Things To Do in Brooksville

A nightly walk-through glowing-pumpkin trail.

The sweeping Broadway musical about a young woman searching for her past runs three weekends at Live Oak Theatre.

A two-day family-friendly night market at Tom Varn Park with Asian food, craft and maker vendors, and cultural entertainment.

A week of activities celebrating the city's founding and heritage.

A one-hour guided evening walking tour of Brooksville's real local history and haunts, starting at the historic courthouse (6:30 PM, ages 17+, limited to 15 per tour).

A free Thursday-night blues show opening the Camping with the Blues festival weekend at Florida Sand Music Ranch.

A bayou-themed haunted house at Florida's 'most haunted' historic home.

Three days of 'Blues Under the Stars' with optional camping.

A professional Bon Jovi tribute band plays the greatest hits at Sparacia-Witherell Family Winery, 7 PM.

Brooksville's autumn pumpkin-patch tradition returns to Tom Varn Park (Oct 16–31) with pumpkins of every size, seasonal photos and fall festivities; closed Mondays.

An evening open-air harvest-themed market with artisan vendors and food in downtown Brooksville.

A Bavarian-themed market with a community chili competition.

A Rolling Stones tribute concert at Sparacia-Witherell Family Winery & Brewery.

A family farm-market day with mini cows, hands-on animal experiences and vendor stalls, 10 AM–3 PM.

A pet-friendly vendor and bargain market at the Airport Farmers & Flea Market.

A family Halloween trunk-or-treat with costumes, candy and treats at Haggard Coffee.

A multi-day live-music and camping festival at Florida Sand Music Ranch.

A high-energy Metallica tribute concert at Sparacia-Witherell Family Winery, 6–10 PM.

Downtown trick-or-treating with first responders, costume contests, and a Touch-A-Truck.

The fall edition of the gun and knife show.

A community 5K at Tom Varn Park, 8:30 AM.

A Huey Lewis and the News tribute act plays a ticketed evening show at Sparacia-Witherell Family Winery & Brewery.

A first-annual ghost-hunting-themed evening crawl through historic downtown Brooksville.

A community Halloween dance (7–9 PM) with live music from Paisley Craze and a costume contest with prizes for men's, women's and best-couple categories.

A downtown Halloween costume party at The Artist's Realm with art, music and spooky fun, 6–11 PM.

A family fall festival with games, food and seasonal activities beginning at 4 PM.

A third-annual Halloween costume stroll along historic South Brooksville Avenue with trick-or-treating and festivities.

A Pink Floyd tribute concert at the winery's intimate Peacock Theater.

Creed and Collective Soul tributes.

A family-friendly Halloween trick-or-treat stroll with candy stops and festive fun.

Classic rock 'n' roll cover band Moonshine Abby plays a free live set at Marker 48 Brewing.

A free outdoor Halloween-themed family movie night screening 'Ghostbusters' at Tom Varn Park; bring chairs and blankets.

A Halloween-themed Floor It Friday at the automotive theme park with drag racing, burnouts and a car-truck-bike meet, 5:30–10 PM.

A monthly last-Friday downtown evening of shopping, sips and socializing with local merchants.

A first-responder benefit 5K plus a family fun run.

A Halloween-night concert (7–10 PM) by Florida singer-songwriter Grant Peeples at the winery's intimate Peacock Theater.

A trail-running race through the Croom trail system.

A German-style beer festival at the flagship brewery.

A family-friendly, nature-themed Halloween event on the conservation grounds.

A Halloween dachshund costume race at the flea market.

Halloween trick-or-treating through the vendor booths.

A church fall festival with trunk-or-treating for families.

A chicken cook-off with live music, benefiting the education foundation.

A large curated vintage and craft market.

A first-Sunday automotive swap meet and vendor market for car lovers — classic cars, parts, tools and collectibles — at Florida Classic Park.

EBA-sanctioned bulls, broncs & barrels — a full rodeo.

A multi-day jam-band music and camping festival presented by Fox Fam Jam at Florida Sand Music Ranch.

Singer-guitarist Rich Sheldon returns for a free solo acoustic set (6 PM) at Broad Street Brewing Co. in downtown Brooksville.

