events & deals you can't miss
Explore the many events and travel deals happening on Florida’s Adventure Coast, Brooksville-Weeki Wachee-Hernando Beach. From farmers markets in historic Brooksville, to Front Porch Art Walks in Hernando Beach, you’ll find local events, festivals, concerts and experiences for all ages. Visitors can experience a vibrant calendar of festivals, shows, and signature events happening year-round.
Don’t miss out—explore our Annual Events & Festivals!
Don’t see your event? DOWNLOAD OUR GUIDE to find out how to promote your upcoming event!
Upcoming Events to Discover in Brooksville, FL
Static event cards remain readable before the live widget becomes interactive.
Nov 20 @ 7:00 PM - 9:00 PM EST | 309 S Main St, Brooksville, FL 34601, USA
Paint Night at Citrus & Sage Bookshop! Christmas Raven!
Join us for some new art! We have our Christmas Raven! All supplies included!This is a non refundable class. Please arrive at least ten minutes prior to check in.
Explore eventMultiple Dates | Stage West Playhouse
The Game’s Afoot
A fast-paced holiday whodunit in which Broadway star William Gillette, famous for playing Sherlock Holmes, investigates a dangerous mystery during a holiday party. Performances...
Explore eventNov 21 @ 6:00 AM - 2:00 PM EST | 11060 Northcliffe Blvd, Spring Hill, FL 34608, USA
Sherwood Florist's Annual Christmas Open House - Celebrating 40 years!
It’s our 40th year in business, and we’re celebrating in a BIG way! Join us for a magical holiday experience inspired by Charles Dickens’ A Christmas Carol as we kick off the Ch...
Explore eventNov 21 @ 8:00 AM EST | 15 S Broad St, Brooksville, FL 34601, USA
2026 Tunnel to Towers Brooksville 5K Run & Walk
Join us for the 4th Annual Tunnel to Towers Brooksville 5K Run & Walk on Saturday, November 21st, 2026, at Brooksville Commons as we come together to Run. Walk. Honor. this incr...
Explore eventNov 21 @ 9:00 AM - 2:00 PM EST | Hernando County Fairgrounds
Regal Railways Presents Model Train Show & Sale
Regal Railways Presents Model Train Show/Sale Saturday November 21, 2026 Hernando Fairgrounds 6436 Broad Street Brooksville, FL 34601 Over 70 tables of vendors will be on hand s...
Explore eventMultiple Dates | Field of Dreams Car Show
Annual Field of Dreams Car Show 2026
Annual Field of Dreams Car Show 2026 Field of Dreams Car Show Saturday & Sunday, November 21st & 22nd, 2026 All proceeds to benefit Shriners Hospitals for Children Spectator ent...
Explore eventNov 21 @ 10:00 AM - 2:00 PM EST | Historic Downtown Brooksville
Downtown Street Market- November 2026
CALLING ALL BESTIES: IT'S FRIENDSGIVING DOWNTOWN! As the season of gratitude approaches, it’s time to step back in time and celebrate friendship, nostalgia, and classic small-to...
Explore eventNov 21 @ 5:00 PM - 9:00 PM EST | 9 N Georgia Ave, Brooksville, FL 34601, USA
Free Open Mic Night in Brooksville | Music, Poetry, Comedy & More
Join us for a FREE Open Mic Night at The Artist’s Realm in downtown Brooksville!On Saturday, November 21st from 5:00–9:00 PM, The Artist’s Realm is opening its doors for a relax...
Explore eventNov 21 @ 6:00 PM - 10:00 PM EST | 21509 Snow Hill Road, Brooksville, FL 34601
Beer For My Horses - Toby Keith Tribute @ Sparacia Witherell Family Winery
We’re Going Country. We’ve Got The Red Solo Cups & We’re Gonna Be Filling Them Up. Saturday, November 21st! Check-In Starts @ 6pm.
