Hobnobbing With the Kennedys

by Nancy Bestor

windfall houseI’m a sucker for a Bed & Breakfast. When this type of lodging first became popular in the United States, I wanted to stay in a B&B on every trip I took. Even after Bob and I stayed in a kitschy one or two, where the proprietor wanted to talk and talk and talk to us while we drank our coffee first thing in the morning, I still found the idea of a B&B romantic. Maybe it’s because I’m nosy by nature and I can’t resist the opportunity to look around a complete stranger’s “home”. Thus, I was delighted to book a three-night stay in a B&B on Cape Cod for our family this summer. I loved saying those words, “Yes, I’m staying in a B&B on the Cape this summer,” in a voice not unlike Thurston Howell III’s wife Lovey might use.

The Windfall House, a colonial home built in the town of Sandwich in 1816, was exactly how I pictured it, complete with a thirteen-star, American colonial flag flying from the porch. Its location in Sandwich was perfect for exploring the Cape, although we quickly learned that Cape Cod boasts many sleepy towns with shop after shop filled with antiques. Since we’re not antique shoppers, we spent our time following my passion—food.


Fortunately, the restaurants I researched and determined we needed to try were spread out over several Cape towns, so we got to see many quaint spots in our quest for lobster rolls, fried clams and shrimp and homemade ice cream. We started each morning with a delicious home cooked breakfast, prepared especially for us each morning by one of the Windfall House’s delightful and friendly proprietors, Caleb Brown. Caleb and his partner Richard Waterhouse moved to Sandwich three years ago for Richard’s job as a museum curator, and when they bought the Windfall House, which had previously been a B&B, Caleb decided to continue running it as such. He does a marvelous job. Our rooms in the upstairs 100-year-old addition were comfortable, cozy and clean, and our delicious breakfast each morning featured frittatas, scrambled eggs, bacon, homemade muffins and breads, juices and coffee, fresh fruit and cereal, and more. And each evening, after exploring the Cape, we’d return to Windfall House, and enjoy a glass of wine or beer from the offerings Caleb set out every afternoon. Caleb was the perfect B&B host, knowing when to visit and offer information about himself and the area, and when to let a guest do their own thing.

Our favorite restaurant on the Cape, hands down, was the Seafood Shanty, a seafood shack with outdoor seating only, and scrumptious lobster rolls, well worth the seemingly steep price of $19 for a sandwich and fries. It’s hard to call a lobster roll a sandwich though, as the toasted and buttered bun is filled with chunky and moist bites of lobster with just a small amount of mayonnaise. On a side note, we also ate lobster rolls in Boston, at a wholesale lobster shack called James Hook and Co. The lobster rolls in Boston were even better than those on the Cape, perhaps because the lobster was so much fresher, having just moved from being alive in a plastic bin in the restaurant to dead and deliciously whipped with butter and mayo in my lobster roll.


The Windfall House is one hundreds (perhaps even thousands) of beautiful colonial homes on the Cape. It was fun (for me at least!) to drive past them slowly and get a good look. We enjoyed lazy days while there, sipping coffee in local shops, miniature golfing, browsing a weekend craft fair, seeing a movie at the local movie house, and stopping in the town’s local library.

Cape Cod may only be an hour’s drive from downtown Boston, but its sleepy and laid-back feel make it seem light years away from the big city.