The front room of Dick and Alice Thompson’s house on Thompsons Hill — with its sweeping view of the cove — is an excellent vantage point on what Southport is today, and what it was in years gone by.
The Thompsons have had a daily eyeful since 1964, when they bought the property from heirs of Dick’s grandparents. He’s the fifth generation to live in the house.
“I’ve been coming here all my life,” said Dick, 81.
In 1968, Thompson Cottages-Southport started with renting one of the four cottages, the one they call Dockside. It abuts Robinson’s Wharf and hangs out over the water, a perfect view of both recreation and occupation, the working lobster boats. Once a stable for sheep, Dockside is now a charming two-room unit.
Over time, three more cottages joined the mix: the tan, the white (a former gas station) and the gray. At present, the gray cottage is occupied year-round, but the other three remain open for business. After 50 years, that business is both brisk and familiar.
“Sixty-five percent of our visitors are repeats,” said Alice, 79. “Some of them have been coming for more than 20 years.”
In 1968, a week’s stay cost $125. That number has changed along with the years, although the Thompsons have kept the price stable relative to inflation while adding amenities. Cable TV and WiFi are among the features now, but the cottages retain the charm of a summer getaway.
Running the cottages was a family affair in the beginning. Alice and daughter Linda would handle the cleaning. Dick and Hugh were on upkeep duty. “Cars, homes and boats,” Dick said. “They all need maintenance.”
Nowadays, Linda comes in from her home in Bath on the weekends to do the books. Rachel Leeman has been with the Thompsons for 25 years, “putting our cottages in perfect order every Saturday of the season,” Alice said.
Initially, a stay at the cottages included boat rides to Spectacle Island and later on Burnt Island. Now, the perks are pieces of homemade pie cooked by Alice: lemon sponge, blueberry, chocolate cream or apple.
The Thompsons have adjusted their policies over time. Week-long stays are required, and parties are limited to two people. “We’ve had guests who invited half of Portland to stay with them,” Alice said. “But it’s been more of a plus than a minus. Our cottage guests are wonderful.”
The Thompsons have seen a lot. There have been two heart attacks at the cottages — “and two survivals,” Alice noted. Guests have become old friends. They have a plumber and an electrician at the ready, and along with Leeman and help from their kids, the enterprise hums along.
“We really don’t have to work that hard at it anymore,” Alice said. Still, the end of the season in October does bring a bit of a respite. “It’s kind of like being on vacation for us.”
A few years back, the Thompsons decided they would take things year by year as far as keeping the business going. So far, so good for 2019 and beyond.
“We’re here to stay,” Alice said.