Best Contest Alerts in Chesapeake, VA: 2026 Local Guide

The best contest alert for Chesapeake, VA readers right now is WTKR News 3's "Pro Pigskin Pick'em," a free, no-purchase NFL pick'em contest running through the 2026 regular season and open to anyone in the station's viewing area, which covers Chesapeake. It pays out weekly and feeds into a season-long grand-prize drawing, making it the one verified contest you can enter today. Beyond that single active program, Chesapeake's contest landscape runs on short, event-tied windows: a photo contest, a few radio ticket giveaways, and a standing sweepstakes page that cycles through regional events.

This guide walks through what's currently open, what recently closed and why it still matters, and where to look next for a fresh local giveaway.

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

What's Actually Open Right Now

As of late October 2026, WTKR's Pro Pigskin Pick'em contest is the only confirmed, currently running contest available to Chesapeake residents. WTKR is the CBS affiliate serving Hampton Roads, and its contest page states the pick'em runs through the regular NFL season with no entry fee. Entry works through a single online account.

According to WTKR's official rules, each entrant registers once, picks winners for the week's NFL games, and can change those picks up until a given game's kickoff. One point is awarded per correct pick, and whoever scores highest that week wins. Ties are not left to chance alone.

The same rules page explains that a tiebreaker uses a guessed combined score for that week's Monday Night Football game, and if entrants are still tied after that, a random drawing decides the winner. There's a second layer worth knowing about: every weekly winner also earns an entry into a season-long grand-prize drawing, stacking small weekly wins into a shot at a bigger prize later in the season.

How to Claim a Prize if You Win

Winning is only half the process — claiming matters just as much, and WTKR's rules are specific about the window. Per the official rules, the registered account holder must claim any prize online within 30 days of the relevant game, and WTKR does not mail prizes. That means a winner needs to log back into the account used to enter, not a new one, and complete the claim themselves rather than through a friend or family member.

The station may also require identification before releasing a prize, so having ID ready speeds up the process. Missing the 30-day window appears to forfeit the prize, based on how the rules are written, so treat the claim step as part of winning rather than an afterthought.

Why Several Other Chesapeake-Area Contests Have Already Closed

Not every local contest worth knowing about is still open, and understanding why helps set expectations for the rest of this year. The Chesapeake Bay Foundation ran its annual "Save the Bay" photo contest from March 9 through March 27, 2026, open to photographers age 13 and up across the whole Bay watershed, including Chesapeake. Per the Chesapeake Bay Foundation's contest page, winners received cash prizes between $100 and $500 and had their photos featured in CBF's 2026 calendar and in Bay Journal magazine.

That window has already closed for this year. A similar pattern shows up with local radio giveaways. Audacy's Hampton Roads stations — 95.7 R&B, Z104, Point Radio, and 2WD — ran three separate ticket giveaways for the Hampton Jazz & Music Festival between May 26 and June 12, 2026, each one closing within days of airing.

Per Audacy's contest page, winners received two- or four-ticket packs worth roughly $75 for the June 26-28 show at Hampton Coliseum. Chesapeake had its own version of this. Point Radio and 2WD ran an on-air call-in giveaway for four tickets per winner to the Chesapeake Jubilee, the city's own spring festival at Chesapeake City Park, from May 4 through May 8, 2026, ahead of the May 14-17 event.

Details are on Audacy's Chesapeake Jubilee contest page. These examples are closed, but they show that the same stations and the same foundation reliably run contests tied to their annual events — meaning similar opportunities should return around the same events next year.

Where to Check for the Next Local Opportunity

Because most Chesapeake-area contests outside the WTKR pick'em run on short, one- to two-week windows tied to a specific concert or festival, no fixed list stays accurate for long. The most reliable approach is checking a small number of pages directly rather than relying on a static roster. WVEC/13News Now maintains a standing sweepstakes page that has run contests tied to regional events in prior years, even though no 2026-dated entry period could be confirmed as open as of this writing.

That track record is still useful: it tells you the station's format exists and is worth checking again when a major regional event is announced.

• WTKR's contest page, where the Pro Pigskin Pick'em currently lives, for any new contest the station launches
• The Audacy Hampton Roads station pages (95.7 R&B, Z104, Point Radio, 2WD) for on-air giveaways tied to upcoming concerts or festivals
• WVEC/13News Now's sweepstakes section, which has previously run entries tied to events like the Hampton Roads International Auto Show and Something in the Water

Quick Eligibility Checklist Before You Enter

A few details apply across these local contests and are worth confirming before you enter anything:

• Residency: Chesapeake falls within WTKR's viewing area and Audacy's Hampton Roads broadcast footprint, so location-based eligibility for these specific programs is already met for local readers.
• Age: the CBF photo contest requires entrants to be 13 or older; other contests may carry their own minimum ages in their official rules.
• Account requirements: WTKR's pick'em requires one registered account per entrant — creating multiple accounts to get extra entries isn't how the contest is structured.
• Deadlines move fast: radio station giveaways close within days, so if a festival or concert is coming up in Hampton Roads, check the relevant station's page before the event rather than after it's announced.
• No purchase necessary differs from free: entering WTKR's pick'em costs nothing, but confirm any prize's claim requirements — like the 30-day online claim window — before assuming a win is automatic.

Frequently Asked Questions

Is there an entry fee for WTKR's Pro Pigskin Pick'em?

No. WTKR's contest page describes it as a no-entry-fee contest open throughout the regular NFL season.

Can I still enter the Chesapeake Bay Foundation photo contest or the Hampton Jazz Festival giveaways?

No, both have closed for 2026 — the photo contest ran March 9-27 per CBF's page, and the jazz festival giveaways ran May 26-June 12 per Audacy's contest page.

What happens if I win Pro Pigskin Pick'em but don't claim my prize in time?

The official rules state prizes must be claimed online within 30 days of the relevant game, and WTKR does not mail prizes, so missing that window appears to forfeit the claim. See the official rules for details.