Rock and country cover band Borderline plays a free live set at Marker 48 Brewing.

An anime-themed car convention plus drifting in the arena.

Legendary Las Vegas magician Lance Burton headlines a night of illusions, comedy and variety at Whitehead Farms, 5–10 PM.

A monthly first-Saturday oyster roast with live music at the downtown taproom and bourbon bar.

The national T2T charity 5K honoring first responders and military.

A Mediterranean dinner-and-concert evening at the Olive Grove featuring surf-rockabilly band Igor & the Red Elvises, starting 5 PM.

A multi-day music festival.

Live Oak's youth performers stage the beloved family musical about orphan Annie over two weekends.

The free downtown concert series returns with The Gaturz, plus an artisan market, food trucks, and a full bar, 6:30–9:30 PM.

A blues-and-soul concert from Michael Allman (son of Gregg Allman), presented by WRP at the winery, 7–10 PM.

A canine disc and dog-sport competition weekend with high-flying frisbee dogs at Florida Classic Park.

Award-winning Florida blues guitarist Selwyn Birchwood brings his electric blues band to the winery.

A multi-day live-music and camping festival at Florida Sand Music Ranch.

A trail 'adventure run' with a costume turkey-trot option.

A Thanksgiving-season street market with artisan vendors and food trucks at the historic water tower.

The fall edition of the quarterly model-train exhibition and marketplace (9 AM–2 PM) with 70+ vendor tables and operating layouts.

A Toby Keith country tribute with food trucks at the hilltop vineyard, 6–10 PM.

A Thanksgiving-morning 5K benefiting Shop With a Cop.

A downtown shopping event supporting local merchants.

A Led Zeppelin tribute on Thanksgiving weekend.

A classic car show with vendors, crafts, and food booths.

A Thanksgiving-weekend bluegrass festival at the ranch.

A military-appreciation vendor market downtown.

A tribute to The Police and Sting on the winery's outdoor concert stage, 6–10 PM.

The signature holiday kickoff — live performances, a craft market, Santa photos, and the tree lighting.

A first-Sunday automotive swap meet and vendor market for car lovers — classic cars, parts, tools and collectibles — at Florida Classic Park.

Live Oak Theatre's youth troupe stages a family adaptation of C.S. Lewis's Narnia classic.

A family holiday-season stage adaptation of the Narnia tale, part of Live Oak's 2026-27 youth season.

A Victorian-themed holiday evening at the historic May-Stringer House with period decor and festive cheer.

A Simon & Garfunkel tribute concert with wine and food trucks at the vineyard, 6–9:45 PM.

A 50-plus-year tradition with marching bands and floats.

A Queen tribute concert at Sparacia-Witherell Family Winery, 6 PM.

An intimate live-music evening with Peg & Em at the winery's cozy Peacock Theater, 7:30–9:45 PM.

A sensory-friendly holiday event with adaptive lighting, quiet zones, and Santa.

A holiday-themed drift festival.

A festive holiday neighborhood stroll.

A free outdoor holiday family movie night screening 'The Polar Express' at Tom Varn Park; bring chairs and blankets.

A year-end holiday drag-racing festival with Santa Claus, live concert and a vehicle showcase at the automotive theme park.

A diecast Hot Wheels collectible show with vendor tables, trading, and displays for collectors and families at American Legion Andrew Jackson Post 99.

Brooksville's New Year's Eve street party with a midnight glowing-tangerine drop.

Santa photos, cookie decorating, and a light trail.

A long-distance road-cycling ride through Hernando's hills.

An annual citizen-science bird census with Hernando Audubon.

Endurance and ultra trail races through Florida oak-hammock forest.

Ten-plus days of AKC all-breed conformation dog shows.

Singer Michelle Ingrham performs a live set at the intimate Peacock Theater at Sparacia-Witherell Family Winery, 7:30–9:30 PM.

The world's largest hammock-camping gathering — workshops, gear demos, music and community campouts at Florida Sand Music Ranch.

A birthday celebration and drag-racing event honoring 'Big Daddy' Don Garlits at Lead Foot City.

