Brooksville’s Oakland House stays in the family with new owners

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The Oakland House and Cottages is reopening for its 129th season owned by a new generation of the Littlefield family. ©Hilary Nangle
New owners of the Oakland House, the ninth generation of the Littlefield family on this original king’s grant, plan to reopen the restaurant as well as rent the cottages. ©Hilary Nangle

Rick and Robin Littlefield, cousins of the late Jim Littlefield, have acquired Oakland House Inn and Cottages from Jim’s wife, Sally. Rick and Robin are the ninth generation of Littlefields to operate this property, a king’s grant to the family back in 1765 (see my 2008 story). This year, 2018, marks the 129th season the Littlefield family has welcomed guests to the property.

Rick and Robin also own Robin Hood, the international summer camp across the road. They plan to operate the old hotel, eight cottages (Sally kept two as rental properties, Lone Pine & Crows Nest), and the Hostel@Acorn and to reopen the restaurant.

Here’s an excerpt from their welcome letter:

Our intention, in this first summer, is to continue to welcome guests in the seaside cottages. We have started renovations on the inn’s restaurant, which has been shuttered for the past several years, and expect to open by the end of June. The Oakland House is its own entity and will be separate from our other business, Robin Hood Camp. However, because we do specialize in fun and adventure, we will offer guests more opportunities for outdoor activities, such as powerboat excursions, kayaking and sailing, hiking and horseback riding, to name a few.

Oakland House oozes classic Maine. The comfy, rustic cottages salt the woods and shoreline edging Eggemoggin Reach.

Check into one of the comfy cottages at the Oakland House. ©Hilary Nangle
The Oakland House cottages are decorated in a comfy rustic Maine style. ©Hilary Nangle