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OSCEOLA, IA (August 31, 2026) – Lakeside Hotel & Casino in Osceola is kicking off September with its inaugural Car Show on Monday, September 7, bringing classic cars, food trucks, music and more than $2,500 in cash prizes to the property. This month’s lineup also includes Saturday night bands, Song Blast Dueling Guitars performance and dining specials throughout the month.
September events and deals include the following:
Events
September 7 – Inaugural Lakeside Car Show: Lakeside Hotel & Casino will host its first-ever Car Show from 10 a.m. to 4 p.m., featuring classic cars, food trucks, local vendors and live music. Registration begins at 9 a.m. and there is no entry fee. Four awards will be presented, including:
1st Place – Chrome and Glory: $1,500 cash and trophy
2nd Place – Garage Legend: $750 cash and trophy
3rd Place – Clean Machine: $250 cash and trophy
4th Place – Head Turner: Trophy
For more information, contact Amber at amestan@affinitygaming.com or (641) 414-7725.
Live Performances
September 5 – Willie Mac & The Lost Cousins: Enjoy an evening of music and dancing as Willie Mac & The Lost Cousins take the stage during Lakeside's weekly Live Music Saturday series in the Sports Lounge from 8 p.m. to 11 p.m. Admission is complimentary.
September 12 – Josh Sinclair: Spend Saturday night enjoying the musical stylings of Josh Sinclair in the Sports Lounge from 8 to 11 p.m. Admission is free.
September 12 – Song Blast Dueling Guitars: Song Blast Dueling Guitars is coming to Lakeside Hotel & Casino at 7:30 p.m. for an energetic musical showdown featuring two talented guitarists going head-to-head on some of the audience’s favorite songs. With plenty of energy, passion and audience interaction, the show promises an entertaining evening for music fans of all kinds.
Tickets are priced at $24.73 including taxes and fees.
September 19 – GARRETT & THE RELICS: Enjoy an evening of live music with fan-favorites from GARRETT & THE RELICS in the Sports Lounge from 8 to 11 p.m. Admission is complimentary.
September 26 – Hat Trick: Close out the month with Hat Trick in the Sports Lounge from 8 to 11 p.m. No cover charge is required.
October 9 – Peter Antoniou: Peter Antoinou from America’s Got Talent brings his psychic comedian show to Lakeside Hotel & Casino at 7:30 p.m.
Tickets are now on sale for $30.44 including taxes and fees.
Dining Specials
West Lake Bar & Grill: Visitors can indulge in comforting culinary favorites throughout the month, including:
Mondays: Beef Pot Pie for $18 or complimentary with 100 base points earned.
Sunday through Thursday: Pulled Pork Sandwich for $16 beginning at 4 p.m., while supplies last.
Buffet Offerings: Visitors can enjoy the following weekly specials:
Fridays: Friday Buffet for $18.95 from 4 p.m. to 10 p.m.
Saturday Breakfast Buffet - $14.95 from 9 a.m. to 10:30 a.m.
Saturday Dinner Buffet - $22.95 from 4 p.m. to 10 p.m.
Sunday Bunch: $21.95 from 9 a.m. to 2 p.m. Champagne and mimosas are also available to complete the weekend experience.
Food & Beverage Free Play Offer: Patrons who spend $30 in food and beverage can receive $10 in Free Play. Attendees must present their West Lake Bar & Grill receipt and A-Play® Card at the Guest Service Center to receive the offer. The promotion is available once every 24 hours and is not valid if the purchase was made with points or comps.
