Brent Rogers started with a truck, a pirate theme, and five summers of neighborhood routes. Here is the full picture heading into 2026.
The Jolly Roger’s Taste of Paradise is a frozen treats business in Sterling, Alaska, owned and operated by Brent Rogers. It launched as a mobile ice cream truck on July 30, 2016, ran neighborhood routes across the Kenai Peninsula for five summers, then moved to a fixed address at 36297 Cottontree Lane, Sterling, AK 99672. As of early 2026, the business is still active, still taking party bookings, and still operating the same pre-packaged ice cream and popsicle model it has used since day one.
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Quick Facts: The Jolly Roger’s Taste of Paradise
| Owner | Brent Rogers |
| Address | 36297 Cottontree Ln, Sterling, AK 99672 |
| Phone | (907) 394-0403 |
| @TJRScallywag | |
| Party Bookings | Available — call or message directly |
| BBB Rating | A+ (file opened March 2019, no complaints on record) |
| Entity Type | Sole Proprietorship |
| Founded | July 30, 2016 |
| Operating Season | Spring through fall — call ahead to confirm hours |
Is the Jolly Rogers Ice Cream Truck Still Open in Sterling?
Yes. As of October 2025, the business appears in Yelp’s updated ice cream listings for three separate markets: Sterling, Soldotna, and Kenai. The BBB profile is active. The Facebook page at @TJRScallywag is still the primary point of contact for seasonal updates and private event bookings. Rogers is sole owner and handles all inquiries directly.
It is a seasonal operation, as most food businesses in this part of Alaska are. The opening window typically runs from late spring through early fall. If you are visiting from outside the area, call (907) 394-0403 before making the trip.
The Name Tells the Whole Story
Most small business names are forgettable. This one has a layer most people walk right past.
“Jolly Roger” is the skull-and-crossbones pirate flag — one of the most widely recognized symbols in popular culture. But Rogers is also Brent Rogers’ actual last name. The business name is a pun on his own family name, built in from the beginning. “Taste of Paradise” leans into the same pirate-island theme, rounding out an identity that is entirely intentional.
The branding carries all the way through. Rogers referred to his children as his “Scallywags” — pirate slang for a rascal, used here as an affectionate family nickname. The Facebook handle for the business is @TJRScallywag (The Jolly Rogers Scallywag). When the mobile chapter eventually ended, the reason given tied directly back to those same kids.
Every part of the brand is the family. That was never a coincidence.
Five Years Mobile, Then a Permanent Home
From 2016 to roughly 2021, the truck ran regular routes through Sterling’s residential neighborhoods and took bookings at community events across the Kenai Peninsula. For five consecutive summers, residents along the Sterling Highway corridor knew when to listen for it.
The Better Business Bureau opened a file on the business in March 2019 and issued an A+ rating, which has remained unchanged.
When the mobile operation wound down, Rogers said it plainly in a post on the business’s Facebook page:
“The Jolly Rogers ice cream truck is settled in at it’s new home! We will miss seeing all of your smiling faces, and delivering sweet treats throughout the ‘hoods! Our final Scallywag graduates high school this week, so it was time for a change. We want to thank all of our Peninsula Peeps for all of your support over the past 5 years! We are grateful and blessed.”
His youngest child finishing high school was the reason. The mobile routes stopped on his own timeline, tied to a family milestone. The business itself did not close. It settled at 36297 Cottontree Lane and kept going.
What the Jolly Rogers Sells
The product line is deliberately simple. There are no soft-serve machines, no hand-dipped scoops, and no made-to-order items.
What’s on offer:
- Pre-packaged ice cream bars
- Popsicles
- Frozen novelties and snacks
This model worked on the truck because it requires no specialized equipment and holds well in a mobile environment. At the fixed location, it keeps overhead low and service fast. The business also offers private event and party bookings, a service that has been used by local Kenai Peninsula businesses looking to add a frozen treats option to community gatherings.
Why This Business Works in Sterling, Alaska
Sterling sits along the Sterling Highway in Kenai Peninsula Borough, about 11 miles northeast of Soldotna. The Kenai River runs along the community’s southern edge before flowing west to Cook Inlet.
Every summer, the river draws anglers from across the country and around the world. The Alaska Department of Fish and Game records an average of 313,000 angler days per year on the Kenai River going back to 1977. The agency identifies it as the largest freshwater sport fishery for sockeye and king salmon in the state. Salmon season runs from May through October, overlapping almost exactly with the ice cream season.
Sterling itself, according to the 2020 U.S. Census, has a population of 5,918, up from 4,705 in 2000. The median household income as of 2023 is approximately $107,000, well above the Alaska state median, with families making up a strong share of the resident base. The community borders the Kenai National Wildlife Refuge, and the Sterling Highway carries heavy summer traffic from Anchorage heading south toward Homer.
For a seasonal frozen treats business, the combination of high-income local families, summer fishing tourism, and highway foot traffic is about as favorable a market as you will find in rural Alaska.
Where Things Stand in 2026
The Jolly Roger’s Taste of Paradise is approaching ten years in operation. The A+ rating from the Better Business Bureau has not moved. The business continues to appear across Kenai Peninsula ice cream searches on Yelp. The Facebook page remains the live point of contact.
There are not many sole-proprietorship food businesses in Alaska that make it a decade while operating seasonally. The ones that do tend to have something the others don’t: a reason for people to seek them out by name.
Contact and Booking Information
The Jolly Roger’s Taste of Paradise
Location: 36297 Cottontree Ln, Sterling, AK 99672
Phone Number: (907) 394-0403
Facebook: @TJRScallywag
For current hours, seasonal opening dates, and private event availability, contact Brent Rogers directly by phone or through the Facebook page. This is a seasonal operation — confirming ahead of a visit is always worth it.
