Win a Street Glide
Win a Street Glide
The Street Glide is Harley's batwing bagger and, with the Road Glide, the motorcycle American sweepstakes give away more than any other. Dealers, charity raffles, apparel brands and bagger builders all put one up as the prize, which means an open Street Glide giveaway is rarely hard to find.
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Why win a Street Glide?
The fork-mounted batwing fairing is the silhouette most people picture when they hear the word Harley, and behind it sits a Milwaukee-Eight V-twin, hard bags, a low seat and an infotainment stack built for all-day highway miles. That mainstream pull is precisely why it is a giveaway staple: a dealer promotion, a veterans' charity raffle or an apparel brand can put one up knowing riders of every stripe will enter. Prizes run from a stock Street Glide or Street Glide ST through CVOs to shop-built customs on big front wheels with stretched bags and serious audio. Values follow the same spread — roughly $25k–$30k new, roughly $43k–$45k for a CVO, roughly $18k–$28k used — and a custom's build receipt usually runs well ahead of open-market resale. Because those figures sit far below what a prize car costs, the tax bill stays manageable and a cash alternative, where offered, often comes close to the bike's real value. Check each listing's spec sheet for the year, the engine and the mods, and look for a published free mail-in route before you spend a dollar on entries.
Winning a Street Glide — common questions
Which Street Glides get given away?
Everything from a stock Street Glide or ST put up by a dealer or a charity raffle to CVO Street Glides and fully built custom baggers out of the shop scene. The listing spec sheet shows the year, the engine and every modification.
Do you pay taxes if you win a Street Glide?
Yes — a won Street Glide is taxed as ordinary income at its fair market value, so plan for roughly a quarter to a third of it. On a bagger worth roughly $25k–$30k that is a manageable bill rather than a car-sized one. See our motorcycle giveaway taxes guide for the full breakdown.
Can I enter a Street Glide giveaway for free?
Yes — US sweepstakes law requires a free, no-purchase entry route where each free entry counts the same as a paid one, which we surface on each Street Glide listing where the operator publishes one.