A community parade honoring Dr. Martin Luther King Jr.

The winter edition of the quarterly model-train show and sale (9 AM–2 PM) with vendors and running layouts.

A literary festival with authors, readings, and family activities.

A gun and knife show with dealers and vendors (recurs several times a year).

A large Civil War re-enactment by the Hernando de Soto Historical Society.

A skill-bracket pickleball tournament.

35- and 50-mile mountain-bike rides on the Croom trail system, plus camping.

An Americana roots-music festival weekend.

A three-day swap meet and car show at Florida Classic Park with classic cars, automotive vendors and collectibles.

A citrus-themed street festival with classic cars, artists, food, and small-town charm.

A truck show at Florida Classic Park.

A Rush tribute concert at the hilltop muscadine winery, 7 PM.

A family- and dog-friendly five-day camping festival of funk, jam and live electronic music at Florida Sand Music Ranch.

Intertribal dancing, drumming, Native crafts, food, and cultural demonstrations.

Celtic and Scottish-Irish music, Highland demos, competitions, and vendors.

A home-improvement, remodeling, and garden vendor expo (Chamber of Commerce).

The Disc Golf Pro Tour comes to town — the county's biggest disc-golf event.

The Alzheimer's Association awareness and fundraising walk.

The beloved Florida folk festival honoring the 'Father of Florida Folk' — three days of songwriters and campground picking.

The free downtown concert series in spring swing.

The Fine Arts Council's flagship festival — 100+ artists, live music, and a student art show.

A two-day Chevy/GMC C10 and classic-truck show presented by LMC Truck with camping, vendors and awards at Florida Classic Park.

A four-day music, art, and community festival.

A free Thursday-night kickoff concert ahead of the 8th annual Blues Bash at the Ranch.

A multi-day blues festival with camping at the music ranch.

A youth-theatre stage adaptation of Tolkien's classic adventure, part of Live Oak's expanded 2026-27 season.

A spring-migration festival with guided bird walks, talks, and kids' activities.

A sighthound lure-coursing trial weekend at Florida Classic Park.

A weekend hot air balloon festival at Florida Classic Park with balloon launches, family activities and vendors.

A Pink Floyd tribute concert at the hilltop muscadine winery, 7 PM.

30+ prizes, a kid zone, vendors, and raffles benefiting Rotary charities.

A regional farming, wildlife, and natural-resources showcase.

A multi-bracket pickleball tournament.

The Lerner & Loewe musical comes to the Live Oak mainstage across three weekends in April.

Free downtown concert with a market, food trucks, and full bar.

A free pre-festival reunion night of live music ahead of the 9th annual Rock & Roll Revival.

A camping-optional festival celebrating 1960s–70s rock on 80+ acres.

An environmental-awareness Earth Day event.

A country music and camping festival returning for its second year at Florida Sand Music Ranch.

The spring edition of the International All Breed Canine Association dog show at Florida Classic Park.

A trail ultramarathon with 50-mile, 50K, and 16-mile options.

The county's largest annual event — carnival rides, youth livestock shows, exhibits, and concerts.

A family bike-riding day with safety demos and wellness stations.

A two-division charity cornhole tournament.

A walk supporting survivors of domestic and sexual violence.

Live Oak's youth performers stage the classic rock-and-roll musical comedy over two weekends.

A multi-day festival celebrating the local blueberry harvest — vendors, music, food, and a kids' zone.

A multi-day jam-band music and camping festival.

The spring edition of the quarterly model-train show and sale (9 AM–2 PM) with vendors and operating layouts.

A youth-theatre staging of the Frances Hodgson Burnett story closes out Live Oak's 2026-27 season.

Memorial-themed races benefiting The Arc Nature Coast.

A celebration of African American heritage with historians, readings, and line dancing.

A timed cross-country mountain-bike race in the Florida Endurance Series.

A community Juneteenth observance with music and vendors.

An evening moonlight trail run with 21-, 14-, and 7-mile options.

A free outdoor screening of a classic film with a DJ beforehand.

The free summer reading program launches with family activities and prizes.

An annual Fourth of July demolition derby capped with a fireworks show at the county fairgrounds.

