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A valentine to life on Chase Creek: The first in a Reporter series on Shelter Island innkeepers

The story of the House on Chase Creek is a link between two pandemics — the Spanish flu of 1918 and COVID-19, which flared in 2020 and continues to haunt today’s world.

William Cummings, the owner of the B&B, has known Shelter Island all his life. Family members have summered on the Island for more than 100 years. His grandmother left Brooklyn with her young family when the deadly flu was raging and came to the Island with the hope it would prove to be safer. The same can be said for many families who left New York City when the COVID-19 pandemic changed lives in 2020 and people sought less congested places to call home.

During the first few months of the pandemic in March 2020, Mr. Cummings saw his business slack off completely. Everyone who had made reservations for the summer began canceling and he had no reservations through April, May and most of June. He considered renting the house to one person for the rest of the season.

But reservations began coming toward the end of the month. For July and August of 2020, he was close to being fully booked. People who had plans to stay at some large hotels that had closed for the season were happy to find a B&B able to accommodate them.

Those who came “became some of the most appreciative guests of the House on Chase Creek,” Mr. Cummings said. “The pandemic era has turned into some of my best years, financially and otherwise,” with many people discovering Shelter Island and leaving New York City to come to the Island.

“I love Shelter Island,” Mr. Cummings said. “Being on Chase Creek, I get to be in one of the best spots on this beautiful rock.”

Operating a B&B enables him to share with his guests “the magic” he sees on the Island. He tries to keep rates affordable so others can “experience the joy” he’s found.

The House on Chase Creek opened its doors as a B&B on Thanksgiving weekend in 1989, just two months after Mr. Cummings closed on the property. What prompted his decision was a desire to live around the corner from his father’s summer house.

He knew he couldn’t afford it on his earnings as a bartender at the Ram’s Head Inn. But by renting rooms, he could close the gap between his earnings and what it would take to buy the house.

He credits his former wife Sharon with being instrumental in getting the business started. “Without her help, I wouldn’t be where I am today,” he said. “The many people who helped with that first hectic renovation cannot be thanked enough,” Mr. Cummings said.

He continued bartending at the Ram’s Head during summers for more than 30 years while it was owned by Linda and James Eklund. “They were so hugely supportive in getting started with my B&B endeavor,” he said. “The business would not have existed without their help.”

But the beginning wasn’t all smooth. One of the first guests bounced a check and ruined some furniture.

“I wondered if it was always going to be like that,” he said. “Thankfully it has only gotten better.

“Shelter Island seems to attract the finest kind of people,” he said. “My guests constantly remind me of how lucky I am to live here. I enjoy sharing the guests’ joy.”

The Inn, like the Island, has changed with the times, with the addition of amenities such as WiFi and air conditioning, but the innkeeper tries to keep the spirit of Shelter Island’s past alive. He thinks even those who knew the Island in 1989 when he first opened the doors of the House on Chase Creek (and perhaps his grandmother who came to the Island in 1918) would recognize it today.

“If you’re trying to open a B&B here, you might also want a time machine to go back to the years when it was a bit more affordable,” he said.

If there’s a downside to operating a B&B, it’s the 24/7 nature of the job, Mr. Cummings said, noting that, “I’m always on call. Truthfully though, it usually doesn’t bother me because I’m doing something I enjoy.”

Occasionally there are problem guests but those have been “few and far between.”

For the past 10 years, he’s operated the House on Chase Creek on his own. With four guest rooms, he’s generally able to handle most tasks himself. But during the height of the season, he sometimes brings in housekeepers as needed. Despite the demands of the work, he finds time to serve as a volunteer with the Shelter Island Fire Department.

He books guests year-round but, of course, warm months are the times when he’s booked to capacity. It was a schedule he developed after college, bartending in warm weather and traveling around the world in winter months.

The quiet season also affords him time to make updates to the house without disturbing guests.

Mr. Cummings has a poem by Kurt Vonnegut, “Joe Heller,” he keeps on his refrigerator that helps him maintain his perspective and he recommends it to new home and business owners on the Island:

True story, Word of Honor:/ Joseph Heller, an important and funny writer/ now dead,/ and I were at a party given by a billionaire/ on Shelter Island. I said, “Joe, how does it make you feel/ to know that our host only yesterday/ may have made more money than your novel ‘Catch-22’ has earned in its entire history?”/ And Joe said, “I’ve got something he can never have.”/ And I said, “What on earth could that be, Joe?”/ And Joe said, “The knowledge that I’ve got enough.”/ Not bad! Rest in peace!