Sweepstakes in Chesapeake, VA: Updated 2026 List for Local Winners

Chesapeake's active sweepstakes scene right now centers on one recurring local drawing and one statewide program open to every resident. Chesapeake Pawn & Gun's weekly giveaway accepts new entries every Tuesday, while the Virginia Lottery's Rewards program lets any enrolled player in the city redeem points toward drawing entries or free play. Several other Chesapeake-specific sweepstakes ran in 2025 and 2026, but their entry windows have already closed.

This list separates what a Chesapeake resident can still enter today from what already ended, so you don't spend time chasing a promotion that's no longer live.

Verification note: Program terms and availability can change. This page was checked against linked sources on October 27, 2026.

The Weekly Giveaway Still Taking Entries

Chesapeake Pawn & Gun, located at 3330 S Military Hwy, runs an ongoing weekly giveaway through its own website. Entrants must be at least 21 years old and may submit one entry per person each Tuesday, according to the store's giveaway page. The store announces a winner every Thursday at 11 a.m.

Eastern time. Recent prizes have included a Springfield Armory Hellcat OSP and a SIG Sauer P320 Compact, both picked up in person at the Chesapeake store. Because the giveaway resets weekly, it's the one program on this list that's reliably open on any given week.

Check the page directly before entering, since the specific prize and entry mechanics can change from one week to the next.

A Statewide Program Every Chesapeake Resident Can Join

Beyond single-business giveaways, Chesapeake residents also have access to the Virginia Lottery's Rewards program, which runs statewide. Any player who enrolls can earn points through regular lottery activity and redeem them toward entries in lottery drawings or toward free-play credit, according to the Virginia Lottery's Rewards FAQ. Unlike the Chesapeake Pawn & Gun giveaway, this isn't a single drawing with one winner — it's an ongoing points system managed through the valottery.com account or the Virginia Lottery app's "Redeem Points" feature.

That makes it a steadier option for anyone who already plays, rather than a one-time chance at a specific prize. It's a state program, so it carries the same rules for every Virginia resident, not just those in Chesapeake. It's included here because it's genuinely usable by anyone in the city right now, which can't be said for most of the location-specific promotions below.

Local Sweepstakes That Have Already Closed

Chesapeake Bank marked its 125th anniversary with a "Shop Local 125" sweepstakes. Every customer who held a Chesapeake Bank debit card during August 2025 was automatically entered, and the bank drew 25 winners at random for a $125 gift card to a local small business of their choice, according to Chesapeake Bank's sweepstakes page. Winners were notified in September 2025, and no newer round of the promotion has appeared since.

Separately, Audacy's WPTE-FM "The Point" gave away four tickets to the Chesapeake Jubilee festival at Chesapeake City Park, held May 14 through 17, 2026. The station took phone entries from May 4 through 8, 2026, with up to five winners selected, sponsored by Dreamland Amusements, according to Audacy's contest page. Both of these show what a Chesapeake-specific sweepstakes typically looks like: tied to a local business or event, open for a short window, and not recurring on a fixed schedule.

Neither is something you can enter today.

Why a Chesapeake-Only List Looks Thin Right Now

Most sweepstakes tied specifically to Chesapeake are short, dated promotions rather than ongoing programs. The Chesapeake Bank anniversary draw and the WPTE Jubilee giveaway each opened around a specific event or milestone, then closed for good once that window passed. That pattern means a genuinely "currently active" Chesapeake list leans on recurring small-business giveaways, like Chesapeake Pawn & Gun's weekly drawing, and statewide programs like Virginia Lottery Rewards, rather than one-off sweepstakes with large prizes.

If you're looking for a big-prize local sweepstakes to enter this week, most of those have already run their course for 2026.

How to Confirm an Offer Is Still Open Before You Enter

Local giveaways change terms, prizes, and deadlines often, so confirm the current details directly with the sponsor rather than relying on a secondhand list. A few steps make that quick: Checking the sponsor's own rules each time is the most reliable way to know whether a Chesapeake sweepstakes is still accepting entries.

• Go to the sponsor's own page — Chesapeake Pawn & Gun's giveaway page or the Virginia Lottery's Rewards FAQ — rather than a search result or a summary.
• Check the entry window and any age or residency requirement before submitting information.
• Note how and when a winner is announced, so you know whether to expect a call, an email, or an in-store pickup.
• If a promotion tied to a specific event or anniversary shows no visible "next round" announcement, treat it as closed rather than assuming it repeats annually.

Frequently Asked Questions

Is there a sweepstakes in Chesapeake, VA that's open for entries right now?

Yes. Chesapeake Pawn & Gun runs a weekly giveaway taking entries every Tuesday with a winner announced Thursdays at 11 a.m. Eastern, according to the store's giveaway page.

Can Chesapeake residents use the Virginia Lottery Rewards program?

Yes. Any enrolled player statewide, including Chesapeake residents, can redeem points toward lottery drawing entries or free-play credit through the valottery.com account or app.

Is the Chesapeake Bank "Shop Local 125" sweepstakes still running?

No. It covered debit card holders during August 2025 only, with winners notified in September 2025, and no newer round has been announced.

What about the Chesapeake Jubilee ticket giveaway?

That giveaway from WPTE-FM "The Point" took phone entries from May 4 to 8, 2026, for the festival held May 14-17, 2026. The entry window has closed.