The Cannonball Run Is Back: Here's What To Know & How To Win $25,000

Summer has a way of slipping by too quickly, but one of the Lake's biggest community events is ready to send the season out in style.

The second annual Cannonball Run returns to Lake of the Ozarks Aug. 22-29, 2026, bringing together boaters, businesses, live entertainment, family activities, and plenty of chances to win cash—all while raising money for local charities.

Last year's inaugural event generated 793 poker hands, more than $500,000 in local spending, attracted 65+ sponsors, and donated more than $88,000 to organizations throughout the Lake area.

The event's theme is simple: shop local, have fun, and win big.

Here's everything you need to know.

How the Cannonball Run Works

Registration costs $125 and includes:

One poker hand
One raffle ticket
Entry into prize drawings

Registered participants can then earn additional poker hands by shopping at Lake-area businesses between Aug. 22-29. For every $500 spent locally, participants receive another poker hand, with a maximum of 40 additional hands.

Even better, purchases made at participating sponsor businesses count double toward the total. View all the sponsors here.

Eligible purchases include:

Restaurants
Gas stations
Retail stores
Marinas
Hotels
And nearly any business in Camden, Miller, or Morgan counties

Receipts must:

Be dated Aug. 22-29
Include the business name
Include the participant's name
Prepaid lodging receipts may also qualify if they show the dates of the stay.

Participants must be 18 or older.

Register for the Cannonball Run here.

Win Big While Shopping Local

The more receipts participants collect, the more poker hands they can earn.

Hands will be drawn at 2 p.m. and 7 p.m. on Aug. 29 at Captain Ron's. The first collection will start at 9 a.m., and participants must be in line by 1:30 p.m. The second collection will start at 2 p.m., and participants must be in line by 6:30 p.m. The announcements of both winners will follow around 7 p.m.

Prizes include:

$25,000 for each Captains Collection receipt challenge winner
$5,000 minimum for the Land & Water Poker Run champions
Additional cash prizes and raffle drawings

The maximum poker hand consists of seven cards. In the event of a tie, prize money will be divided equally among winners.

The Cannonball Run Organization also reserves the right to administer a polygraph examination if necessary to verify receipt authenticity.

Week-Long Event Schedule

Saturday, Aug. 22

Kick-Off Concert

The Cannonball Run begins with a concert at Captain Ron's featuring:

Parmalee
Special guest Cole Goodwin

Time: Noon to 5 p.m.

via Parmalee Facebook

Get tickets here. General admission starts at $33.85, with the opportunity to also purchase a dock pass, pit pass, or beach access.

Sunday, Aug. 23

Water Olympics

Captain Ron's beach turns into an afternoon of friendly competition featuring:

Paddleboard races
Kayak races
Cardboard boat races

Time: 11 a.m. to 4 p.m.

Participants compete for prizes while helping raise money for local charities. Register now.

Wednesday, Aug. 26

Beginning Wednesday and continuing through Saturday, visitors can enjoy free parking all day at Scallywag's RV Park and browse the Vendor Village at Captain Ron's, featuring a variety of local businesses and vendors during select hours.

Thursday, Aug. 27

Sea Hag Fun Run

This boating poker run, which starts with breakfast at 9 a.m. at Captain Ron's, sends participants around the Lake with stops at:

Bear Bottom
Big Dick's Halfway Inn
Bulldogs
Nauti Fish
Red Fox
Lamplighter Resort
Patriot's Point Marina

Then return to Captain Ron's.

Time: 11 a.m. to 5 p.m. Drawings are from 4-6:30 p.m. Participants must be in line by 6 p.m.

Grand Prize: $5,000 cash

Every participant is also entered to win a ½-ounce gold coin ("Gold Doubloon") courtesy of Duncan Diamonds.

Register for the Sea Hag fun run. The $75 ticket covers the boat and driver, who will receive a poker hand, swag bag, and t-shirt. Additional riders and hands can be purchased.

Benefit Auction & Live Music

Following the Sea Hag Fun Run, Captain Ron's hosts a charity auction beginning at 6 p.m. The ChristiAna Band performs at 7 p.m.

Captain Ron's aerial (LakeTV).jpg — default

Friday, Aug. 28

Land Lubbers Poker Run

Prefer to stay on land? Participants will visit:

Nauti Dough Co.
Shell's Pasta
Tavern Smokehouse
Tres Hombres
The Branding Iron
Chevy's Bar & Grill

Then return to Captain Ron's.

Time: 11 a.m. to 5 p.m. Drawings are from 4-6:30 p.m. Participants must be in line by 6 p.m.

Grand Prize: $5,000 cash

Participants are also entered into a Gold Doubloon drawing.

Register your vehicle, which includes a poker hand, swag bag, and t-shirt. Extra riders, t-shirts, and poker hands are an additional purchase.

Saturday, Aug. 29

Car Show

The Cannonball Run Car Show begins with registration from 9-10 a.m., with the show running from 9 a.m. to 3 p.m. Judging is scheduled for 11 a.m. to 1:30 p.m., followed by awards at 2:30 p.m., including the People's Choice Award. In addition to showcasing vehicles, attendees can enjoy live entertainment, swag bags for participants, a silent auction, and 50/50 drawings throughout the day.

Pre-register now and save $5 on the day of the show.

Sandcastle Building Contest

Families can also head to Cannonball Beach for the Sandcastle Building Contest from noon to 3 p.m. on Saturday. Participants will compete for prizes, bragging rights, and the chance to show off their creativity in the sand.

Register to build sandcastles for $20, sponsored by Shawnee Bend Sand.

Yamaha WaveRunner Raffle

The excitement continues later that afternoon with the WaveRunner Raffle, featuring a 2025 Yamaha JetBlaster and single-person trailer. The drawing will take place at 5 p.m., with tickets available for $20 each or six for $100. Proceeds from the raffle benefit the Laurie-Sunrise Beach Rotary Club.

Buy raffle tickets.

Supporting the Lake Community

While the Cannonball Run offers substantial cash prizes, organizers say the event's biggest purpose is giving back. After prize payouts, proceeds support numerous Lake-area charities and organizations, including:

Northwest Fire Protection District
Sharing and Caring Foundation
Laurie-Sunrise Beach Rotary
Raising Butterflies
Livabilities
Dream Factory
Lake West Chamber of Commerce
Central Ozarks Medical Center (COMC)
FF 14/17 Volunteer Fire Department
Lakers Baseball
Lake of the Ozarks Watershed Alliance (LOWA)
Citizens Against Domestic Violence (CADV)
Osage Community Lodge #2705

Whether you're shopping local for extra poker hands, cruising the Lake during the Sea Hag Fun Run, enjoying live music, or simply cheering on contestants from the beach, the Cannonball Run offers a full week of entertainment while supporting organizations that make a difference throughout the Lake area.

Registration, ticket information, sponsor lists, and event details are available at cannonballrunatcaptainrons.com. Visit Captain Ron's on the 34.5 Mile Marker or 82 Aloha Ln in Sunrise Beach.