Win a 2026 Harley-Davidson Street Glide, a Road Glide, or $10,000 Cash

What you're playing for

This is a three-way choice, not a package: the winner picks a 2026 Harley-Davidson Street Glide, a 2026 Road Glide, or $10,000 in cash. One prize, one winner, and the decision is yours.

The Street Glide is the headline bike and the one the fund leads with. It is the second model year of the redesigned Grand American Touring platform, which means the liquid-cooled-head Milwaukee-Eight 117 is standard rather than a CVO-only indulgence — 105 horsepower at 4,600 rpm and 130 lb-ft of torque at 3,250, through a six-speed and a belt. The redesign also brought a 12.3-inch Skyline OS touchscreen with Apple CarPlay, all-LED signature lighting, cornering ABS, traction control and vehicle hold control, and a Batwing fairing Harley genuinely developed in a wind tunnel instead of styling by eye.

The Road Glide is the same drivetrain behind the frame-mounted Sharknose fairing. That single difference is the whole argument: the Street Glide's fairing turns with the bars and feels lighter at parking-lot speed, while the Road Glide's sits on the frame and stays planted when you are three hours into an interstate crosswind. Riders have taken sides on this for forty years, and neither side is wrong.

Why it matters

The Cape & Islands Police K-9 Relief Fund is not a sweepstakes company that rents a car for a photo shoot. It is a South Dennis, Massachusetts nonprofit that pays veterinary bills for retired police dogs on Cape Cod and the Islands — the ones whose costs land on a handler's personal budget the day the dog stops being a department asset. The fund has been doing this for two decades, has local press coverage going back years, holds a chamber membership, publishes a phone number and an email address, and carries federal EIN 04-3768613 (registered under the name Cape Cod Police K-9 Relief Fund). The bikes come through Cape Cod Harley-Davidson, whose logo sits on the ticket page.

That matters because most "win a Harley" pages you will encounter online are anonymous storefronts. This one has a named organization, a named dealer, a named cause and a decade-plus paper trail behind it. It also has a real ceiling on your odds, because the fund describes the ticket count as limited — a $100 raffle ticket in a small local pool is a genuinely different proposition from a $20 entry in an unlimited national sweepstakes.

The fine print worth knowing

This is a raffle, not a sweepstakes, and that changes the rules. Massachusetts charitable raffles run under a municipal permit and are purchase-required by design — there is no "no purchase necessary" alternate entry, because the statute that makes a charity raffle legal is the same one that makes buying a ticket the only way in. If you are used to sweepstakes mail-in routes, do not go looking for one here. Tickets are $100 each, and the checkout lets you take up to 25 in a single order.

Read the trim name carefully. The fund's raffle page advertises a "Street Glide Special," but the checkout page and Harley's own 2026 catalog both say plain Street Glide — the Special suffix was retired when the bike was redesigned for 2024. It is almost certainly stale marketing language rather than a different motorcycle, but the specific trim, color and accessory package on the bike that has actually been ordered are not published anywhere, and that is what separates a $27,000 bike from a $33,000 one.

The checkout page is thin on disclosures. It carries the prize, the price and a quantity selector, and not much else: no drawing date, no printed ticket cap, no eligibility terms, no official rules and no Massachusetts raffle permit number. None of that is unusual for a small local fundraiser on a ticketing platform, but it does mean the answers live with the organization rather than on the page. The fund's annual Motorcycle Run — the event at which its bike raffle has historically been pulled, at the end of the ride — is set for Saturday, September 26, 2026, running from Patriot Square in South Dennis to MacMillan Wharf in Provincetown. If you want the drawing date confirmed before you spend, ask them: 508-294-1869, or info@capecodpolicek9.org.

Taxes. Two separate things, and people mix them up. Buying a raffle ticket is not a deductible charitable contribution under IRS rules, no matter how good the cause — the chance to win is what you received in exchange. And if you win, the prize is reportable income at its fair market value, so a $33,000 motorcycle arrives with a tax bill attached and no cash in the box to cover it. That is a real part of the $10,000-versus-the-bike calculation, along with registration, title, insurance and getting it home.