Oh, late August. How you tease–tickling us with your glorious summer rays, knowing full well that the cold harsh hand of winter is waiting just out of distance, ready to slap. While we could lament the end of this care-free time in Maine, let’s consider something: at this moment, summer is basically that super hot, way-out-of-your-league chick you somehow tricked into dating you. And yes, much like that slumming beauty, this season is going to leave the heck out of you real goddamn soon. But not today, my friend. You’ve got a solid three, four, hell, maybe even five weeks out of this seemingly impossible relationship. So take advantage of the time you’ve got left together. Because let’s face it: you’ve got a long, cold, lonely winter ahead of you filled with nothing but memories and empty bottles of lotion. Unless of course you have a ski house, in which case, you probably get laid all year long.
So now that you’ve dealt with your impending breakup with summer, how do you get your cookies while you still have time? Well wouldn’t you know it, inspired by my vacation last week, I’ve got some suggestions for end-of-the-summer activities in Maine.
1. Get yourself to a Maine island, stat!
Whether you’re near Penobscot Bay or Casco Bay, you need to hurry your buns down to a ferry terminal and get on a boat. Bring a bike, pack a lunch, probably grab some beers, and invite someone good looking to spend the day with on an island in Maine. Why someone good looking? Have you guys ever seen LOST? They’re stuck on an island and there’s pretty much only one unattractive person (sorry, Hurley); as a result, everyone is constantly getting down with each other. If somehow you get marooned on this island, you’ll be thanking me for the advice. Anyway, since I’m a Portlander, I like to catch the ferry out to Peak’s when the island mood strikes. It’s just $7.70 roundtrip, and it’s only 15 minutes on the ferry before you find yourself in island paradise. Jump off the pier, get a drink at the Inn on Peak’s Island, and scoot down to the beach for some late August R&R. While these islands are beautiful all year long, those ferry rides are slightly less fun in January weather so I suggest taking advantage now.
Tip: If you want to get rowdy, head out to Peak’s on a Sunday afternoon for Reggae Sunday at Jones Landing.
Casco Bay Lines ferry schedule here
Penobscot Bay ferry schedule here
2. Go Upta Camp!
If you live in Maine, you either have a camp, or fifty of your closest friends have one. Whichever the case, get in the cah and drive upta. For people not from Maine, a “camp” is what snobby out-of-staters might call a “cottage” or a “summer house.” It’s not a cottage. And it’s certainly not a summer house. This isn’t the Hamptons. This is Maine, son. And in Maine, we pack 25 people into a two bedroom wooden camp and call it vacation. It rules. The blankets are roughly 23-years-old and seldom laundered. None of the silverware matches. And there is a lake very close by–preferably just a few feet away. Last week, I took my first vacation in a dog’s age and invited everyone I know to my family camp in Belgrade. We swam. We drank. We ate lobster (except my one unfortunate friend with a shellfish allergy–Sorry Josh). We jumped on a water trampoline. And we played a lot of card games with an incomplete deck of cards. Follow suit.
3. Skinny Dip
This is most likely the best and most tanned your body is going to look all year so take your clothes off and get in the water, damn it. Be a complete turd and shout YOLO if you want. Actually, no, don’t say that. But do get in there. There are so many lakes and beaches in Maine for baring it all, though perhaps, not legally. But I’ll turn a blind eye (as in I won’t call the cops; my eyes will definitely be open because I’ll be peeping for sure if clothes are off). Seriously though, there’s nothing more liberating than swimming in the nude. Most of my skinny dipping escapades occur late night so as not to upset the disapproving eyes of unfun people. Another tip: do it with friends. You’ll get a good giggle the next day when you realize you all saw each other naked. It’ll bring you closer. Trust me.
4. Strut Your Stuff on a Portland West End to East End Crawl
Not that you can’t do this the rest of the year, but I prefer the walk in the summertime when the weather is fine. If you’re old enough and responsible enough to partake in some adult beverages, I suggest making this walk into a sort of pub crawl expedition. Portland ranks among the top U.S. cities in restaurants and bars per capita, so a West-to-East (or vice versa) crawl will definitely keep you busy and might make saying sayonara to summer that much easier. Also, you can feel better about those beer calories because, hell, you’re walking!
5. Lead a Tourist Astray: “You Can’t Get Theyah From Heyah”
Just because.

Drop some knowledge.