Upcoming Brooksville Events

Check out what's happening all around Brooksville, FL

Motown comes to Brooksville show/concert

 Sat, 11 Oct at 07:00 pm Sparacia Witherell Family Winery & Vineyard

3rd Annual EBA Road to the Finals

 Fri, 07 Nov at 05:30 pm Hernando County Fair Grounds

SOLD OUT: Sleepy Hollow Theme Tea Party

 Sat, 18 Oct at 07:00 pm 309 S Main St, Brooksville, FL, United States, Florida 34601

Downtown Street Market- October

 Sat, 18 Oct at 10:00 am 13 S Brooksville Ave, Brooksville, FL 34601-2905, United States

Tokyo Takeover Drift Fest at Lead Foot City

 Sat, 11 Oct at 06:00 pm 17109 Old Ayers Rd, Brooksville, FL, United States, Florida 34604

Trunk or Treat with a Firefighter

 Fri, 17 Oct at 05:00 pm 17240 Cortez Blvd, Brooksville, FL, United States, Florida 34601

Week 3 - 23rd Annual Brooksville Pumpkin Patch

 Fri, 17 Oct at 02:00 pm Brooksville Pumpkin Patch

Goth Prom Costume Party

 Sat, 25 Oct at 08:00 pm 500 S Broad St., Brooksville, FL, United States, Florida 34601

Marker 48 Brewing Annual Oktoberfest Featuring The Running of the Wieners

 Sat, 18 Oct at 02:00 pm 12147 Cortez Blvd, Brooksville, FL

Straight No Chaser in Brooks

 Fri, 21 Nov at 08:00 pm Cache Creek Casino Resort Event Center

Beasley Farms Fall Festival & Pumpkin Patch 🎃

 Sat, 25 Oct at 10:00 am 10137 Preston Road, Brooksville, FL, United States, Florida 34601

BROTHERS AGAIN (featuring the music of The Allman Brothers Band) LIVE! @ The Sparacia Winery

 Sat, 08 Nov at 07:00 pm Sparacia Witherell Family Winery & Vineyard

Friday Night Live- October 2025

 Fri, 10 Oct at 06:30 pm 205 E. Fort Dade Ave., Brooksville, FL, United States, Florida 34601

Annual Trunk or Treat

 Sat, 18 Oct at 06:00 pm 13470 Chambord St, Brooksville, FL, United States, Florida 34613

Christmas on Main- Tree Lighting and Festival

 Sat, 06 Dec at 03:00 pm 20 N Main St, Brooksville, FL 34601-2800, United States

The Fancy Flea Brooksville

 Sat, 01 Nov at 09:00 am 115 N Main St, Brooksville, FL 34601-2520, United States

Lea Salonga in Brooks

 Fri, 03 Oct at 09:00 pm Cache Creek Casino Resort

Blues/Rock Revival Festival Brooksville

 Sat, 08 Nov at 02:00 pm Sparacia Witherell Family Winery & Vineyard

Ultimate Coldplay Tribute @ Sparacia Witherell Family Winery

 Fri, 10 Oct at 06:00 pm Sparacia Witherell Family Winery & Vineyards, Snow Hill Road, Brooksville, FL, USA USD 30 to 47

The American Stones @ Sparacia Witherell Winery (Rolling Stones Tribute)

 Sat, 22 Nov at 06:00 pm Sparacia Witherell Family Winery & Vineyards, Snow Hill Road, Brooksville, FL, USA USD 30 to 47

Downtown Street Market- November

Sat, 15 Nov at 10:00 am 13 S Brooksville Ave, Brooksville, FL 34601-2905, United States

HarvestMoon Fun Farm Fright Nights

 Sat, 04 Oct at 07:00 pm 15990 Stur St, Masaryktown, FL, United States, Florida 34604

TRUNK OR TREAT

Sat, 25 Oct at 04:00 pm Edison Ink & Company

👻 Spooky Bingo Night + Costume Contest 🎃

 Fri, 24 Oct at 06:00 pm 134 E Fort Dade Ave, Brooksville, FL, United States, Florida 34601

