Sandwich Recreation Department employee and gatekeeper Justin Harold clutched his clipboard and watched carefully as a steady stream of cars came and went from the beach parking lot next to the Drunken Seal Restaurant one afternoon this week.

His job is to be sure the new pay-to-park rules in that lot are enforced. He had a lot of educating to do as he approached beachgoers who were not aware of this season’s parking change, and Drunken Seal patrons who did not know they had to use one of the 17 designated parking spots closest to the restaurant, or park in the lot on the other side of the building.

The new rules comprise a pilot project, which adds paid parking at what is officially known as “Beach One” next to the Drunken Seal, and at a small lot at Ploughed Neck Road and North Shore Boulevard at East Sandwich Beach, which until now held the last free beach parking spots in town.

The town plans to add solar-powered kiosks, referred to as a meter, at Beach One and at the East Sandwich lot.

If the project is a success, these meters—where customers pay with cash or credit card and the automated teller prints a ticket that drivers display on their dashboards—will be installed at all of Sandwich’s beaches, which are currently served by beach attendants.

As beach season opened, delivery of the two meters had been delayed—a source of frustration to Sandwich Recreation Director Guy J. Boucher—so the gatekeeper is currently filling out a tag with the day’s date for those who pay to park.

As of the end of June, beachgoers at Beach One have these parking options: patrons with a Sandwich beach sticker can park for free; patrons without beach stickers can pay $20 to park for the day and pay the gatekeeper until the meter is installed; and for patrons looking for a quick, scenic stop or to put their feet in the sand for a few minutes or walk along the water, 11 free 20-minute parking spots and two free handicapped spots (currently monitored by the gatekeeper) are available closest to the beach in front of the concrete Jersey barriers.

The fourth option is to park free after hours—which starts at 4 PM.

“We are treating this like any other beach in town,” Mr. Boucher said regarding the Drunken Seal lot, whose conversion from free to paid has been a source of controversy between the town and Drunken Seal owner Christopher G. Wilson.

Although he said the first week of the new pay-to-park system had gone well, Mr. Boucher admitted that “change is hard.”

“Some people have misunderstood and they think you have to pay $20 extra, even with a beach sticker,” he said, citing an example.

Jordan Dolby and Jake Burnett, a young couple from Sturbridge, were on a day trip for their first visit to the Cape this week, and they pulled into the town lot next to the Drunken Seal.

“It said online that this was the closest beach,” Ms. Dolby said, “and that it cost $15 per day to park.” When the couple discovered that the fee to park for the day was $20, they decided to leave and go shopping instead.

Town officials have said that instituting an automated pay-to-park system at Sandwich beaches, for which this year’s pilot program is a forerunner, has been in the planning stages since 2013.

Mr. Wilson, however, has repeatedly made it clear that he takes the new pay-to-park system as a personal attack. He questions the timing of the pilot project, which—after decades of free parking—comes just after he bought the Drunken Seal property last year.

“The town chose to hurt a business that has been here for 30 years, that provides employment for college kids and other employees,” he said in a telephone interview this week. “The town chooses to make it difficult for me to run my business. They are directly firing a shot at me,” he said. “It’s so stressful.”

Mr. Wilson said he has received repeated phone calls in the last week from customers who want to know if they have to pay to park at his restaurant.

Although he assures callers that they can park free in the spots near the building or on the other side of the restaurant away from the town lot, he worries about the patrons who do not call and simply go to another restaurant instead.

Mr. Wilson said he is paying an extra $1,200 per week in employee costs because he has had to add a hostess out front and an employee in the parking lot on the other side of the building to be sure people parking there are coming to the restaurant and not parking to use the right-of-way to cut through to the beach, as the public is accustomed to doing.

He has looked into shuttling his 10 daytime employees to the restaurant from another parking lot in town. Many of the young adult employees are not Sandwich residents and are staying with relatives for the summer. They are not eligible for beach stickers, which Mr. Wilson would have paid for.

Mr. Wilson said he looked into getting insurance to have valet parking for the side lot, which is unpaved with no line markings, but it would have cost him thousands of dollars, “because they are kids” who would be doing the valet work.

He looked into buying the kind of shack the gatekeeper uses for the employee who has to be out in the elements in the unpaved lot, but the shack would cost up to $7,000 and the town told him he would need to go through the historic commission in order to put it on the property. “That’s a whole other permitting process.” Mr. Wilson said.

Of the restaurant business, Mr. Wilson said, “it’s really, really tough to make money. You only have four months. That’s all you have. It’s tough for everybody who runs a bar.”

On the positive side, Mr. Wilson commended the recreation department for picking up the trash in the beach lot.

“They are keeping it really clean, which it wasn’t in the past. Now that they are charging for parking, they are paying a little more attention,” he said.

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