This Redditor can't be the only one planning to propose to his girlfriend in Portland this summer. Whether you're visiting from away or you're a born-and-bred Mainer, this town would make an excellent setting for a wedding proposal. Some popular locations suggested by Maine redditors included Portland Headlight, Eastern Prom, and Sumner Park on Munjoy Hill, along with all the picturesque islands in Casco Bay.

While these are all fine and dandy, might I suggest that they're a little predictable? Sure, there are plenty of romance-lovin' ladies out there who love a good ask on the knee at sunset, but I'd argue that Portland offers some weirdly perfect spots to propose to the girl who marches to the beat of her own drum.


1) Recreate the Magic of An Old-Timey Train Scene

If you pay a visit to Portland's Narrow Gauge Train Museum and book a waterfront tour on their itty bitty trains, you could mimic the classic romance of a "come baaaack!" scene in an old war movie, jogging along the bike path next to the train and catching up to propose once it stops (tour guides may not be thrilled at the prospect of you jumping the train en route). If you go on one of their designated ice cream tour dates, you could even celebrate the occasion with a little free dessert.


2) Love Among The Taxidermy

If we learned anything from Kendall on this season of The Bachelor, it's that taxidermy is now an approved kind of weird. This comes in handy with our Cryptozoology Museum at Thompson's Point, filled with disturbing evidence and creations of mythical oddities. For extra points, work in a line like "I don't know if I believe in Bigfoot, but I believe in us." Eh? Ehhh?


3) Becky's Diner at 4am

A self-proclaimed Portland Institution having been featured in multiple national spotlights and an episode of Diners, Drive-Ins and Dives, Becky's is toted as Portland's best breakfast spot time and time again. Make it there before first light when the doors open and the pungent, bearded fishermen flood the counter. Order blueberry pancakes and a lobster omelet, then pull out your little black box and kneel on the freshly mopped hardwood floors. Ask your girl to eat breakfast with you every day for the rest of your lives. Then slam food in your face and go nap it off. What better way is there to start a Maine engagement?


4) Love Note on the Mailboat

I have yet to venture out on the ferry that delivers mail to Casco Bay islanders, but I hear it's a hell of a ride. Craft a love note for your fiancé-to-be to start off the journey on theme, and for extra cheesiness go down on one knee upon arrival at Little Diamond (or Great Diamond if you've been saving up for that rock for a while). As long as she's not seasick, she's sure to say yes!


5) Fiancé City

Convince that SO of yours that you've got a hankerin' for onion rings that only the Bridgton Food City deli can provide, then make her day by kneeling next to the parking lot sign with a different kind of ring. Nothing's more romantic than a parking lot for the start of a real Maine love story. Plus, judging by the history of amusing reader boards Food City has provided (see below), I'm willing to bet it's cheaper than an arm and a leg to get your proposal posted larger than life.

Contributed by Food City
Contributed by Food City

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