In August 2021 all 15 of us in my extended family went to Bar Harbor, Maine for 7 days/nights. We stayed the entire time at Bar Harbor Inn (https://barharborinn.com/) which was beautiful and full of charm. I would recommend this hotel because 1) gorgeous views abound of the harbor! 2) we had a nice balcony to sit out and enjoy it 3) there is a walking path that goes by the front of the hotel to enjoy the views in a different way 4) there is a really good free breakfast 5) wonderful outdoor pool 6) the hotel is historical with beautiful flowers and walking paths 7) nice restaurants 8) Walking distance (5 mins) to town. There is not good parking in town, so walking is preferable. Our favorite restaurant was the Terrace Grille, which was outside, and had great views of the harbor. The problem was that everybody else likes the view at this restaurant too so the wait to get a table can be long. The hotel gives you a "cut in line" pass for the restaurant but it only worked against people not from the hotel and it didn't save us much time. Also, if the weather is bad they will close up quickly. The only con about this hotel was for our large group it was hard for us to find a place to hang out together to play cards and games. For this reason, I would consider renting an Air BnB house on the water. There were several beautiful ones but I'm sure they are booked up quickly! And one last thing to consider, we were able to rent out a big private dining area at the hotel for my parents 61st wedding anniversary with a lobster dinner. That was amazing. There was a balcony off the dining room overlooking the harbor (same one that's been there over 100 years) and we had a photographer come take family pictures since we are not all together too often. Another very nice hotel to consider in town is the Harborside Hotel. https://www.theharborsidehotel.com/
Getting to Bar Harbor: we drove from Chicago and stayed one night in Syracuse NY. Two days was plenty of time to get there. One the way back we took 3 days because we wanted to explore all the cute towns on the coast of Maine (Camden, Kennebunkport) and Newburyport MA. We enjoy driving and exploring and so this worked well for us. On the way back we stayed in Brattleboro, VT and then Jamestown, NY. We saw Lucille Ball's home and met up with Chicago friends at Chautauqua Lake. If you want to fly you'll probably have to go through Boston and take a tiny plane to the Bar Harbor airport (which is what my sister's family did and warning, it can be tricky to get an uber or taxi from this airport), or you could rent a car and drive up from Boston. Or fly in to Portland, Maine which is a bit of a drive from Bar Harbor (but less than Boston).
Some activities to do while in Bar Harbor:
Of course see Acadia National Park. There are many hikes, you can ride bikes, get up early to see the sunrise over Cadillac Mountain (get your reservation in advance- I think they are doing this a few months out due to covid). Do not try to ride your bike from Bar Harbor Inn to Acadia like we did. First, you'll get lost without navigation, it's up hill, it's farther then you think, you might get killed from the cars that are zooming up and down the hills. Just bring your bikes in on your car. We brought our bikes from Chicago and you can also rent them there but then you have to have a bike rack on your car.
Of course go whale watching! barharborwhales.com
Rock climbing! This was 100% worth it and amazing. I never thought I would do this but I loved it and they will tailor it to your abilities. Beautiful views! Adrenaline rush! Amazing! My niece had so much fun she wanted to go again a different day but they were all booked up. If your hips are not flexible you might struggle but it's still worth it for the views. I am afraid of heights but I was able to do this (I almost threw up looking at the pictures online but once I was there I was fine). https://www.climbacadia.com/
Sea Kayaking! www.acadiakayak.com This was a fun way to see birds, seals, and porpoises up close in the area away from the tourist crowd.
Fishing: we rented a boat just for our family (I think there was a limit of 6 people per boat). This was another scenic way to see the coast of Maine whether you like fishing or not. We stopped and talked to the lobster catchers (I am sure they have a more professional name) and it was fun to learn about lobster trapping.
At low tide there is a sand bar you can walk on over to a little island.
This really worked out well for a big family group trip to do these activities together. It is a special place where you might want to go every summer.
Restaurants: Eat lots of Lobster rolls! I really liked the ones with corn our first night at Geddy's. Other favorite restaurants: The aforementioned Terrace Grill overlooking the water, Thrive for lunch (casual, healthy!), Side Street Cafe for mac n cheese, Route 66 had good basics for the kids and no wait, Jeannie's Great Maine Breakfast and Jordan's Restaurant for breakfast, and Project Social for Tapas (the kids didn't like it though). Blaze had the best pizza. I really liked the Jordan Pond ice cream but Ben & Bill's was good too and also MDI ice cream is famous but very long lines and unusual flavors.
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