We go to Boothbay every year for Labor Day weekend. We stay on Southport Island (just off Boothbay) at Ship Ahoy Motel. It's a small family run motel - 3 buildings and 2 are on the water (bay) and very inexpensive. We've done this every year as long as I can remember - it started as the last weekend before school started and the last time to visit the grandparents in Maine for the summer (I think I've only not gone 4 years since I've been born and boy did I miss it). Now that I'm married with a child we have continued this tradition and include my in-laws. We always go to the Windsor Fair (same weekend in Windsor Maine), go to Pemaquid Point Light House and take a boat ride to "Cabbage Island" or a whale watch - not to mention alll the "lobster pounds" we visit.
uconndz-have you been out to Monhegan? I love going out there. Hometown fairs are the best.
Thanks for mentioning the hotel. Just checked the rates and they are the best. It sound silly but the bed in the guest room at my mother-in-laws is so bad I can't sleep there. We have only actually stayed there once which is a shame as she is right on the ocean. This motel is so reasonable that maybe it will be an option.
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