The fall edition of the quarterly model-train show and sale (9 AM–2 PM) with vendors and operating layouts.

The late-fall edition of the quarterly model-train show and sale (9 AM–2 PM) with vendors and operating layouts.

Seniors (55+/AARP), active and retired military, and first responders: always ask — many local spots discount even when it isn't advertised.

A restored 1885 railroad depot and a replica one-room schoolhouse; one ticket covers both, with a docent tour. Fri & Sat noon–3.

A City of Brooksville senior program (55+) — aerobics, resistance-band training and fun athletic games at the Jerome Brown Community Center.

A large flea and produce market, rain or shine.

Weekend live music and Sunday karaoke at the market's Center Stage tiki bar.

A salvage and vintage shop known regionally for its impressive vinyl-record collection.

Recurring bingo and a Friday fish fry; call for game nights.

Family fall festivals and u-pick pumpkin fields in October.

An upscale 55+ RV resort — full-hookup concrete sites, heated pool, hot tub, fitness center and pickleball.

Polished-casual wood-grilled seafood with a strong wine & martini bar — home of the famous Bang Bang Shrimp. A reliable date-night option.

A classic old-Florida roadside stop since the 1960s — a small wildlife park, a 'dinosaur cave,' mini-golf, gold panning, and ice cream.

A downtown Brooksville brewery with weekend live music.

A weekly Saturday farmers market with local produce, fresh-cut meats, and craft vendors at Central Florida Beef.

Vinyasa, Yin, Hot Yoga, 26&2, chair yoga, restorative, meditation and sound baths in downtown Brooksville.

A nationally ranked destination golf resort; Citrus/Hernando residents get discounted rates.

Discounted golf rates for Citrus/Hernando residents (with ID) at the nationally ranked resort.

A gated RV park with 66 paved sites, a geothermal heated pool, Sparkman Lake fishing, shuffleboard and a rec hall.

A nature center with trails, guided walks, wildlife programs, and a monthly 3D archery shoot (first Saturdays). The center and its Lake Lindsey Rd lot are open Fri & Sat (plus scheduled programs); other trailheads are open daily, dawn to dusk.

An 1850s antebellum manor on one of the county's highest hilltops; weekend tours (confirm seasonal schedule).

An urban-style steakhouse & grill — steak au poivre, ribeye, lamb chops and mahi mahi in a casual-but-elevated setting.

Famous footlong chili dogs since 1960, with walls of Hernando County history.

A festival-style market of local farmers, artisans, bakers, and food trucks (themed each month).

The popular drive-thru coffee chain is expanding into Brooksville (confirm opening).

A 113-acre youth sports park with baseball/softball and soccer fields, basketball courts, a playground, picnic shelters and grills.

A large 24/7 fitness club coming to the Brookridge Central / SR-50 area in 2026.

A genuinely under-visited 2.3-mile loop through three distinct ecosystems (dogs welcome).

Gymnastics and tumbling for ages 1 through teens, boys-only tumbling & trampoline, and tricks/martial-arts tumbling.

A weekly drag-strip test-and-tune and car night.

The county's signature destination restaurant — shrimp & grits, chicken & waffles, and an epic wall of bourbon.

A downtown taproom and bourbon bar with occasional acoustic live music.

A large outdoor concert and camping venue hosting jam-band and country festivals.

County preserves, trails, and boat ramps plus all Hernando County Library programs are free (some parks charge parking).

Free live music downtown with an artisan market, food trucks, and a full bar.

Artistic gymnastics, trampoline & tumbling, boys gymnastics, aerial silks/circus arts and adult classes — toddlers to teens. Step Up For Students accepted.

Tumbling for all ages, recreational and All-Star competitive cheer, private lessons and summer camp. USASF member gym.

The City-sponsored gallery inside City Hall — about four themed exhibits a year, each with an opening reception.

A paved rail-trail running east from the historic 1885 depot — a great family bike ride.

Part antique store, part community hub — vintage furniture and décor plus a community garden and workshops.

The county's multiplex — 2D, 3D and GTX large-format screens. Bargain Tuesdays are the best deal in town.

