Brooksville Holiday Events

Friday Night Live- November 2026

205 E. Fort Dade Ave., Brooksville, FL, United States, Florida 34601 13 Nov 2026

Christmas on Main

20 N Main St, Brooksville, FL 34601-2800, United States 5 Dec 2026

Mama's Whoopie Pies at Brooksville Main Street Christmas on Main

20 N Main St, Brooksville, FL 34601-2800, United States 5 Dec 2026

Downtown Street Market- November 2026

101 S Brooksville Ave, Brooksville, FL 34601-3310, United States 21 Nov 2026

Small Business Saturday

Historic Downtown Brooksville, Florida 28 Nov 2026

The Pumpkin Carving King

13009 Cortez Blvd., Brooksville, FL 34613 30 Oct 2026

Merry Driftmas Holiday Drift Festival at Lead Foot City (Dec 19, 2026)

17109 Old Ayers Rd, Brooksville, FL, United States, Florida 34604 19 Dec 2026

Night of Lights: Victorian Christmas Party

601 Museum Ct, Brooksville, FL 34601-2631, United States 11 Dec 2026

Community Yard Sale - Spring Ridge

14133 SWEETSHRUB COURT, Brooksville, FL, United States, Florida 34613 7 Nov 2026

Movie Night- Polar Express

Tom Varn Park 19 Dec 2026

Family Sensory Christmas Celebration

205 E. Fort Dade Ave., Brooksville, FL, United States, Florida 34601 18 Dec 2026

Everything must go yard sale!

19478 Sweet Pea Ln., Brooksville 34601 30 Oct 2026

Community Dedication Ceremony for the Dr. Dennis Wilfong Memorial Sleigh

20 N Main St, Brooksville, FL 34601-2800, United States 19 Nov 2026

8th Annual Florida Cracker Christmas

Jack Daniel's Amphitheatre at Florida Cracker 5 Dec 2026

Little Worlds: Reindeer Retreat

624 Erin Way Brooksville FL 34601 1 Dec 2026

HOLIDAY OPEN HOUSE

14430 Cortez Blvd, Brooksville, FL, United States, Florida 34613 19 Dec 2026

Christmas Party

7318 Sunshine Grove Rd., 34613 19 Dec 2026

DIY Decoupage Christmas Ornament Class

Artisan Haven BVL 15 Nov 2026

SOLO/LIVE MUSIC - Southern Hills Plantation Club - Brooksville, FL

Southern Hills Plantation Club 10 Dec 2026