Sunset Moth & Glass Coffin Crafting Class ⚰️

 Sat, 11 Oct at 06:30 pm 291 E Jefferson St, Brooksville, FL 34601-2699, United States

Halloween & Fall Fest - Week 5 - 23rd Annual Brooksville Pumpkin Patch

 Fri, 31 Oct at 02:00 pm Brooksville Pumpkin Patch

Derina Harvey Band in Brooks

 Wed, 26 Nov at 07:30 pm Griffin Park School

Small Business Saturday

 Sat, 29 Nov at 10:00 am Historic Downtown Brooksville, Florida

Spooky Spectacular Fall Festival

 Sat, 18 Oct at 09:00 am Chinsegut Conservation Center

Family Sensory Christmas Celebration

 Fri, 19 Dec at 05:00 pm 205 E. Fort Dade Ave., Brooksville, FL, United States, Florida 34601

Art & Oddities Night Market at Broad Street Brewing

 Sat, 11 Oct at 05:00 pm 291 East Jefferson street , Brooksville, FL, United States, Florida 34601

🍂 Fall Simmers Class at Artisan Haven 🍂

 Sun, 05 Oct at 01:00 pm 134 E Fort Dade Ave, Brooksville, FL, United States, Florida 34601

Colt Ford & The Lacs - Florida Cracker Dirt Road Anthem Concert in Brooksville

 Sat, 25 Oct at 06:00 pm Jack Daniel's Amphitheatre at Florida Cracker

Brooksville Tangerine Festival

 Sat, 07 Feb at 11:00 am 20 N Main St, Brooksville, FL 34601-2800, United States

TRIBUTE TO DOKKEN - INTO THE FIRE

 Sat, 20 Dec at 07:00 pm Sparacia Witherell Family Winery & Vineyards USD 30 to 47

Hernando Hustle 5K Walk & Run

 Sat, 18 Oct at 07:30 am Tom Varn Park

3rd Annual “Blues On The Hilltop” Music Festival

 Sat, 15 Nov at 12:00 pm Sparacia Witherell Family Winery & Vineyards USD 25 to 53

Live Music at the Post!

Sat, 04 Oct at 06:00 pm 12091 Cortez Blvd, Brooksville, FL, United States, Florida 34613

Trick or Treating at the Brooksville Pumpkin Patch

 Fri, 31 Oct at 06:00 pm Brooksville Pumpkin Patch

Rockstar Lobster🦞 at Sparacia Winery

 Sat, 11 Oct at 04:00 pm Sparacia Witherell Family Winery & Vineyard

Colt Ford at Florida Cracker Kitchen

 Sat, 25 Oct at 06:00 pm Florida Cracker Kitchen

Friday Night Live- November 2025

 Fri, 14 Nov at 06:30 pm 205 E. Fort Dade Ave., Brooksville, FL, United States, Florida 34601

Moonborn Book Release Party with Author Sarah Moore

Sat, 25 Oct at 06:00 pm 309 S Main St, Brooksville, FL, United States, Florida 34601

The Snowball Shack Presents: Halloween Movie Night!

 Fri, 10 Oct at 06:30 pm 7298 Sunshine Grove Road, Brooksville, FL

Pumpkin Chuckin at the Brooksville Pumpkin Patch

 Sat, 01 Nov at 01:00 pm Brooksville Pumpkin Patch

Fall-elujah Fair

 Sat, 18 Oct at 03:00 pm 17125 Citrus Way , Brooksville, FL, United States, Florida 34614

The Halloween Costume 🎤

Fri, 17 Oct at 07:00 pm Taipei Taipei Tea House

Paint Night at Citrus & Sage! NEW ART ALERT!

