• Nov 28 @ 7:00 PM - 11:00 PM EST | Brian's Place

  Justin Phillips

  Find tickets for Justin Phillips at Brian's Place in Spring Hill on 8/29/2026 at 7:00 PM. 

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• Nov 29 @ 1:00 PM - 3:00 PM EST | 12560 Spring Hill Dr, Spring Hill, FL 34609

  DIY Christmas Ornaments

  Christmas Art & Craft Therapy Social ✨ Unwind and connect with us for a deeply therapeutic afternoon of creativity and wellness!

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• Dec 4 @ 9:30 AM - 12:30 PM EST | 28207 Old Trilby Rd, Brooksville, FL 34602, USA

  Lattes & Littles On The Farm

  Join us for Lattes & Littles on the Farm on Friday, December 4 from 9:30am-12:30pm for a cozy, fun-filled morning designed just for parents and their little ones! Enjoy...

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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 4 @ 6:00 PM - 10:00 PM EST | Weeki Wachee Springs State Park

  Winter Waterland – Lights Only Preview

  Get an early look at the holiday magic during the Winter Waterland Lights Only Preview at Weeki Wachee Springs State Park. Take a festive stroll through the park and enjoy holid...

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• Dec 4 @ 6:30 PM EST | 309 S Main St, Brooksville, FL 34601, USA

  Gingerbread House Party

  Join us for a fun filled night of creating gingerbread houses. All supplies included to make your masterpiece! $25

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• Dec 5 @ 9:00 AM - 12:00 PM EST | Bishop McLaughlin Catholic High School

  Jingle Bell Dash 5K Run/Walk

  Festive 5K run/walk on a cross-country course throughout Bishop McLaughlin Catholic High School’s 88-acre campus. Proceeds benefit the school’s Athletic Department and Track & F...

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• Dec 5 @ 11:00 AM - 4:00 PM EST | Strong Tower Vineyard & Winery

  Christmas Sip & Shop

  A holiday shopping event at Strong Tower Winery featuring local vendors, wine, holiday sips, music by DJ Deezy, The Real Deal Food Truck, a coffee bar, a mobile bookshop, and ot...

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• Dec 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,...

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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 @ 2:00 PM EST | Spring Hill United Church of Christ

  Weeki Wachee Winds Holiday Concert

  Holiday concert by the Weeki Wachee Winds community concert band.

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• Dec 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...

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• Dec 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,...

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• Dec 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!

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• Dec 5 @ 8:30 PM EST | Uptown Bar & Grill

  BORDERLINE @ Uptown Bar & Grill

  BORDERLINE @ Uptown Bar & Grill

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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 @ 10:30 AM - 1:30 PM EST | VFW Post 8681

  DIECASTARAMA • DECEMBER 6, 2026

  Family-friendly diecast-model show featuring vendors, new releases, classic models, Hot Wheels customs, and opportunities to learn about making custom cars.

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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 9 @ 2:00 PM - 3:00 PM EST | Spring Hill Branch Library

  Owls of Hernando County @ Spring Hill Branch

  Program about local owl species, their adaptations and behaviors, their roles in Florida ecosystems, and ways to help protect owls and their habitats. Presented in partnership w...

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• Dec 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...

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• Dec 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...

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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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• Multiple Dates | Weeki Wachee Springs State Park

  Winter Waterland 2026

  Celebrate Winter Waterland at Weeki Wachee Springs, Dec. 11-12 & 18-19, with holiday shows, Santa, festive lights and family fun!

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• Multiple Dates | 6131 Commercial Way, Spring Hill, FL, 6131 Commercial Way, Spring Hill, FL 34606-1121, United States

  Breakfast with Santa at Weeki Wachee Springs

  Celebrate the season with a festive morning at Breakfast with Santa at Weeki Wachee Springs State Park! Enjoy a buffet-style breakfast while Santa stops by for story time, photo...

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• Dec 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...

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• Dec 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.

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• Dec 12 @ 10:00 AM EST | Downtown Brooksville

  52nd Annual Brooksville Christmas Parade

  Annual Brooksville Christmas Parade presented by the Kiwanis Club of Brooksville. The 2026 theme is “250 Years of Christmas in America.”

