• Nov 6 @ 12:00 PM - Nov 8 @ 11:45 PM EST | 85 Myers Rd, Brooksville, FL 34602, USA

  Fox Fam Jam Presents: Phantasmagoria

  FOX FAM JAM Presents:  🎃🦊PHANTASMAGORIA 🦊🎃  Victorian spooky themed Everything!!  This one is going to be fancy!! 🦊🦊Fancy Fall Fox Ball!! 🦊🦊  We are so excit...

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• Nov 6 @ 6:30 PM EST | Marker 48 Brewing

  BORDERLINE @ Marker 48

  BORDERLINE @ Marker 48

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• Nov 7 @ 2:00 PM - 8:00 PM EST | 14311 Spring Hill Dr, Spring Hill, FL 34609, USA

  Art & Ales: Round 2

  Join us for an immersive live art event, Art & Ales! Watch talented artists go head-to-head in a 6-hour live painting challenge, each creating a unique work of art inspired by a...

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• Nov 7 @ 2:00 PM - 10:00 PM EST | 17109 Old Ayers Rd, Brooksville, FL, United States, Florida 34604, 17109 Old Ayers Rd, Brooksville, FL 34604-6808, United States

  Tokyo Takeover of Lead Foot City - Anime Auto Con, Asian Drift Fest (Nov 7, 2026)

  Tokyo Takeover of "Send it Saturday" Drift Fest at Lead Foot City. This is a special themed event together with the Anime Auto Con. EXPERIENCE the Thrills of.. - Drifting, watch...

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• Nov 7 @ 5:00 PM EST | 7136 Cedar Ln, Brooksville, FL 34601, USA

  Lance Burton-Master Magician & Friends

  TICKETS ARE NOW LIVE!🪄🎩 LANCE BURTON & FRIENDS is coming to Whitehead Farms! On Saturday, November 7, one of the most celebrated magicians in the world will take the stage right...

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• Nov 7 @ 7:00 PM - 8:30 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

  Two Cicks and a Horse Tail: Comedy Special

  Two Chicks and a Horse Tail Get ready for a night of big laughs, bold personalities, and just the right amount of trouble at Two Chicks and a Horse Tail! Featuring three hilario...

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• Nov 8 @ 5:00 PM EST | 15016 Rester Drive, Brooksville, FL, United States, Florida 34613, 15016 Rester Dr, Brooksville, FL 34613-4305, United States

  A Night at the Olive Grove

  A Night at The Olive Grove featuring "Igor and the Red Elvises" & The Amber Lynn Nicol DuoMediterranean Dinner with the Red Elvises. November 8th, 2026Show only $20/Door $25...

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• Nov 11 @ 6:00 PM - Nov 15 @ 10:00 PM EST | 85 Myers Rd, Brooksville, FL 34602, USA

  Florida Winter Music Festival

  www.foggylongbritches.com

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• Nov 13 @ 7:00 AM - 5:00 PM EST | The Olive Grove, 15016 Rester Drive, Brooksville, FL, United States

  Pit Fire

  Stop by and purchase some clay, create something wonderful and keep creating so you have several pieces to fire on November 13th at 7am in the fire pit. We’re here Fridays, Satu...

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• Nov 13 @ 6:30 PM - 9:30 PM EST | 205 E. Fort Dade Ave., Brooksville, FL, United States, Florida 34601, 205 E Fort Dade Ave, Brooksville, FL 34601-2613, United States

  Friday Night Live- November 2026

  THE FINAL FRIDAY NIGHT LIVE OF THE YEAR IS HERE! Brooksville, are you ready to give 2026 the epic musical send-off it deserves? Pack up the family, grab your friends, and join u...

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• Nov 13 @ 7:00 PM - 10:00 PM EST | 21509 Snow Hill Road, Brooksville, FL 34601

  WRP Presents The Michael Allman Band

  Get ready to rock with WRP and The Michael Allman Band live in concert—pure blues and soul vibes!

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• Nov 14 @ 7:00 PM - 8:30 PM EST | 8390 Forest Oaks Boulevard, Spring Hill, FL 34606

  SPRING HILL COMEDY NIGHT: From Discovery Channel - Carmen Ciricillo - 11/14

  Laffs2Go Presents: Carmen Ciricillo from Discovery Channel, Drybar Comedy & SiriusXM LIVE in Spring Hill on Saturday, November14th 2026!

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• Nov 19 @ 5:30 PM - 6:30 PM EST | 20 N Main St, Brooksville, FL 34601-2800, United States, 20 N Main St, Brooksville, FL 34601-2800, United States

  Community Dedication Ceremony for the Dr. Dennis Wilfong Memorial Sleigh

  Brooksville Main Street, together with the local community, invites residents, business owners, and visitors to attend the official dedication ceremony of the Dr. Dennis Wilfong...

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• Nov 20 @ 9:00 AM - Nov 22 @ 11:00 PM EST | 85 Myers Rd, Brooksville, FL 34602, USA

  Cornucopia Music Fest 2026

  🌾 CORNUCOPIA MUSIC FEST 2026 🌾 Nov 20-22, 2026 | Florida Sand Music Ranch 386.385.3500 EvansMediaSource.com When everything starts sounding the same... it’s time for Cornucopia.

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• Nov 20 @ 12:00 PM - Dec 6 @ 12:00 PM EST | Stage West Playhouse

  The Game’s Afoot

  Stage West Playhouse presents: The Game’s Afoot\nNovember 20-22, 27-29 & December 5 & 6, 2026\nSherlock Holmes meets Noel Coward in this clever, fast-paced whodunit. When a holi...