 Thu, 23 Oct at 06:00 pm Citrus & Sage Bookshop

Track-or-Treat Drag Racing Halloween Monster Fest, Wrestling, Power Wheels

 Sat, 25 Oct at 04:00 pm Lead Foot City USD 126,272

John Holmes 50K, 16M, 9M Trail run

 Sat, 04 Oct at 07:00 am Tucker Hill

Essential Oil Workshop with Catrina

 Sat, 08 Nov at 06:30 pm 309 S Main St, Brooksville, FL, United States, Florida 34601

Brooksville Food Trucks & Wine Festival

 Sat, 13 Dec at 01:00 pm 21509 Snow Hill Road, Brooksville, FL

Fall Wine Glass Painting at Masaryk Winery by The Boozy Bookworm

 Fri, 10 Oct at 06:00 pm Masaryk Winery

Sumter Swap Meets in Brooksville FL

 Sun, 05 Oct at 07:30 am 5360 Lockhart Rd, Brooksville, FL

Halloween Howl & HCSO Safety Fun Fest

 Sat, 25 Oct at 04:00 pm 20 N Main St, Brooksville, FL 34601-2800, United States

Week 1 - 23rd Annual Brooksville Pumpkin Patch

 Fri, 03 Oct at 02:00 pm Brooksville Pumpkin Patch

Networking & Expansion Event

 Sat, 04 Oct at 11:00 am 1681 E Jefferson St USD 0 to 55

ASB at Broad Street Brewing Co

Fri, 17 Oct at 06:00 pm Broad Street Brewing Co.

Party Because We Want To

 Sat, 25 Oct at 08:00 am 309 S Main St, Brooksville, FL, United States, Florida 34601

Tunnel of Terror®: Tommy's Express Brooksville

 Fri, 17 Oct at 06:00 pm 13406 Cortez Blvd, Brooksville, FL 34613-6822, United States

Appreciation is Brewing

 Fri, 17 Oct at 10:00 am Inland Homes at Cascades at Southern Hills Free

A Night in Prythian: Paint & Trivia Event at Citrus & Sage Bookshop in Brooksville with Sam!

 Sat, 15 Nov at 07:00 pm Citrus & Sage Bookshop

Trunk or Treat

 Thu, 23 Oct at 05:00 pm 7411 Cortez Oaks Blvd, Brooksville, FL, United States, Florida 34613

Day of the Dead Ceremony

Sat, 01 Nov at 06:00 pm 9 N Georgia Ave, Brooksville, FL, United States, Florida 34601

5th Annual MONSTER Fest Halloween Trunk-or-Treat Car Show, Drag Racing, Haunted Walk & Family Fun!

 Sat, 25 Oct at 04:00 pm 17109 Old Ayers Rd, Brooksville, FL, United States, Florida 34604

🎃🍪 Halloween Cookie Decorating with Jen Whayman 🍪🎃

 Fri, 17 Oct at 06:00 pm 134 E Fort Dade Ave, Brooksville, FL, United States, Florida 34601

Sandal Key Fall Festival

 Sat, 18 Oct at 10:00 am 10318 Whitehurst St, Brooksville, FL 34613-3910, United States

Thursday Night Song Writers Workshop

 Thu, 09 Oct at 07:00 pm 316 W Jefferson St, Brooksville, FL

Autostock Southern Showdown

 Sat, 04 Oct at 10:00 am Whitehead Farms

10 a.m. Chinsegut Hill Tour

 Sat, 04 Oct at 10:00 am 22495 Chinsegut Hill Road, Brooksville, FL, United States, Florida 34601

TRUCKS & TASTES EVENT

 Thu, 09 Oct at 06:30 pm The Hardware Store,115 N. Main Street, Brooksville, Florida

Bourbon, Beer, and BBQ

 Thu, 09 Oct at 06:00 pm Marker 48 Brewing

Tool Making: Witch's Broom - Tool for Cleansing & Protection

 Sat, 18 Oct at 05:30 pm 9 N Georgia Ave, Brooksville, FL, United States, Florida 34601

Beasley Farm’s Fall Festival & Pumpkin Patch!