Explore eventNov 21 @ 6:00 PM - 10:00 PM EST | Timber Pines Performing Arts Center
Chas Collins
Find tickets for Chas Collins at Timber Pines Performing Arts Center in Spring Hill on 11/21/2026 at 6:00 PM
Explore eventNov 23 @ 1:00 PM - 4:00 PM EST | The City of Praise
The City of Praise 4th Annual Community Thanksgiving Dinner
Join us for our 4th Annual Community Thanksgiving Dinner. Come and gather, give thanks, and Fellowship together! Everyone is Invited!
Explore eventNov 26 @ 8:00 AM - 9:15 AM EST | Anderson Snow Park
THE STARFISH FOUNDATION TURKEY TROT 5K
A Thanksgiving Day 5K and 1-mile fun run/walk at Anderson Snow Park supporting the STARFISH Foundation in Hernando County. Participants receive a race shirt and finisher medal,...
Explore eventNov 26 @ 8:00 AM EST | Tom Varn Park
Brooksville Kiwanis Turkey Trot
Thanksgiving morning 5K and 1-mile fun run for all ages and fitness levels. The event includes timed and family-friendly race options, with proceeds benefiting the Shop With a C...
Explore eventMultiple Dates | 85 Myers Rd, Brooksville, FL 34602, USA
Thanksgiving Bluegrass Festival 2026
Bring a lawn chair for Seating in the concert areas. We will have a Thanksgiving Pot Luck dinner on Thursday afternoon for all campers in the park. Turkey will be provided. Brin...
Explore eventMultiple Dates | Bowl 360 Strike City Spring Hill
Ashley Lux Band
ALB performing modern Pop, Rock & Dance We're an engaging, energetic band that is currently performing both original and cover songs. We were born and raised in NY and are now l...
Explore eventNov 28 @ 10:00 AM - 2:00 PM EST | Historic Downtown Brooksville
Small Business Saturday
Small Business Saturday: Shop the Heart of Brooksville! Saturday, November 28th 10:00 AM – 2:00 PM Downtown Brooksville (South Brooksville Ave & Liberty Street) This holiday...
Explore eventNov 28 @ 6:00 PM - 9:45 PM EST | Sparacia Witherell Family Winery & Vineyards
The Pure Zeppelin Experience @ Sparacia Witherell Family Winery
Get Ready To Rock Brooksville! 2nd Annual Thanksgiving Weekend w/ The Pure Zeppelin Experience. Ultimate Tribute To: LED ZEPPELIN!
Explore eventDec 4 @ 6:00 PM - 10:00 PM EST | 21509 Snow Hill Road, Brooksville, FL 34601
The Sting Police @ Sparacia Witherell Family Winery (The Police Tribute)
GET READY TO ROCK BROOKSVILLE! Sting & The Police Tribute Show makes its way to Sparacia Witherell Winery. Friday, Dec. 4th. - Check-In @ 6.
Explore eventDec 5 @ 2:00 PM - 3:00 PM EST | 9 N Georgia Ave, Brooksville, FL 34601, USA
Creative Writing Workshop with Joy Bergman
Learn the magic of Creative Writing with Joy Bergman, a #1 Amazon author!Joy is a #1 Amazon author of "Our Perspective", as well as a Jerry Jazz Musician Short Fiction Finalist,...
Explore eventDec 5 @ 2:00 PM - 4:00 PM EST | Spring Hill United Church of Christ
Holiday Concert Series - Saturday
Holiday Concerts - Save the date. Saturday 10/10/26 Spring Hill United Church of Christ and Sunday 10/11/26 Nativity Lutheran Church.
Explore eventDec 5 @ 2:00 PM EST | Spring Hill United Church of Christ
Weeki Wachee Winds Holiday Concert
Holiday concert by the Weeki Wachee Winds community wind ensemble.
