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.