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• Dec 12 @ 6:00 PM EST | 7244 Shoal Line Blvd, Spring Hill, FL 34607, USA

  Weeki Wachee Christmas Boat Parade

  Watch the festive Christmas Boat Parade starting at 6pm in front of Rogers Park in Weeki Wachee! Featuring live music by Tre Dicci. Sponsored by The Kayak Shack. No cost to...

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• Dec 13 @ 10:00 AM - 3:00 PM EST | Staples Spring Hill

  Staples Christmas Car Show

  A public Christmas car show featuring judged and non-judged vehicle entries, DJ music, vendors, food trucks, raffles, and trophies across multiple categories. Non-judged entry i...

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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 EST | Stage West Playhouse

  Candy Cane Chaos #2

  High-spirited youth holiday show presented by Stage West Playhouse, featuring festive comedy, seasonal fun, and family-friendly entertainment.

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• Dec 17 @ 5:30 PM - 7:00 PM EST | Spring Hill Branch

  Star Party: Astromony Experience @ Spring Hill Branch

  Explore the wonders of the night sky at the Spring Hill Library. This telescope viewing party offers a chance to observe the Moon, stars, and other celestial objects through a t...

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• Dec 18 @ 12:00 AM - Dec 20 @ 12:00 AM EST | Stage West Playhouse

  Candy Cane Chaos #2

  A family-friendly youth holiday show featuring festive comedy, seasonal cheer, and a high-spirited North Pole adventure. Performances are scheduled for December 18–20, 2026.

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• Dec 18 @ 10:30 AM - 11:30 AM EST | Main Library

  Holiday Edition Walk & Talk for Adults @ Main Library

  A one-mile guided walk and talk about local history and Brooksville’s historic buildings, with Christmas decorations along the route. The walk begins and ends at the Main Librar...

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• Dec 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...

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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 | WellCome OM

  The Once Upon an OM Winter Faire

  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, farm...

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• Dec 19 @ 10:00 AM EST | Brooksville Cemetery

  Wreaths Across America

  Wreaths Across America at Brooksville Cemetery REMEMBER the Fallen. HONOR those who Serve. TEACH our children the value of Freedom. Join us at Brooksville Cemetery on Saturday,...

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• Dec 19 @ 4:00 PM EST | Tom Varn Park

  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 23 @ 1:00 PM - 3:00 PM EST | Spring Hill Branch

  Holiday Movie Matinee for Families @ Spring Hill Branch

  Join us for a special holiday movie matinee. Popcorn will be served. The event is for children and their caregivers. Rated PG, with a 105-minute runtime. Registration is required.

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• Dec 31 @ 8:00 AM - 11:00 AM EST | Weeki Wachi preserve

  New Year’s Eve 5.5k!

  A New Year’s Eve 5.5-kilometer race at Weeki Wachi Preserve. All ages and fitness levels are welcome; the event celebrates Jose turning 55 and encourages participants to end 202...

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• Dec 31 @ 7:00 PM - 1:00 AM EST | Brooksville Water Tower

  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 | 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.

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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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• Multiple 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...

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• Jan 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...

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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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• Jan 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...

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• Jan 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...

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• Jan 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...

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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 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...

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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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• Multiple 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...

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• Feb 20 @ 7:00 AM EST | 309 S Main St, Brooksville, FL 34601, USA

  Books, Brews and Brushstrokes

  CALLING ALL VENDORS, DRINK CREATORS & ARTISTS! We’re gearing up for a day full of books, brews, creativity, and community, and we want YOU to be part of it! BOOKIS...

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• Feb 27 @ 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, February 27th, 2027, one of the most celebrated magicians in the world will...

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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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• Multiple 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...

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• Multiple Dates | 85 Myers Rd, Brooksville, FL 34602, USA

  ROCK & ROLL REVIVAL

  Join us at the Florida Sand Music Ranch for the 9th annual Rock & Roll Revival - 60's/70's music festival! Three days of peace, love & music, with a fantastic & dive...

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• Apr 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...

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• Multiple 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...

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• Multiple Dates | 5 Myers Rd, Brooksville, FL 34602, USA

  GONE COUNTRY AT THE RANCH

  You do not want to miss these incredible country music bands! Saddle up, Florida, and head out to Florida Sand Music Ranch, Brooksville, FL! We're not messing around! Book now t...

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• Jun 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...

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• Jul 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.”

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• Sep 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.

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