Explore eventDec 5 @ 3:00 PM - 9:00 PM EST | Historic Downtown Brooksville
Christmas on Main
SAVE THE DATE: THE MAGIC RETURNS TO MAIN STREET! Mark your calendars! The most enchanting night of the year is officially on the horizon. Brooksville Main Street, alongside our...
Explore eventDec 5 @ 5:30 PM EST | 4242 Lake in the Woods Drive, Spring Hill, FL, United States, Florida 34607, 4242 Lake in the Woods Dr, Spring Hill, FL 34607-2501, United States
OMG It's Wicks and Friends in The Venue at OM
Tickets are ALMOST SOLD OUT! GET YOUR FLIP PHONES READY We are over-the-moon excited to announce that Omgitswicks and friends will be performing at The Venue At OM on Saturday,...
Explore eventDec 5 @ 6:00 PM - 10:30 PM EST | 966 East Jefferson Street, Brooksville, FL 34601
8th Annual Florida Cracker Christmas
Celebrate the 8th Annual Florida Cracker Christmas on 12/5 with Pam Tillis, Lorrie Morgan & Darryl Worley live in Brooksville!
Explore eventDec 6 @ 10:00 AM - 2:00 PM EST | 4242 Lake in the Woods Drive, Spring Hill, FL, United States, Florida 34607, 4242 Lake in the Woods Dr, Spring Hill, FL 34607-2501, United States
Om Grown Market: Your Local Farmer’s Market! 🌿
Om Grown Market: Your Local Farmer’s Market! Hosted by: Wellcome OM & Om Grown Community Garden Dates: Sunday, December 6th (Outdoor)Time: 10:00 AM – 2:00 PM Location: Wellc...
Explore eventDec 6 @ 10:30 AM - 1:30 PM EST | VFW Post 8681
DIECASTARAMA - December 6, 2026
Family-friendly diecast-model show featuring new releases, classic models, vendor tables, Hot Wheels customs, and information about making custom cars.
Explore eventDec 6 @ 2:00 PM - 4:00 PM EST | Nativity Lutheran Church of Weeki Wachee
Holiday Concert Series - Sunday
Holiday Concerts - Save the date. Saturday 10/10/26 Spring Hill United Church of Christ and Sunday 10/11/26 Nativity Lutheran Church.
Explore eventDec 10 @ 2:00 PM - 3:30 PM EST | East Hernando Meeting Room, East Hernando Branch
Holidays in Huckleberry: A Cozy Mystery Event @ East Hernando Branch
An interactive holiday cozy-mystery activity set during a fictional Christmas window and cookie stroll. Participants read clues and solve the case at their own pace while enjoyi...
Explore eventDec 11 @ 6:00 PM - 9:00 PM EST | May-Stringer House
Night of Lights: Victorian Christmas Party
Step right up for an evening of Victorian Christmas magic at the historic May-Stringer House! Marvel at twinkling holiday décor, wander through a beautifully decorated Victorian...
Explore eventDec 11 @ 6:00 PM - 9:45 PM EST | 21509 Snow Hill Road, Brooksville, FL 34601
Sounds Of Simon & Garfunkel @ Sparacia Witherell Family Winery
National Touring Act: Sounds Of Simon & Garfunkel RETURN to Sparacia Witherell Winery. Friday, December 11th.
Explore eventDec 12 @ 8:00 AM - 5:00 PM EST | Hernando Beach Yacht Club
Annual Hernando Beach Christmas Boat Parade Supporting Toys for Tots
A holiday boat parade hosted by Hernando Beach Yacht Club. Decorated boats and boaters gather to celebrate the season and support Toys for Tots through new, unwrapped gift donat...
Explore eventDec 12 @ 9:30 AM EST | Hernando Park, 205 E Fort Dade Ave, Brooksville, FL, United States
Yoga in Hernando Park
FREE YOGA in Hernando Park. Second Sunday of every month through May. Join us under the trees in a gentle flow to start the day.
