Gina2003

A few of us want to plan a trip to Maine in Sept 2021 (after Labor Day). We were thinking of renting a house in Southwest Harbor. We've never been to that area. We like easy-med(ish) hikes, food, the coast, boats/water. Is 4 days enough for that area? Southwest Harbor good base? Then where? Somewhere north of portland.(love coastline up thru falmouth so looking for something new).. Monhegan Island? We will have a car. We like to walk to dinner (and happy hour). Honestly, open to any and all ideas as we plan local travel.
Like many on this forum...I miss travel and appreciate the feedback and tips! Thanks. Be Well.

dfrostnh

Monhegan is a full day with a long boat ride but nice hiking. You would want to pack a picnic lunch to enjoy on the trail sitting on some rocks looking out to the ocean.
I let the Acadia experts answer questions about that area since we usually spend time mid-coast. Can you add time for travel since it's a long way by car to that area.
In 2019 we rented an ocean front cottage near Rockland. We chose that area for proximity to our favorite lobster places but the cottage was out on a point, dirt road, etc. Kind of remote. I don't think we had wifi so that might be a condiseration for you when you choose a place to rent. But keep in mind lobster shack places can go on reduced hours after Labor Day. Check if you have a place in mind. Oddly enough after many visits to Maine we headed up later than usual to the Rockland area and there was hardly any line at Reds Eats in Wiscasset so we stopped for the first time. Definitely one of the best lobster rolls in Maine but usually it's a long long wait to get one.
Brunswick might satisfy your restaurant/happy hour requirement. It is inland but you can do some good hiking in the Harpswell area. Download the guide to conservation areas. Not as rugged as Acadia however. I am a big fan of the Brunswick Farmers Market that meets on the common on Fridays.

A shorter boat ride but no hiking involved would be a lighthouse tour with the Maritime Museum in Bath. Bath is just north of Brunswick so it would be an easy activity to do. Check to see what is offered after Labor Day.
I have hopes that our next trip to Maine would be to visit some of the places on the cheese trail. You can find some wineries such as the one in Rockland and can visit several in one day. There are tons of breweries in Maine. Unfortunately we rarely drink alcohol anymore but you might investigate whether there are any distilleries. There's one in Tamworth NH that is amazing to visit with a fun tasting. There must be some in Maine.

ldatt22

I went to pemaquid point many years ago. Drove from NY. It was nice. I went in the summer. The water was cold at the beach. It was also rainy. Just stopped at various motels.