Maine Treasures: Oakland House & Shore Oaks

Previously, I blogged about the Rusticator Restaurant here. Now let me tell you about the resort itself. The property has been in Jim Littlefield’s family for eight generations. A king’s grant to his ancestors in 1765, it sprawls over 50 acres edging Eggemoggin Reach, in Brooksville. It’s a magical setting, the type often portrayed in post cards; the kind that fuels dreams and spurs memories.

Oakland House refers to the resort and its 15 rustic cottages; Shore Oaks is the Arts & Crafts-style, shorefront B&B, which is where we stayed. Families favor the cottages, and many return year after year, generation upon generation. Any why not? It’s the kind of place where you can reconnect, because you’re disconnected from phone, TV, even Wifi. Instead, swim, sail, paddle, play lawn games, chase fireflies, hike, build fairy houses in the gardens or simply chill. Rates include daily breakfast and dinner in the Rusticator, or if you’re here on Thursday night, the shorefront lobster bake is a tradition.

Shore Oaks, built in 1907, is quieter, secluded at the edge of the property, with a wrap-around porch on the water’s edge and a dock complete with gazebo stretching out into the blue. Look to the left, and there’s that soaring pray-as-you-go bridge to Deer Isle; to the right, Pumpkin Island and its lighthouse backed by the Camden Hills. In front, windjammers often sail by.

Inside, it’s decorated in period style, with an emphasis on comfort; it’s not at all stuffy. Gab with other guests in front of the fire or play a game of cards. Guest rooms, for the most part, are spacious, some large enough to qualify as suites, two have wood-burning fireplaces. Most have private baths, but these tend toward old fashioned, and some are tiny. Breakfast is included; add dinner for an additional $30 per day.

No, Oakland House and Shore Oaks aren’t for everybody. If you must be electronically entertained, it’s not for you. But if you like to hike, boat and chill with family, you won’t find a better place.

UPDATE: Sad to report, Oakland House/Shore Oaks has closed.


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