Bill Windsor samples a Ted's Bakery macadamia cream pie at the Yum Yum Tree at Ward Centre.

Discovering America,
one pie at a time

Isle desserts rank high in
a couple’s quest for the best
in the country

This is Bill Windsor's story, by the numbers: 148 days, 29,000 miles, 2,519 towns, 181 pies.

Three years ago, Windsor came up with the idea of journeying across America, visiting mostly small towns, collecting stories and eating pie. He talked his wife, Barbara, into the plan. "To our way of thinking," Windsor said, "small towns usually have a cafe where the locals eat, and they always have pie."

The trip began this year on April Fool's Day, when they left their home in Atlanta, Ga. It ended Aug. 26, after a flight back from Honolulu.

The result is a colorful Web site,, a journal of their journey, with stories about people, places and pies. Lots of pies, which were evaluated and ranked.

Windsor traveled the Honolulu leg alone, Barbara having family business to attend to. He spent five days wandering the island, asking everyone about their favorite pies. He tasted six, plus a number of cakes and Leonard's Bakery malassadas, which he dubbed the best doughnuts of the trip.

Ted's Bakery's Chocolate Haupia Pie topped his isle tastings, scoring a 92, which put it in a tie for the No. 6 position overall. Also cracking the top ranks were the Hula Pie from Duke's Canoe Club and a fresh banana pie from Diamond Head Grill & Market, both scoring 90s.

"The goal originally was just relax, travel on two-lane roads, meet people. ... We wanted to see if there's a kinder and gentler America. And there is," Windsor said.

They had planned to focus on many aspects of small-town life, but the pie angle was what drew attention. "People very quickly made the pie the most important thing. ... Eventually we called the trip 'The Pie Trip.'"

Windsor describes himself as a "serial entrepreneur," having run 44 businesses in 33 years, most involving publishing. But he also owned a restaurant for a couple years, where he developed the scoring technique used on the pie tour.

He auditioned hundreds of potential dessert items for the restaurant menu. "I tasted a strikingly similar number to the number of pies we've eaten on this trip," he said.

The official point scale went from 1 to 100, although no pie ranked lower than a 45. "It's sort of the A, B, C, D and F."

This giant robot in Hobe Sound, Fla., led the Windsors to the best key lime pie of their trip.

THEIR PIE TASTING was by no means all-inclusive. They basically asked the locals for recommendations and tasted everything they could, sometimes passing through several towns in a day. Windsor has the sort of warm, upfront personality that easily draws stories out of strangers. To coax out a pie suggestion would be a piece of cake, so to speak.

The first pie of the trip was a white chocolate coconut cream pie at the Shrimp Factory in Savannah, Ga. The clerk at the front desk of their hotel had recommended it. "She said, trust me, you gotta go there.'

It scored in the high 80s and remains in the top 20.

Many of their discoveries were made by chance: On Day 5, they were on the road in Hobe Sound, Fla., when a 40-foot robot caught their eye.

"We made a U-turn, which is the main thing we do."

The robot was the signpost for a restaurant and bar called Harry and the Natives, where they had the best key lime pie of the trip. In fact, for 92 days that pie was unchallenged at the top of the list overall.

The Windsors scored other desserts as well, from doughnuts to carrot cakes. One of their favorite items was a mango snow cone from Freddy's Fast Lube & Snow Cone Stand in Escobares, Texas.

They'd stopped to take a picture of the stand, a giant, rainbow-toned snow cone that apparently received electricity via an extension cord running to the fast-lube shop.

Windsor's encounter with the owner, Freddy Escobar, is recorded on his Web site: "Freddy asked if I wanted anything, and I said, 'I'd love a Coke.' He replied: 'Snow cone?' And I said, 'Sure, give me a snow cone!' He asked: 'Flavor?' I replied: 'Grape.' He said 'Mango!' I said, 'Sure, mango it is.'

"When I tell you my snow cone was AMAZING, please accept that I'm not exaggerating. ... The flavor was wonderful, but the consistency was what I couldn't believe ... like an ice drink with the consistency of frozen yogurt. I think Freddy should franchise; I can see Freddy's Fast Lube & Snow Cone Stands all across the U.S."

The No. 1 pie on the Windsors' list is a raspberry pie discovered on Day 100, in the town of Lyden, Wash., at a restaurant called Dutch Mothers.

"The raspberries were HUGE. Usually with a fruit pie you get the fruit in a water mixture that the fruit lies in. This was slightly congealed. This was really good."

At 97 points, the Dutch Mothers pie is at least 3 points better than any other pie on their list.

On Oahu, he was directed to Ted's by 20 different pie eaters. He paid an impromptu visit to the Sunset Beach bakery during a tour of the North Shore. Owner Ted Nakamura gave him a tour. Windsor sampled a number of Ted's pies and cakes, but he said the top-selling chocolate-haupia was by far the best.

"I don't like chocolate pies, but this one is different," he wrote on his Web site. "The chocolate is more like a candy bar than it is like a chocolate pudding. The chocolate was delicious, but the combination of the haupia (coconut) was just incredible."

Another recommendation sent him to Kelvin Ro at Diamond Head Market & Grill for the banana pie Ro used to serve at his Kahala Moon restaurant. Ro made one special for Windsor, who described it as "heavenly." He also liked the Diamondhead Torte (cookie crust with peanut butter, chocolate and bananas), which is on Ro's current menu, scoring it an 88.

The Hula Pie -- dessert after a lunch of fish tacos at Duke's -- is a monstrous creation of ice cream and macadamia nuts piled on a cookie crust, served with whipped cream and hot fudge sauce. "I cold have eaten it all, but I left half of it so I wouldn't be embarrassed."

An 11-year-old he met in an elevator sent him to Leonard's on his last day in Hawaii. "Since I started a doughnut franchise two years ago, I know doughnuts. These are without any question the best donuts that we've had on the trip, so I name them Best Donuts in America."

So, it's over. The Windsors are transcribing their tapes of the trip and are putting together a book, which probably will be out in a year. In the meantime, catalogs their adventures and details all the pies they tasted.

After 181 pies, cakes, smoothies and doughnuts, Bill is in recovery. "I gain weight just looking at food," he said. "I'm at least 20 pounds heavier than when I started the deal."

Prime pies

These are the top pies in America, as ranked by Bill and Barbara Windsor after their trip across the country. You'll notice that while most are truly pies, some are more general desserts.

1. Raspberry Pie, Dutch Mother's Restaurant, Lynden, Wash.

2. Key Lime Pie, Harry and the Natives, Hobe Sound, Fla.

3. Banana Heaven (bananas sautéed in butter, rum and brown sugar, served over banana bread), Blue Heaven, Key West, Fla.

4. Caramel Apple Raisin Pie, Plaza Restaurant, Santa Fe, N.M.

5. Apple Dumpling, Blues City Cafe, Memphis, Tenn.

6. (tie) Butterscotch Pie, Rogers Restaurant, Lexington, Ky.

6. (tie) Chocolate-Haupia Cream Pie, Ted's Bakery, Sunset Beach

8. Mango Snow Cone, Freddy's Fast Lube & Snow Cone Stand, Escobares, Texas

9. Rhubarb Pie, Dot's Diner, Bisbee, Ariz.

10. Olallieberry Pie (cross between a type of raspberry and a blackberry), Linn's Bakery & Eatery, San Luis Obispo, Calif.

Note: Two other Hawaii pies, Hula Pie from Duke's Canoe Club and Kelvin Ro's banana pie ranked just below the olallieberry.

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