🎶 Live Music Around Winter Haven: January 29 – February 3 🎶
Winter Haven is turning up the volume with a packed lineup of live music to close out January and kick off February. From local favorites and country vibes to a major charity event and intimate lounge sessions, there’s something for every music lover this week.
🎸 Korey Ketchum Music
Fans of acoustic and country sounds can catch Korey Ketchum at two popular local spots this weekend:
Friday, Jan. 30 – The Twisted Prop Bar & Grille, 6–9:30 p.m.
Saturday, Jan. 31 – Happenings Sports Pub with Joey Foley, 7–10 p.m.
🍻 Raise the Bar – Lake Alfred
Friday Night (Jan 30) – Mark Connors Music, 8–11 p.m.
1504 Lake Alfred Road, Lake Alfred, FL
*Located just on the edge of Winter Haven. This spot is perfect for a late-night live music fix.
🎤 Cypresswood Pub
Cypresswood Pub continues its strong run of live entertainment with a full weekend of music:
Thursday, Jan. 29 – Casey Howell Duo, 6–9 p.m.
Friday, Jan. 30 – Prime Country, 6–9 p.m.
Saturday, Jan. 31 – Blind Ambition, 6–9 p.m.
1099 Clubhouse Rd in Winter Haven
🎶 Tanners Lakeside – Charity Event
Saturday, Jan. 31, 2026 – Straight Up Boutlaw 2 Homecoming & Family Reunion
Tanners Lakeside will host a special live music charity event benefiting the Ronald McDonald House. The event features live music, food trucks, raffles, giveaways, and more, all in support of a great cause. A perfect way to enjoy live entertainment while giving back to the community.
1006 S Lake Howard Dr in Winter Haven
🍸 Sage Sessions at Sage Cocktail Lounge
Sage Sessions continues its popular weekly music series:
Every Tuesday Tuesday, Feb. 3 – Laura the Singer, 6–9 p.m.
Enjoy a relaxed evening of live music, cocktails, and great vibes at Sage Cocktail Lounge, located at
99 3rd Street NW, Winter Haven, FL 33881
Whether you’re looking for a lively weekend crowd, a meaningful community event, or a laid-back Tuesday night soundtrack, Winter Haven’s live music scene has you covered. 🎵