Explore eventDec 13 @ 10:00 AM - 3:00 PM EST | Staples – Spring Hill
Staples Christmas Car Show
A holiday car show welcoming all vehicles, with judged categories, trophies, DJ music, vendors, food trucks, raffles, and toy-drive participation. Judged entries cost $20 plus a...
Explore eventDec 13 @ 12:00 PM - 5:00 PM EST | 14311 Spring Hill Dr, Spring Hill, FL 34609, USA
Christkindlmarket Grove Market at Tidal Brewing
We look forward to celebrating the holidays with our Grove Market family for our 9th annual Christkindlmarket event! See you all soon, friends 🤍💙🩵 Since 2018, we have teamed up...
Explore eventDec 17 @ 12:00 PM - Dec 20 @ 12:00 PM EST | Stage West Playhouse
Candy Cane Chaos #2
A high-spirited youth holiday show presented by Stage West Playhouse, featuring festive comedy, seasonal fun, and family-friendly entertainment.
Explore eventDec 18 @ 10:30 AM - 11:30 AM EST | Main Library
Holiday Edition Walk & Talk for Adults @ Main Library
A one-mile guided walk focused on Brooksville’s local history, historic buildings, and Christmas decorations. The walk begins and ends at the Main Library; registration is requi...
Explore eventDec 18 @ 5:00 PM - 9:00 PM EST | Hernando Park
Family Sensory Christmas Celebration
A GENTLE GLOW & CANDY-COATED MAGIC: THE 4th ANNUAL FAMILY SENSORY CHRISTMAS CELEBRATION Brooksville, imagine a holiday celebration where the lights are soft, the music is a...
Explore eventDec 18 @ 5:30 PM - Dec 19 @ 9:00 PM EST | South Brooksville Avenue, Brooksville, FL, USA
The Fifth Annual South Brooksville Avenue Christmas Stroll
🎄 Fifth Annual South Brooksville Avenue Christmas Stroll 🎄 📅 December 18th & 19th, 2026 | 🕔 5:30 PM - 9:00 PM 📍 South Brooksville Avenue Historic District Join us for a heartwar...
Explore eventDec 19 @ 10:00 AM - 3:00 PM EST | WellCome OM
The Once Upon an OM Winter Faire
A holiday-season winter faire with a fantasy and Renaissance theme, featuring more than 75 local artisans, makers, and wellness vendors, plus food, live entertainment, games, fa...
Explore eventDec 19 @ 10:00 AM EST | Brooksville Cemetery
Wreaths Across America
A remembrance ceremony at Brooksville Cemetery honoring veterans who served the country. Participants may attend the ceremony, volunteer to lay wreaths, or sponsor a wreath.
Explore eventDec 19 @ 4:00 PM EST | Tom Varn Park
Movie Night- Polar Express
A holiday movie night at Tom Varn Park featuring a screening of The Polar Express and family-oriented Christmas entertainment.
Explore eventDec 31 @ 7:00 PM - 1:00 AM EST | The Water Tower, Downtown Brooksville
NYE Tangerine Ball Drop 2026
A free New Year’s Eve street party under Brooksville’s historic Water Tower, featuring a night market, food from downtown restaurants and food trucks, live music, a children’s c...
Explore eventJan 2 @ 7:00 AM - 5:00 PM EST | Tucker Hill
Croom Zoom 50K, 20M, & 10M
January 2, 2027 The Croom ZOOM 50K/20M/10M courses uses the extensive trails of Croom Park. The trails wind through oak hammocks on a well-defined trail that takes runners throu...
Explore eventJan 9 @ 12:00 PM - 5:00 PM EST | Hernando County YMCA
3 KINGS DAY FESTIVAL / Festival de los 3 Reyes (5th Annual)
3 KINGS DAY FESTIVAL IN SPRING HILL (5th Annual) Festival de los 3 Reyes en Spring Hill Saturday, Jan 9th, 2027 @ Hernando County YMCA.
