You Could Win an Inn on Swan’s Island, Maine, for Just $99 and an Original Essay

A lighthouse in Swan's Island, Maine.
A lighthouse in Swan's Island, Maine. / Timothy Krause via Flickr // CC BY 2.0
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For just $99 and a short, well-crafted essay, you could live out all your Gilmore Girls-inspired dreams and own a quaint New England inn.

The Harbor Watch Inn, located six miles off the coast of Maine on Swan’s Island, has two regular motel rooms with basic appliances, two rooms with full kitchens and balconies overlooking Burnt Coat Harbor, and a furnished one-bedroom apartment that the owner could either live in or rent out.

The island itself is pretty much the epitome of a sleepy New England town. It’s only accessible by ferry, 350 people live there all year, and the website specifies that “there are no McDonald’s, no strip malls, and no movie theaters.” There is, however, a lighthouse, a marine museum, hiking trails, and quiet, uncrowded beaches that might make you want to become the 351st permanent resident.

If owning your own piece of the tiny, water-locked paradise sounds like heaven, you can enter for a chance to win the Harbor Watch Inn here through March 31. In addition to answering a few questions about your experience, skills, and feelings about the small-town atmosphere, you’ll have to explain in 350 words or fewer why you believe you’ll succeed as an innkeeper and what you’d change about the inn.

For anyone willing to pen multiple essays and pay the $99 application fee several times over, go for it: According to a press release, there’s no limit to the number of applications one person can submit. They’ll all be evaluated by a panel of judges—led by retired school teachers—and the winner will be announced by mid-May. Not only will that winner get the property, they’ll also be awarded $25,000 to help them improve the inn and establish their business.

Contests like this one have gained popularity in recent years as a way to sell businesses to people who wouldn’t be able to afford them otherwise, but they don’t always go exactly according to plan—find out about the Humble Heart Farm, The Hardwick Gazette, and five other property prize stories here.