A café pairing coffee with curiosities and collectibles — hosting bike nights and vendor markets. Opened Jan 2026.

A value-focused RV park with clean sites, showers and a community garden, minutes from Weeki Wachee Springs.

Free guided birding walks across the county's preserves and parks (roughly monthly, fall–spring).

Covers paid-parking county parks for 12 months — pays for itself fast if you use the beaches, boat ramps, and parks often.

Storytimes, book clubs, computer classes, and more at the county library branches — check the calendar for current branch hours.

Southern Hills Plantation, Brooksville G&CC, Silverthorn, Sherman Hills, Timber Pines (55+), and Quarry Golf.

Low-cost community bingo at the senior center.

A free self-guided tour of a walkable historic district — architecture, murals, boutiques, and antiques.

Hot Power, Warm Vinyasa Flow, Stretch & Tone, unheated and Yin yoga — plus a free monthly outdoor community yoga class.

Hatha, Yin and Chair yoga for all levels — beginners always welcome. One of the most affordable studios in the county.

Children's dance instruction in a welcoming, beginner-friendly studio.

Ballroom, Latin and social dance for adults — Foxtrot, Tango, Waltz, Cha Cha, Rumba, Salsa, Swing and Hustle.

A bright, popular breakfast-and-brunch cafe for pancakes, omelets, and fresh-fruit crepes.

375 acres with horseback riding trails, a fishing pier, a Withlacoochee River boat ramp, and cycling paths in the eastern part of the county.

Knights of Columbus fish-fry dinners at St. Anthony the Abbot and St. Frances Cabrini.

Brooksville's community theater, with a full season of mainstage and youth productions.

The county's genuinely hidden eats move around — locals follow the trucks via StreetFoodFinder and the area food-truck Facebook group.

The county's flagship craft brewery with a big beer garden, live music, food, and events.

The flagship brewery's beer garden hosts live music and food trucks on select weekends.

UF/IFAS Master Gardener plant sales and monthly Florida Native Plant Society programs.

Evening paranormal tours and late-night investigations of the historic museum (ages 16+, reservations).

A Queen Anne Victorian mansion — often called Florida's most haunted house. Tue–Sat 11–3.

The veteran and first-responder-themed BBQ chain drew big crowds on Cortez Blvd. Opened early 2026.

Free outdoor family movie nights at the bandshell.

Volunteer-run themed gardens with butterfly and rose beds, ponds, and a gazebo. Open daily dawn–dusk.

The long-awaited Italian-American restaurant landed on Brooksville's 'restaurant row.' Opened May 2025.

Free drop-in open-court basketball and pickleball at the Jerome Brown Community Center — plus a first-responder open-court night on Wednesdays.

A long-standing white-tablecloth date-night spot — upscale Italian with prime steaks and seafood. Try the Shrimp Joe or Zuppa di Pesce.

Scheduled social painting classes with a new guided canvas each session.

An independent fine-dining steakhouse with premium hand-cut steaks, fresh seafood and lobster tail in an upscale, wine-focused room.

A winery with a heavy tribute-band calendar plus reggae, blues, and food-truck nights.

Wine tastings at the hilltop muscadine winery (Wed–Sun); most weekends bring tribute-band concerts and food trucks.

A monthly classic car show and automotive swap meet.

Free family open gym with games and crafts, plus a monthly toddler sensory playdate, at the Jerome Brown Community Center.

A new community art and creative studio. Opened Feb 2026.

An eclectic American bistro in historic downtown — wood-fired pizzas, handmade pasta, swordfish with lobster glace and surf & turf.

A rustic music farm with a weekly Thursday jam and singer-songwriter listening-room shows.

A casual downtown sandwich-and-lunch spot popular with the courthouse-square crowd.

A City of Brooksville park with a paved trail around a pond (a National Recreation Trail), a splash pad, playground, ball diamond, volleyball and pavilions.

Seasonal u-pick blueberry and berry farms in spring (~April–May).

A new trade school offering cybersecurity, automotive, cosmetology, law enforcement, and more. Opened Apr 2025.

157,000 acres for hiking, mountain biking, horseback riding, camping, and off-road riding at the Croom Motorcycle Area.