Brooksville Main Street is a vibrant Main Street program bringing a passion for celebrating Christmas for a whole month!

It’s like someone said, “let’s make downtown Brooksville just like a Hallmark^® movie!”

Oversized Christmas trees with synchronized holiday music, Santa, sleighs, packages, candy canes, local musicians, dancers, churches, horse drawn carriage sleigh rides, snow, and a LOT of community involvement make Brooksville truly a worthwhile destination for celebrating Christmas.

In 2016 Barbara Manuel, Chair of the newly formed Promotions Committee, visited Wiregrass Mall in Wesley Chapel for their “Symphony in Lights.” Barbara noticed how many people were visiting from near and far and envisioned a way to make Brooksville a destination, so she spearheaded the Brooksville Main Street Christmas.

Fundraising to purchase a musical tree with synchronized lights over 35 feet tall was one of Main Street’s first projects. “We became an official Main Street in 2016. At that time, the City was putting up smaller trees. We wanted to really make Brooksville shine while providing holiday magic to families without any cost to those families,” Barbara explained.

Private and public donations funded the tree, and most everything else that goes into making historic downtown Brooksville shine during the “most wonderful time of the year” … year after year organized and managed by the Main Street team.

Brooksville Main Street has only two paid staff members and over 300 volunteers on their roster. That may be part of what adds to the magic.

The amazing tree still plays holiday songs with synchronized lights throughout the month of December providing just the right touch of Main Street Christmas cheer as you stroll the downtown.

Brooksville Main Street provided an additional tree for the front of City Hall a few years later, which twinkles with holiday magic while playing music throughout the season.

Raising the 35-foot Christmas tree in front of the historic Hernando County Courthouse is a big project each year. NatureCoaster caught up with Natalie Kahler, Barbara Manuel, and Barry DeBarr as they were working on the tree and decor to get details on this year’s festivities.

“The trees start each evening at 6 pm, playing different music and setting the holiday mood,” explains Natalie Kahler, Executive Director for the Main Street program, as she is helping to erect the decorations, working out event details, and taking phone calls.

Catch the Official Christmas on Main Tree Lighting Celebration Dec. 1

The official lighting ceremony is December 1 this year. (It is always the first Thursday evening in December) Brooksville’s streets are closed from City Hall (Fort Dade) to Hendricks Street and from the historic May Stringer House (Jefferson) to Lemon Street. 100 vendors will be offering artisan crafts and food for sale from 4-9pm.

Park in one of the city lots or along the adjoining streets and enjoy a leisurely walk to the historic Hernando County Courthouse to participate in this celebration kicking off the holidays!

The Brooksville community gets involved in a big way.

The Live Oak Theatre, a local performing arts group provides and schedules live entertainment through the event. The tree is lit at 6:45 pm and Santa Claus is on hand at Mulligan Law Firm for free photos!

The Brooksville Woman’s Club, across the street from Santa, will be holding an open house and, at 7:45 pm, Patricia’s Windows Come to Life at Patricia’s Boutique with local teens donning beautiful gowns and creating a live display, dancing in the floor to ceiling windows along Broad Street to the tunes of a local DJ.

Across the street from Patricia’s, the Hogan Law firm will be hosting free kids holiday craft in their garage – and everyone is welcome!

Brooksville Main Street Celebrates Christmas throughout December

After the fun of Christmas on Main Street’s Tree Lighting event, there is still a long lineup of community events and activities to make it worth returning week after week.

From December 2 to December 31, both giant Christmas trees light up with holiday music each evening at 6.

On Friday and Saturday, live music by local churches or musical groups is held on the Courthouse steps for about 45 minutes, bringing the community together. The streets are open, and it is relaxing to stop by and enjoy the sounds of the Main Street Christmas.

Each year, Brooksville Main Street has worked to add to its Christmas on Main Street décor and events. Snow was added to the tree lighting, a Christmas-theme window decorating contest is held for the downtown businesses, Christmas characters were added, including reindeer on the awnings of the buildings across from the Courthouse.

This year, a 12-foot Christmas ornament with an open window has been erected on the Courthouse lawn, providing another wonderful photo op. Inside is a life-sized sleigh, added in 2021 in honor of Denis Wilfong, a long-time Brooksville and Main Street supporter, for visitors to enjoy photo ops in and with.

