In July 2016, Brent Rogers launched an ice cream truck in Sterling, Alaska, a Kenai Peninsula community with fewer than 90 registered businesses in the entire ZIP code. His youngest child was still in school. He named the operation after a pirate flag and called his kids Scallywags.
Five seasons later, around 2021, the mobile chapter closed. Rogers retired the neighborhood routes when that youngest child graduated high school, parked the truck, and moved the whole operation to a fixed address at 36297 Cottontree Ln, Sterling, AK 99672. Nearly a decade after its first summer, The Jolly Roger’s Taste of Paradise is still running.
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The Business Details
The Jolly Roger’s Taste of Paradise is a sole proprietorship owned and operated by Brent Rogers. The Better Business Bureau opened its file in March 2019 and has maintained an A+ rating on the business through 2026. Rogers handles everything directly and can be reached at (907) 394-0403.
The product lineup is straightforward:
- Pre-packaged ice cream bars and frozen novelties
- Popsicles and snack items
- Private party and event bookings
There are no soft serve machines, no hand-dipped cones. Pre-packaged frozen treats are the entire offering. That keeps the operation manageable within Alaska’s compressed seasonal window, where most food vendors on the Kenai Peninsula pull their entire annual revenue across four to five summer months.
For anyone looking to follow seasonal updates or get in touch, the business Facebook page runs under the handle @TJRScallywag.
The Story Behind the Pirate Name
The Jolly Roger is the name for the skull-and-crossbones pirate flag, and Rogers built that image into every corner of the brand. The Facebook handle, the truck name, the word “Scallywag” in the farewell announcement — none of it was accidental.
When Rogers told the community the mobile phase was ending, he wrote this on the business page:
“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 children were the Scallywags. The ice cream truck ran through the same years they were growing up on the Kenai Peninsula. When the youngest finished school, the mobile routes finished with him. By the time Rogers made that announcement, the Facebook page had built 819 likes and 38 check-ins from the Sterling area and broader Kenai Peninsula community.
The name was never just branding. It was a family clock.
Why Sterling Is the Right Place for This Business
Sterling looks small on paper. The ZIP code 99672 covers 63 square miles of land, holds 86 registered businesses, and has just 557 residential mailboxes. The commercial strip along the Sterling Highway runs to a Three Bears grocery store, a handful of fishing lodges, some bed and breakfasts, and not much else.
What Sterling does have is the Kenai River.
Travel Alaska, the state’s official tourism body, calls the Kenai River “the world’s greatest sportfishing river.” The U.S. Fish and Wildlife Service describes it as the most heavily used freshwater fishery in Alaska. The river holds the world record for King Salmon — a 97 lb 4 oz fish pulled from the water on May 17, 1985 by Les Anderson, a record that still stands. Annual sockeye returns regularly top 700,000 fish, and the river runs eight distinct salmon seasons from May through October.
Sterling sits on that corridor. The town is described by Travel Alaska as “a full-service community geared toward visitors preparing to venture into surrounding wilderness,” and the majority of summer tourists visiting Alaska head straight to the Kenai Peninsula. The Cottontree Lane address is minutes from Dots Landing, one of the most used public boat launches on the Kenai River. During the salmon runs, fishing guides, charter groups, and camping families move through that stretch of Sterling daily.
In a ZIP code with 86 businesses and a summer population that multiplies every May, a frozen treats vendor that close to the Kenai River covers a gap in the local food landscape that nothing else is filling.
Sterling residents’ median household income sits at $102,415, with a poverty rate of just 4.55% — a working, family-centered community with the money and the summers to make a local ice cream business viable year after year.
Booking the Jolly Roger’s Ice Cream Truck for a Party or Event
Party and event bookings have been part of The Jolly Roger’s Taste of Paradise since the truck launched. Rogers handles those requests directly, and the service extends to private gatherings across the Sterling area and surrounding Kenai Peninsula communities.
The business has appeared at local Sterling properties and community events, confirmed through references on area Facebook pages. For anyone putting together a summer birthday, a fishing lodge event, or a family gathering in the area, this is the contact to make:
- Phone: (907) 394-0403
- Facebook: @TJRScallywag
- Address: 36297 Cottontree Ln, Sterling, AK 99672
Visiting in 2026: What to Know Before You Go
Alaska runs on seasonal timing, and Sterling ice cream vendors follow it closely. Most operations in the area open between late April and mid-May, then close in September or early October based on weather conditions. Rogers has operated on this schedule since 2016.
Before making a trip to the Jolly Roger’s Taste of Paradise in Sterling, a quick call to (907) 394-0403 is the most reliable way to confirm current hours and availability. Alaska weather shapes schedules more than calendars do, and Rogers manages everything directly.
Sterling has about 7,000 year-round residents and a summer population that swells every June when the King Salmon run opens on the Kenai River. In that setting, a family-built frozen dessert business with a pirate name, an A+ BBB rating, and nine seasons behind it has carved out something most small Kenai Peninsula businesses never manage. The Jolly Roger’s Taste of Paradise has been part of Sterling’s summer fabric since 2016 — and in March 2026, it is still there on Cottontree Lane, a few minutes from the river, waiting for the season to begin.