Explore eventMultiple Dates | 5360 Lockhart Rd, Brooksville, FL 34602, USA
Florida Gulf Coast Clusters Dog Show
FOR INFORMATION CALL 813-928-2022 Over 250 breeds to be seen Many days for Obedience & Rally (check schedule) Numerous Specialty shows throughout the week Vendor Chair: Judy Sel...
Explore eventJan 14 @ 10:00 AM - Jan 17 @ 11:00 AM EST | 85 Myers Rd, Brooksville, FL 34602, USA
HangCon 2027
HangCon.com The largest hammock hang in the region.
Explore eventMultiple Dates | Stage West Playhouse
She Loves Me
A romantic musical about two shop clerks who dislike each other while unknowingly falling in love through anonymous letters. The production is presented by Stage West Playhouse...
Explore eventJan 16 @ 10:00 AM - 3:00 PM EST | Hernando County Fairgrounds
Booksville Festival Volume 3: Mythology
The 3rd annual Booksville Festival is coming back to Brooksville!With activities and adventures geared for the entire family, you'll experience several ways to celebrate the joy...
Explore eventJan 16 @ 10:00 AM EST | Masaryk Winery, 19121 Phillips Rd, Masaryktown, FL, United States
Masaryk Wine Run 5k
Like Running or Walking? Love Wine? This race is for you! Join us on Saturday, January 16, 2027 at 10:00am for an exciting event that features the scenic views of Masaryk Winery...
Explore eventJan 16 @ 12:00 PM EST | Florida Classic Park
Pasco Florida Kennel Club
AKC dog show: Pasco Florida Kennel Club in Brooksville, FL, January 16, 2027. Hosted by Pasco Florida Kennel Club. View judges, location, and entry info.
Explore eventJan 23 @ 6:30 PM - 8:30 PM EST | 2248 Culbreath Rd, Brooksville, FL 34602, USA
Dueling Pianos Dinner & Show
It’s not too early to put this on your calendar, so get your tickets now before they sell out!! This is our second annual dueling pianos. Last year was such a hit, everyone lov...
Explore eventJan 30 @ 4:45 PM EST | 4139 Shoal Line Blvd, Hernando Beach, FL 34607, USA
Hernando Beach's FIRST Offshore Murder Mystery Dinner Show with Riddlesbrood Touring Theater Company
🏴☠️ ONLY 15 SEATS AVAILABLE! 🏴☠️ Start the New Year with a little murder, mystery and mayhem on the Gulf! Join us aboard the Marina Rose for Hernando Beach’s FIRST offshore Mu...
Explore eventJan 30 @ 7:00 PM - 9:00 PM EST | Stage West Playhouse
Dueling Pianos
An interactive concert featuring Florida Premier Pianos, with live song requests, comedy, audience participation, and music ranging from classic rock and country to pop, Broadwa...
Explore eventFeb 4 @ 10:00 AM - Feb 6 @ 11:45 PM EST | 85 Myers Rd, Brooksville, FL 34602, USA
Antemesaris 36 - The Peoples Party
https://www.facebook.com/groups/587248248030147/media
Explore eventFeb 6 @ 11:00 AM - 6:00 PM EST | 20 N Main St, Brooksville, FL 34601-2800, United States, 20 N Main St, Brooksville, FL 34601-2800, United States
Tangerine Festival
SQUEEZE THE DAY AND SAVE THE DATE FOR THE 3rd ANNUAL BROOKSVILLE TANGERINE FESTIVAL! Brooksville Main Street is beyond thrilled to announce the most vibrant, zestiest, and most...
Explore eventFeb 6 @ 1:00 PM - 8:00 PM EST | 9 N Georgia Ave, Brooksville, FL 34601, USA
Brush Rust! | A Speed-Painting Showdown at The Artist's Realm
The Artist's Realm is excited to introduce Brush Rush!, a brand-new speed-painting competition coming to Downtown Brooksville on February 6, 2027!We're putting a new spin on tra...
