WV’s H​​ollywood Casino At Charles Town Offers New Penn Play Loyalty Rewards Program

Written By Hill Kerby on May 4, 2025
Penn Play Rewards Hollywood Casino

The patrons of Hollywood Casino at Charles Town Races have recently been enrolled in a fresh loyalty program.

At the start of May, Penn Entertainment, the parent company of Hollywood Charles Town, introduced its new rewards program, Penn Play, to all 43 of its properties nationwide.

Patrons from Nevada to the east coast can now enjoy earning rewards while engaging in various activities such as playing, dining, shopping, and even online gambling at Penn’s mobile sportsbooks and casinos. This exciting opportunity extends to all of Penn’s properties and brands, including Hollywood, Ameristar, Barstool, and many others, totaling around a dozen options.

Continue reading to learn more about Penn Play’s launch and how you can win $1.5 million in prizes and cash rewards.

Out with the old, in with the new

When Penn Play acquired Pinnacle Gaming in 2018, it decided to replace the existing mychoice Loyalty Rewards program with its own program.

Introducing the new program, Penn Cash, where players can now redeem their rewards throughout all of Penn’s brands and properties, just like earning them. Additionally, a brand-new website and app have been launched, allowing players to conveniently register and instantly earn $50 in Penn Cash.

  • You can receive $10 by downloading the Penn Play rewards app.
  • You will receive $15 when you connect your Penn Play account to a slot or table game using the app.
  • When you create a Penn Wallet account, you will receive $25 in Penn Cash.

In addition, Penn is holding extra drawings until June 6, offering the chance to win hundreds of thousands of dollars.

  • Throughout the month of May, we will be conducting daily drawings where we will select 100 lucky winners. Each winner will have the opportunity to win up to $2,000 in Penn Cash.
  • Every week, 100 additional winners have the chance to win up to $25,000 in Penn Cash. On top of that, the winners from fifth to first place will also be rewarded with 25,000 Choice Hotels points. To make it even more exciting, the first-place winner will receive a luxurious 7-day Norwegian Cruise Line cruise.
  • We are excited to announce the grand prize drawing which will take place on June 6th. In this drawing, an additional 100 lucky individuals will have the chance to win up to $100,000 in Penn Cash. Furthermore, the top five winners will be rewarded with 100K Choice Hotels points, while the ultimate grand prize winner will be treated to a luxurious Haven Cruise aboard the prestigious Norwegian Cruise Line.

More upgrades

Penn developed a marketplace within the latest application, enabling users to exchange gifts and receive rewards for in-app purchases. Additionally, the app will incorporate advanced 3 C’s technology, allowing for transactions without the need for physical cards, cash, or contact.

In addition, players will be able to enjoy sign-up incentives for the Penn Entertainment Mastercard, as well as exclusive benefits from Live Nation and Choice Hotels.

The updated program introduces five loyalty tiers: Play, Advantage, Preferred, Elite, and Owners Club.

Penn Heroes, formerly known as the myhero program, was ultimately rebranded. This program aims to pay tribute to the military, veterans, and first responders while offering them additional perks and discounts. As a part of the revamp, all program members are now entitled to an automatic tier upgrade.

Upcoming events at Hollywood Charles Town

Hollywood Casino at Charles Town Races not only offers a Vegas-inspired gambling experience but also boasts a renowned event center capable of accommodating 1,500 people. This venue has quickly established itself as a premier performance destination in the Washington-Baltimore area.

Events in May:

  • On Friday, May 12th at 8 p.m., get ready for the hilarious live comedy show, Fransquatch, featuring the comedic talents of Barstool Sports personalities Francis Ellis and Lil Sasquatch.
  • On Saturday, May 13 at 8 p.m., catch Christina P, a renowned stand-up comedian who has two Netflix specials and also serves as the host of the highly acclaimed podcast, Your Mom’s House.
  • Join us on Sunday, May 14 from 10 a.m. to 2 p.m. for the Mother’s Day Brunch Buffet at Skyline Terrace restaurant. Indulge in a delightful experience with live music, carving stations, delectable snow crabs, endless mimosas, and much more.
  • Thunderstruck: America’s AC/DC Tribute will be taking place on Saturday, May 20 at 9 p.m.
  • On Friday, May 26th at 8 p.m., witness the extraordinary tribute performance of Dean Z – The Ultimate Elvis.
  • Rob Schneider’s “I Have Issues Tour” is scheduled for Saturday, May 27 at 8 p.m.

The facility is aptly named as it includes a horse racing track where live races take place and off-track wagering is available.

Races are live on Thursdays, Fridays, and Saturdays, starting at 7 p.m. until the end of May and throughout the summer. Simulcast betting is offered from Wednesday to Sunday, with betting windows open from 11:30 a.m. until closing time, which varies between 6 p.m. and 11:15 p.m., depending on the day.

The Coin Collector Stakes, a 4 ½-furlong race with a $75,000 purse, will be hosted by the racetrack on Sunday, May 13. This race is just one of the 33 Stakes races scheduled on Charles Town’s calendar for 2025. Additionally, if you happen to be in the area on Wednesday nights, don’t miss Pour House Trivia Night at 7 p.m. inside the Barstool Sportsbook. Winners have the opportunity to receive up to $100 in food and beverage credit, while enjoying special deals such as half-off appetizers, discounted flatbreads, and a variety of drink specials.