COLLEEN WESTCOTT has dined all over the world, but she always comes home to Portsmouth — and on occasion, to Gilley’s iconic hot dog cart. “It’s been here 100 years, and it’s won Best Hot Dog contests, it’s been featured on travel shows,” the co-founder of the Portsmouth Eats tours said. “Their steak-and-cheese subs are amazing, and their poutine?” Westcott rolled her eyes at the mention of the diner’s take on the French-Canadian staple. “That very well may be the last meal I ever eat.”
Westcott and her son, Jonathan Carrigan, started Portsmouth Eats when he was 14 and looking for his first job. In the ensuing years Carrigan has never had a job flipping burgers or mowing lawns — but he and his mom have introduced thousands of people to a Portsmouth they never knew and what’s coming out of its kitchens.
As she strolled through Market Square, Westcott recalled that first summer. “We both loved food, we both loved travel,” she said. “I wanted him to know the history of the world, and food was the best teacher.”
They partnered in the first summer of Portsmouth Eats, a historical and food-sampling tour. The concept caught on, for both them and their guests.
Though they have since developed several tours with different emphases, the format remains the same: a walk around the city spotlighting history and tasting at least five different dishes. Their flagship product is the “Best of Portsmouth” tour, Westcott said. The restaurants partner with her to offer samples, such as the River House’s notable chowder, and the guests snack at the restaurant or, if the eatery is busy, in a nearby pocket park.
Several of her first culinary partners are still with her, Westcott noted, including the River House, Byrne and Carlson chocolatiers, and The Library. The Blue Mermaid was a huge supporter until they moved to Kittery, she said. She managed to enlist 10 dining spots that first year, and they were off.
Her most popular tour remains “Best of Portsmouth,” where foodies from out of the area recognize restaurants they may have seen on television. But it works for locals too, she added.
“One of the things that used to drive us crazy was that people came to Portsmouth and they were overwhelmed, so they ended up eating at the same restaurants, usually chains.
“I’m always thinking, ‘Oh, you were so close,’” Westcott said.
Westcott isn’t anti-chain, especially with limited local chains such as the Beach Plum and Me & Ollie’s. Rather, her emphasis is on uniqueness and creativity, whether it be served on cloth napkins with tablecloths or at Gilley’s formica counters.
The locals get the point, once they’ve taken the tour, and they come back and bring out-of-town guests, according to Westcott. She’s also done reunions, weddings and corporate outings.
Because the town is coming back from COVID, she’s scaled down her offerings for this summer. Tours will include Best of Portsmouth, Sweets and Treats, and the White Tablecloth tour, where featured restaurants are known for “exquisite” preparation and presentation.
History and insider tips
Sweets and Treats was the first tour Jonathan developed on his own, and is family-oriented, Westcott noted. It’s one hour, where her other tours are 2-1/2 hours. The samplings may include gelato, something from Ceres Bakery, a stop at La Mason de Mer for a macaron, or popovers with maple syrup at Popovers.
On “Best of Portsmouth” Westcott has free rein to explore the town’s history along with its menus. At The Library, she encourages guests to have their pictures taken with the gilded lions. “It’s sort of a, ‘Where were you?’ effect,” she said. She makes sure to point out that the building was owned first by Gov. John Langdon and then by brewer Frank Jones, and she points out the bas-relief (sculptured) faces of the two owners in the eaves.
She makes time for Portsmouth’s darker history, with a stop at the monument to the African-American Burial Ground, and is a walking expert on the shady history and epic renewal of Prescott Park. She points out places like the Friendly Toast, noting that it was featured on “Good Morning America,” and warns her guests to get there early if they don’t want to wait in line.
Insider tips and stories reel out of Westcott as she walks. She and her team, now Jonathan and two other guides, make sure to delineate between fact and apocryphal stories, and there are plenty of both.
She talks about the North Church, the tallest structure in Portsmouth, and advises guests that when they’re on their own and get lost, they should look for the steeple. “If you can’t find the steeple, you’re not in Portsmouth,” she said breezily.
Her attention to detail includes warning visitors when to step up or step down — and a souvenir, a bag of Port City Pretzels for each participant. “When they’re winding down at the end of the day, they’ll open the pretzels and talk about what a good time they had,” Westcott said.
What of the boy who needed a summer job? Jonathan is all grown up now. He graduated high school and the University of New Hampshire with a major in mechanical engineering — and eco-gastronomy.
“And,” his proud mother said, “he still leads tours.”