Travel Sweepstakes in Baltimore, MD: Updated 2026 List for Local Winners
Photo: Germar Derron / Pexels
See the one active option Baltimore residents can enter, its exclusions, deadlines, and safer entry checks.
As of August 10, 2026, no verified Baltimore-only travel-package sweepstakes is currently open. Baltimore residents can enter one nearby promotion, but its prize includes festival tickets—not transportation or lodging. A sweepstakes is a free, chance-based promotion.
Here, "local winners" means Baltimore residents are eligible to win; it does not mean a Baltimore winner is assured.
The only current nearby opportunity
Ocean City's Beach & Boots sweepstakes runs through August 31, 2026. Maryland residents age 18 or older qualify, including people who live in Baltimore. The Mayor and City Council of Ocean City sponsors the promotion, while Ocean City Tourism administers it.
The Beach & Boots contest rules also list nine other eligible jurisdictions. Four winners are expected to be selected around September 8. Each winner receives two tickets to the Country Calling Festival, scheduled for October 2–3 in Ocean City.
The stated value is $550 per ticket pair. According to Ocean City Tourism's June 25 announcement, the odds depend on the total number of eligible entries received.
What the prize does—and does not—cover
Beach & Boots is useful for Baltimore readers who want festival admission and can arrange their own trip. It should not be treated as a travel-package sweepstakes. The prize excludes: Those costs could materially affect the prize's practical value.
Before entering, consider whether you could attend on the fixed October dates and pay the trip expenses yourself.
- Transportation between Baltimore and Ocean City
- Hotel or other lodging
- Parking
- Food and drinks
- Taxes
How Baltimore residents can enter
Baltimore residents may submit one online entry per person through August 31. Start at Ocean City Tourism's official Beach & Boots entry page. An additional promotional activation is scheduled at the Baltimore Orioles' Camden Yards on August 18.
The rules do not make attendance at that event necessary for the standard online entry. Before submitting, check these points:
- You are at least 18 years old.
- Your primary residence is in an eligible jurisdiction, including Maryland.
- You have not already used your one permitted entry.
- You could attend the October 2–3 festival if selected.
- You can cover all travel-related costs excluded from the prize.
Which Baltimore-area promotions have ended?
Visit Baltimore's B-Side Winter Staycation was a genuine local travel prize for Maryland residents. It included two hotel nights and city attractions, with an approximate value of $1,706, but entries closed January 25, 2026, according to the Visit Baltimore promotion rules. The Maryland Lottery's Ocean City Beachfront Getaway also offered travel-related value: a two-night resort stay plus $600.
However, the Maryland Lottery says entries closed July 7 and the drawing occurred July 8, 2026. Another open promotion from the Orioles and T. Rowe Price runs through September 20.
Its prizes are Orioles merchandise and tailgate gear, so it does not belong on a current travel-sweepstakes list.
How to screen prize notices safely
Legitimate sweepstakes do not require payment to enter, improve your odds, or collect a prize. The FTC's sweepstakes guidance identifies requests for money or financial information as warning signs. If you receive a winning notice: For the current Beach & Boots promotion, winners still bear transportation, lodging, parking, food, taxes, and incidental costs.
- Compare it with the sponsor and administrator named in the rules.
- Confirm that you entered the promotion.
- Do not pay a fee, tax, shipping charge, or processing cost to release the prize.
- Use the sponsor's published website rather than contact details supplied only in the message.
- Remember that valid travel expenses excluded by the rules are different from a demand to pay before receiving a prize.