Explore eventFeb 17 @ 10:00 AM - Feb 20 @ 11:45 PM EST | 85 Myers Rd, Brooksville, FL 34602, USA
Whippersnap Music And Arts Festival 2027
Whippersnapfest.com
Explore eventMultiple Dates | Stage West Playhouse
Social Security
A comedy about adult children dealing with aging parents and the well-meaning chaos that follows. The production is presented by Stage West Playhouse under arrangement with Conc...
Explore eventMultiple Dates | Linda Pedersen Park
Weeki Wachee Swampfest
Celebrate authentic Florida fun at the Weeki Wachee Swamp Fest! This family-friendly festival features live entertainment, arts and crafts vendors, delicious food and plenty of...
Explore eventMar 8 @ 5:30 PM - 9:30 PM EST | Bayport Inn
Nature Coast Parrot Head Club Phlocking
From the Midwest to the South and performing on cruise lines to the Caribbean, Bahamas, Mexico and the Panama Canal, singer and musician Mike Archer (who prefers to just be call...
Explore eventMar 12 @ 9:00 AM - Mar 14 @ 11:00 AM EDT | 85 Myers Rd, Brooksville, FL 34602, USA
Will McLean Music Festival 2027
🎶🌴 Join Us for the Will McLean Music Festival! 🌴🎶 March 12-14, 2027 📍 Florida Sand Music Ranch • Brooksville, Florida Come celebrate Florida’s rich musical heritage at the belov...
Explore eventMultiple Dates | Tom Varn Park
Art in the Park
Join the Arts Council & Pinot's Palette in Tom Varn Park for Hernando County's largest Art Show! Art in the Park is an annual event dedicated to fine art, craftsmanship, and com...
Explore eventMar 18 @ 9:00 AM - Mar 21 @ 6:00 PM EDT | 2248 Culbreath Rd, Brooksville, FL 34602, USA
Deafstock Art & Music Festival
🎉 Deafstock Music & Art Festival 2027 🎶 March 18–21, 2027 • Farm of Dreams Resort • Brooksville, FL Get ready for four unforgettable days at the beautiful Farm of Dreams Resort!...
Explore eventMultiple Dates | Stage West Playhouse
West Side Story
A musical adaptation of Romeo and Juliet set in 1950s New York City, following two young lovers caught between rival street gangs. The production is presented by Stage West Play...
Explore eventApr 17 @ 10:00 AM - 3:00 PM EDT | WellCome OM Integral Healing & Education Center
WellCome OM's 8th Annual Earth Day Celebration
An Earth Day celebration with local eco-friendly vendors and artisans, educational speakers, live demonstrations, indoor and outdoor family activities, and community wellness an...
Explore eventMultiple Dates | Stage West Playhouse
Rumors
A Neil Simon comedy in which a dinner party goes hilariously wrong as guests try to conceal a mysterious accident, producing escalating misunderstandings and farcical complicati...
Explore eventJun 19 @ 7:00 PM - 9:00 PM EDT | Stage West Playhouse
The Orlando Rat Pack
A tribute concert recreating the music, style, humor, and camaraderie of Frank Sinatra, Dean Martin, and Sammy Davis Jr., featuring classic songs associated with the Las Vegas R...
Explore eventJul 31 @ 7:00 PM - 9:00 PM EDT | Stage West Playhouse
Nearly Diamond
A Neil Diamond tribute concert starring Jonathan Elgart, featuring songs including “Cherry, Cherry,” “Cracklin’ Rosie,” and “Sweet Caroline.”
Explore eventSep 18 @ 7:00 PM - 9:00 PM EDT | Stage West Playhouse
Liverpool Live
A Beatles tribute concert featuring live musicians, authentic costumes, vintage instruments, audience participation, and songs spanning the group’s career.
Explore event
If JavaScript is disabled, this listing remains readable in the raw HTML.