Greene County Success Stories

Captain’s Inn Point Lookout: A Five-State View

Captain’s Inn Point Lookout in East Windham has re-opened, as the landmark once visited by FDR has been refreshed and is ready to exceed the dreams of 21st Century travelers.

The Inn, located on Route 23 at a spot 1900 feet above sea level featuring a five-state view, revealed their progress on the renovation during their soft opening this summer. Its new owner, retired U.S. Merchant Marine Capt. Wayne Hamilton, and new chef, Wayne’s son Jason Hamilton, are excited to welcome new visitors, as well as guests from Point Lookout’s long history looking to create new memories.

Hamilton found the Inn while shopping for a pool hall location, an activity he was very fond of after retiring from the military in 2000. After passing by the property, he eventually bought it, moving here to become a first-time restaurant and hotel owner.

He then completely re-did the kitchen and renovated the building, once known as the Inn at Point Lookout Mountain Inn and Victorian Rose Restaurant.

After its renovation, Captain’s Inn Point Lookout has a dining room, bar, event space, and several decks overlooking the amazing five-state view, with common areas that encourage guest interaction and support the Inn’s tagline of “come for the view, stay for the company.” From the inside of the restaurant and the decks, you can see the White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshire Mountains of Massachusetts, the Helderberg Mountains of New York and the Connecticut Valley. The 13 lodging rooms above the restaurant have also been renovated, and all are non-smoking.

Featured entrees on an eclectic menu include Skirt Steak, Chicken Florentine, Shrimp Scampi, and a variety of classic and contemporary appetizers. “We have our father-son relationship, but when the doors open, he’s just Chef Jay,” Wayne Hamilton said. “He’s actually completely over-qualified.” The most popular items to date have been the Mac ‘n’ Cheese kid’s special, Seared Salmon, Lamb Shank with white bean casserole and a calamari with Thai sauce special.

Hamilton also plans on taking advantage of the view that draws diners in by adding an ice cream stand to takeout customers, a traditional feature of the historic Point Lookout. “Soon, people can just stop by and enjoy the view and eat some ice cream,” he said.

The inn and restaurant also serve as a venue for private parties and weddings, featuring Cliffside arbor and a formal perennial garden that serve as a beautiful backdrop for that special day.

Find Captain’s Inn Point Lookout at 7604 Route 23 in East Windham. It serves dinner Thursday through Monday from 5 to 10 p.m. Reservations are recommended, especially for window seats: 518-750-8436.

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Visit the Captain’s Inn Point Lookout website.

Adapted from a story published August 26, 2015, at

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Topics: Success Stories