Schedule your Christmas Carriage Ride

Carriage Rides are held on December 14, 15, 21, and 22 this year. There are four types of carriage rides to select from, including a sleigh that seats up to six and a guided historic tour. Tickets can and should be purchased in advance here. The cost is only $10-15 per person.

Tickets are sorted by time and grouped by carriage type. Each hour one wagon ride includes historian Jan Knowles who will tell you stories about the houses you pass. To book those, look for the “History Tour” options. (At the bottom of the ticket purchase page are options for other nights.)

The Family Christmas Festival will be December 20^th with a Special Sensory-Sensitive Santa Experience

How many times do you wish there was holiday magic for those who don’t want it loud? Especially the children who may be frightened and shut down? Brooksville Main Street has taken the time to include these special children in the celebrations.

Santa returns to Brooksville on Tuesday, December 20 for free photos in Hernando Park, adjacent to the Brooksville Welcome Center.

From noon to 2pm, the park will exclusively welcome children with special needs and their families for a Sensory-Sensitive Santa Experience. “This a special offering for children with sensory issues to see Santa in a calmer, quieter environment,” says Jo-Anne Peck, President of the Brooksville Main Street Board, “Crafts, a petting zoo, pony rides, face painting and good ole St. Nick are on the roster – and it’s all free to enjoy!”

After 2pm, the fun opens to all children and their families through 5pm.

Brooksville’s Historic Homeowners provide Holiday Hospitality December 21-22

Stroll South Brooksville Avenue during carriage ride times (6-9pm) to see the historic homes along this brick-paved street and enjoy Brooksville’s holiday hospitality from the homeowners! There will be craft vendors at the water tower and homeowners along the route are decorating to impress and welcoming guests with games, snacks, crafts, and more.

“Brooksville Main Street loves bringing so many free opportunities for families to make memories with their loved ones during the holiday season. Local residents, businesses and organizations come together to fund these special events and activities through the Main Street Program. We hope you will join us December 1 and return throughout the season,” Natalie said. “With the exception of the horse drawn carriage rides, all events are free for families to attend.”

Brooksville Christmas on Main Street Guide

• through Nov. 24 – Christmas on Main Street window decorating contest for merchants. Enjoy the holiday windows and see who wins.
• through November 28 – Festival of Trees – enjoy holiday trees and wreaths decorated and donated by local residents, merchants and organizations – then bid on your favorite. If you win the bid, it will be delivered on November 28 to your door (as able). All funds raised go to fund Brooksville Main Street.
• Dec. 1 from 4 – 9 pm – Christmas Tree Lighting at 6:45 pm at Hernando County Courthouse, live entertainment, 100 vendors, Patricia’s Windows come to Life, Santa for photos, Brooksville Woman’s Club open house, kids holiday crafts at Hogan Law Firm – streets closed in downtown area.
• Dec. 1 – 31 – Holiday trees light up and synchronized to music nightly starting at 6pm
• Dec. 10 from 10am – 2:30pm – Brooksville’s 48th Annual Christmas Parade sponsored by Brooksville Kiwanis Club – Main Street closed from Hernando High School through Broad Street. Broad Street closed from Main to Bell Ave.
• Dec. 14, 15, 21, 22 from 6 – 10pm – Christmas Carriage Rides $10-15 each. Historic narration available one ride per hour. Schedule online to ensure your ride. Main Street closed between Broad and Jefferson.
• Dec. 16 – 23 – The Keys to Christmas – follow Brooksville Main Street’s website or Facebook page for the daily clue. Solve the clue, visit the location, find the key and win a $25 gift card for a downtown Brooksville Business. Clues posted daily by noon on the website and social media. Then tag #WeloveBvl to share the love!
• Dec. 20 from 12-5pm – Family Christmas Festival and Sensory-Sensitive Santa Experience in Hernando Park. Bring your special needs children between 12-2pm for a special time with Santa, crafts, a petting zoo and pony rides. From 2-5, family festival includes all the same things, only louder.
• Dec. 21-22 from 6-9pm – Brooksville’s homeowners along South Brooksville Avenue will decorate their homes for the holidays, providing games, snacks, crafts, and who knows what.