Sat, 11 Oct at 10:00 am 10137 Preston Road, Brooksville, FL

Petsmart Adoption Day Spring Hill

Sat, 04 Oct at 12:00 pm Downtown Brooksville

Posability’s Moms Retreat

 Fri, 07 Nov at 05:00 pm Chinsegut Hill Retreat and Conference Center

Tarot Social Group Event: Used Deck Swap!

 Sat, 04 Oct at 11:00 am 9 N Georgia Ave, Brooksville, FL, United States, Florida 34601

Torching with a Twist presents FALL themed classes! At Broad street brewery!

Sat, 18 Oct at 05:00 pm Broad Street Brewing Co.

Beyond the Apron Strings- Class 4 Pickling

Thu, 09 Oct at 07:00 pm 624 Erin Way, Brooksville FL 34601

Fantasy Book Club

 Thu, 09 Oct at 07:00 pm 309 S Main St, Brooksville, FL, United States, Florida 34601

Dueling Pianos

 Sat, 22 Nov at 06:00 pm 2248 Culbreath Rd, Brooksville, FL, United States, Florida 34602

Torching with a Twist presents FALL themed classes! At Broad street brewery!

Sat, 04 Oct at 05:00 pm Broad Street Brewing Co.

BBQ at the THRIFT STORE Brooksville

 Sat, 11 Oct at 10:00 am Mike's Used Furniture and More Thrift Store

10.24.25 Grateful Pumpkin Paint and Sip at Sparacia Witherell Winery

 Fri, 24 Oct at 07:00 pm Sparacia Witherell Family Winery & Vineyard

A FREE Trunk or Treat Event!

 Fri, 31 Oct at 06:00 pm 475 North Avenue West, Brooksville, FL, United States, Florida 34601

Pop-up Charm Bar + Workshop

 Fri, 14 Nov at 06:00 pm Citrus & Sage Bookshop

Gabby's Dollhouse

 Sat, 04 Oct at 10:00 am 12961 Cortez Blvd, Brooksville, FL 34613

The Second Annual South BooVille Avenue Halloween Stroll

 Sat, 25 Oct at 04:00 pm Brooksville water tower

District Game - HHS Varsity Leopards Football VS. Weeki Wachi HS Hornets

 Fri, 24 Oct at 07:30 pm Hernando High School: Leopard Pride

GriefShare

 Thu, 09 Oct at 06:00 pm 420 Howell Ave, Brooksville, FL, United States, Florida 34601

Week 2 - 23rd Annual Brooksville Pumpkin Patch

 Fri, 10 Oct at 02:00 pm Brooksville Pumpkin Patch

Open Mic at Broad Street Brewing

Wed, 08 Oct at 06:30 pm 291 East Jefferson street , Brooksville, FL, United States, Florida 34601

Hernando High School Class of 2005 20-Year Reunion

 Sat, 04 Oct at 06:00 pm The Treiman House USD 50

Week 4 - 23rd Annual Brooksville Pumpkin Patch

 Fri, 24 Oct at 02:00 pm Brooksville Pumpkin Patch

Victorian Crow Party - 2nd Annual! 🐦‍⬛

 Sat, 04 Oct at 06:00 pm 9 N Georgia Ave, Brooksville, FL, United States, Florida 34601

Florida's Adventure Coast Sip & Savor Celebration

 Fri, 24 Oct at 05:00 pm Legacy Lane Weddings

Beasley Farm Fall Festival and Pumpkin Patch 🎃

 Sat, 18 Oct at 10:00 am 10137 Preston Road, Brooksville, FL, United States, Florida 34601

Park Takeover: Movie Edition

 Fri, 17 Oct at 06:00 pm Tom Varn Park

Anime Auto-Con Tokyo Takeover - Drift Festival at Lead Foot City

 Sat, 11 Oct at 02:00 pm Lead Foot City USD 126,272

Reign Conference 2025

 Wed, 08 Oct at 07:00 pm 14494 Cortez Blvd, Spring Hill, FL, United States, Florida 34613
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