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• Nov 20 @ 6:00 PM EST | HH3X+P2, 301 Darby Ln, Brooksville, FL 34601, USA

  Movie Night: G.O.A.T.

  Get ready to shoot, score, and soar at our November Movies in the Parks event! Join us on Friday, November 20 for a slam-dunk evening featuring the animated film G.O.A.T. Before...

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• Nov 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...

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• Multiple 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...

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• Nov 21 @ 10:00 AM - 2:00 PM EST | 101 S Brooksville Ave, Brooksville, FL 34601-3310, United States, 110 S Brooksville Ave, Brooksville, FL 34601-3309, United States

  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...

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• Nov 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.

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• Nov 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

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• Nov 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!

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• Multiple 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...

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• Nov 28 @ 10:00 AM - 2:00 PM EST | Historic Downtown Brooksville, Florida, 122 S Main St, Brooksville, FL 34601-3335, United States

  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...

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• Nov 28 @ 6:00 PM - 9:45 PM EST | 21509 Snow Hill Road, Brooksville, FL 34601

  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!

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• Dec 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.

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• Dec 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.

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• Dec 5 @ 3:00 PM - 9:00 PM EST | 20 N Main St, Brooksville, FL 34601-2800, United States, 20 N Main St, Brooksville, FL 34601-2800, United States

  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...

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• Dec 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...

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• Dec 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.

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• Dec 11 @ 6:00 PM - 9:00 PM EST | 601 Museum Ct, Brooksville, FL 34601-2631, United States, 601 Museum Ct, Brooksville, FL 34601-2631, United States

  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...

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• Dec 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.

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• Dec 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...

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• Dec 17 @ 12:00 PM - Dec 20 @ 12:00 PM EST | Stage West Playhouse

  Candy Cane Chaos #2

  Stage West Playhouse presents: Candy Cane Chaos #2\nDecember 17-20, 2026\nBack by popular demand! A high-spirited youth holiday show full of festive fun, laughter, and seasonal...

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• Dec 18 @ 5:00 PM - 9:00 PM EST | 205 E. Fort Dade Ave., Brooksville, FL, United States, Florida 34601, 205 E Fort Dade Ave, Brooksville, FL 34601-2613, United States

  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...

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• Dec 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...

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• Dec 19 @ 10:00 AM - 3:00 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

  The Once Upon an OM Winter Faire

  Hear ye, hear ye! The story begins with you... Step into a world of wonder at Once Upon an OM Winter Faire! Join us for a magical celebration where fairytales, fantasy, and Rena...

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• Dec 19 @ 2:00 PM - 9:00 PM EST | 17109 Old Ayers Rd, Brooksville, FL, United States, Florida 34604, 17109 Old Ayers Rd, Brooksville, FL 34604-6808, United States

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

  CALL 844-532-3366 FOR ANY QUESTIONSMerry Driftmas Holiday Drift Fest at Lead Foot City. This is an open drift event that will have different themes and layouts throughout the ye...

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• Dec 19 @ 4:00 PM EST | Tom Varn Park, 301 Darby Ln, Brooksville, FL 34601-3178, United States

  Movie Night- Polar Express

  All Aboard the Polar Express Movie Night! All aboard! The conductor is calling, and the train is preparing to depart from Tom Varn Park for a magical evening filled with Christm...

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• Dec 31 @ 7:00 PM - 1:00 AM EST | 101 S Brooksville Ave, Brooksville, FL 34601-3310, United States, 110 S Brooksville Ave, Brooksville, FL 34601-3309, United States

  NYE Tangerine Ball Drop 2026

  MAIN STREET IS GLOWING: THE TANGERINE BALL DROP 2027! Brooksville, are you ready to squeeze every last drop of fun out of 2026? We’re throwing the ultimate New Year’s Eve street...

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• Jan 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...

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• Jan 9 @ 12:00 PM - 5:00 PM EST | 1300 Mariner Boulevard, Spring Hill, FL 34609

  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.

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• Multiple 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...

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• Jan 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.

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• Jan 15 @ 12:00 PM - Jan 24 @ 12:00 PM EST | Stage West Playhouse

  She Loves Me

  Stage West Playhouse presents: She Loves Me\nJanuary 15-17 & January 22-24, 2027\nA tender, romantic musical with lush melodies and timeless charm. Two shop clerks can’t stand e...

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• Jan 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...

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• Jan 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.

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• Feb 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

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• Feb 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...

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• Feb 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

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• Feb 19 @ 12:00 PM - Mar 7 @ 12:00 PM EST | Stage West Playhouse

  Social Security

  Stage West Playhouse presents: Social Security\nFebruary 19-21, 26-28 & March 6 & 7, 2027\nA smart, laugh-out-loud comedy about family, aging parents, and the well-meaning chaos...

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• Multiple 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...

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• Mar 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...

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• Mar 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...

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• Multiple 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...

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• Mar 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!...

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• Apr 17 @ 10:00 AM - 3:00 PM EDT | 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

  WellCome OM's 8th Annual Earth Day Celebration

  SAVE THE DATE: Earth Day 2027! Mark your calendars! The WellCome OM Center is thrilled to announce our 8th Annual Earth Day Celebration is happening on Saturday, April 17th, 202...

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• Apr 22 @ 12:00 PM - May 9 @ 12:00 PM EDT | Stage West Playhouse

  Rumors

  Stage West Playhouse presents: Rumors by Niel Simon\nApril 22-25, 30 & May 1-2 & 8-9, 2027\nNeil Simon at his absolute funniest. A dinner party goes hilariously off the rails as...

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