan Island if you want to take a day to explore one of Maine’s most iconic islands.
Another stop I absolutely love, but tourists hardly visit, is the Eggemoggin Reach area on the way to Acadia. Stonington is the prettiest working harbor in Maine, and Flye Point in Brooklin has a completely unknown but cool little island you can walk to at low tide.
Other great spots you might want to visit between Portland and Acadia: the Coastal Maine Botanical Gardens in Boothbay has these cool, 20-foot-high trolls made out of wood, and just in general beautiful walking trails. I also love the Driftwood Inn at the end of Bailey Island, just so relaxing and beautiful.
Of course go to Acadia! I think 2-3 days is about right. You might want to check the cruise boat schedule for Bar Harbor and avoid going on those days. To me, the trails at Sand Beach and the top of Mt. Cadillac are musts.
Portland is all about restaurants; my personal favorites are Minato, Terlingua, and Cong Tu Bot on Washington Street, Honeypaw, Duckfat, and Eventide on Middle, and Central Provisions in the Old Port. But there are so many more. Allagash Brewery is a good tour. The East End park is incredibly beautiful. The whale watching boat is a great afternoon, or just a ferry ride around to the islands, but wear warm layers if you go out on the water in October, even if the weather is nice on land. I also always take visiting friends to the Portland Head Light, Two Lights State Park, and Higgins Beach. They’re all along Route 77 about 15-30 minutes outside of town. Feel free to PM if you have specific questions. Have fun!
That will probably be THE peak leaf week, or close to it, so go inland at least one afternoon. If you stop in Camden, the drive up to the top of Mt. Battie is nice. There are a bunch of short hikes in the Camden/Rockport area that will get you to beautiful, sweeping vistas of the ocean and hills of fall foliage. Rockland is also one of my favorite towns in Maine, with two great art museums, cute shops, and an easy ferry to Vinalhaven or a more ambitious trip to Monhegan Island if you want to take a day to explore one of Maine’s most iconic islands.
Another stop I absolutely love, but tourists hardly visit, is the Eggemoggin Reach area on the way to Acadia. Stonington is the prettiest working harbor in Maine, and Flye Point in Brooklin has a completely unknown but cool little island you can walk to at low tide.
Other great spots you might want to visit between Portland and Acadia: the Coastal Maine Botanical Gardens in Boothbay has these cool, 20-foot-high trolls made out of wood, and just in general beautiful walking trails. I also love the Driftwood Inn at the end of Bailey Island, just so relaxing and beautiful.
Of course go to Acadia! I think 2-3 days is about right. You might want to check the cruise boat schedule for Bar Harbor and avoid going on those days. To me, the trails at Sand Beach and the top of Mt. Cadillac are musts.
Portland is all about restaurants; my personal favorites are Minato, Terlingua, and Cong Tu Bot on Washington Street, Honeypaw, Duckfat, and Eventide on Middle, and Central Provisions in the Old Port. But there are so many more. Allagash Brewery is a good tour. The East End park is incredibly beautiful. The whale watching boat is a great afternoon, or just a ferry ride around to the islands, but wear warm layers if you go out on the water in October, even if the weather is nice on land. I also always take visiting friends to the Portland Head Light, Two Lights State Park, and Higgins Beach. They’re all along Route 77 about 15-30 minutes outside of town. Feel free to PM if you have specific questions. Have fun!
I went to Portland earlier this week (only 4 days, sadly) and omg Terlingua was so amazing. It was basically just a trip to eat and drink beer (plus some kayaking and biking around Portland and Peak's Island) and it was all so delicious.