The corner of Liberty Street and South Brooksville Avenue has a new neighbor. Under the Olive Tree opened on October 10 at 26 E. Liberty St., next to Brooksville's historic water tower. This Saturday, November 21, Brooksville Main Street's Downtown Street Market sets up at that same intersection, under that same tower, from 10 a.m. to 2 p.m.
That puts downtown's newest shop and its monthly market on the same corner for four hours. Two other spots fill the rest of the day. One closes after lunch and the other opens just as the market packs up. Plan around the clock and Saturday runs from breakfast to evening without any dead time.
The Shop Beside the Water Tower
Under the Olive Tree is a tasting room first and a store second. The shop carries ultra-premium extra virgin olive oils, aged balsamic vinegars, artisanal sourdough, and pantry staples like spice blends, teas, coffees, pastas, dipping herbs, and charcuterie board essentials. It also puts together custom gift boxes. Nature Coaster counts more than 50 oil and balsamic varieties to taste.
Owner Dawn Triconi told the Hernando Sun how the shop works:
"We are an interactive tasting room designed to inspire food lovers and home cooks alike. Guests are invited to slow down, explore, and sample ultra-premium, fresh-crushed extra virgin olive oils, aged dark and white balsamics, and fresh-baked artisanal sourdough bread before making a choice."
Downtown regulars may know Triconi already. She was most recently director of Brooksville Main Street, the same organization that runs the street market outside her door. She runs the shop with Christie Williams, former retreat manager at Chinsegut Hill, and Tracy Hebert, office manager at Accent Aluminum. The Hernando Sun reported the owners' plan to stay open seven days a week, 10 a.m. to 6 p.m.
Saturday Lands at Its Door
The Downtown Street Market comes once a month. Brooksville Main Street describes it as a gathering of local farmers, bakers, producers, artisans, shops, and restaurants. November's theme is "Thankful Friendsgiving." The market fills the intersection of Historic S. Brooksville Avenue and Liberty Street, "right underneath the Iconic Brooksville Water Tower."
The timing matters for the tasting room. Thanksgiving is five days later, on November 26. Under the Olive Tree's events page lists a November workshop with a Thanksgiving-host theme and a December workshop built around the holidays. The shop asks people to email for details. If you're hosting next week, the market puts the oils, the sourdough, and the gift boxes on your path while you're already downtown with a shopping bag.
The Day Runs in Three Shifts
Here's how Saturday, November 21 lines up. Each business's posted hours set the shifts.
| Stop | Address | Saturday hours | What it covers |
|---|---|---|---|
| Brooksville Bagels | 330 Ponce de Leon Blvd. | 6:30 a.m. to 2:30 p.m. | Breakfast and lunch |
| Downtown Street Market | S. Brooksville Ave. at Liberty St. | 10 a.m. to 2 p.m. | Midday, outdoors |
| Under the Olive Tree | 26 E. Liberty St. | 10 a.m. to 6 p.m., as planned | Midday through late afternoon |
| Good Time | 500 S. Broad St. | 2 p.m. to midnight | Afternoon into night |
Three of the four change over around 2 p.m. The market wraps up, Good Time opens its doors, and the bagel counter closes half an hour later. The tasting room keeps going after all of them. A full Saturday could look like this:
- Morning at Brooksville Bagels. Nature Coaster featured the shop as a new arrival in September, naming owners Anastasia and Mike. It serves New York-sourced bagels, made-to-order specialty sandwiches, eggs cooked to order, and a four-flavor cream cheese flight, with fresh lemonade, matcha, and cold brew to drink. One planning note: it's closed Wednesdays, so it won't work for a midweek breakfast.
- Midday under the water tower. Walk the market between 10 and 2, then step into Under the Olive Tree to taste before you buy.
- Afternoon on South Broad. Good Time opens at 2 p.m. on Saturdays and stays open until midnight.
The 2 p.m. Handoff on South Broad
Good Time isn't one of the fall's openings, but it's what makes the afternoon shift work. Per a City of Brooksville business spotlight, Daniel and Darby Pritz opened it as the second Brooksville location of Mountaineer Coffee, whose first shop dates to 2016. The building is a converted service station with a large covered outdoor seating area, in the newly expanded western part of Brooksville's Community Redevelopment Area. Mountaineer roasts its coffee daily.
The Good Time site lists natural wine, Florida beer, specialty coffee, mocktails, and ice cream. It posts Monday through Thursday hours of 2 p.m. to 11 p.m. and Sunday hours of 11 a.m. to 6 p.m. It also features Poke 'Em, a food truck serving made-to-order bowls inspired by Hawaiian and Asian flavors. Hours can shift with the season, so check the site before you build an evening around it.
The covered patio fits the late-November calendar. You can carry a market morning and a tasting-room stop into the evening without heading home first.
What the Water Tower Corner Has Next
Saturday is the middle of a busy stretch downtown. Brooksville Main Street has dates on the books from tonight through the first week of December:
- Thursday, November 19, 5:30 to 6:30 p.m. The community dedication of the Dr. Dennis Wilfong Memorial Sleigh, on the Hernando County Courthouse lawn. It's free and open to the public.
- Saturday, November 21, 10 a.m. to 2 p.m. The Thankful Friendsgiving Downtown Street Market at S. Brooksville Avenue and Liberty Street.
- Saturday, November 28, 10 a.m. to 2 p.m. Small Business Saturday, the second Saturday in a row that downtown is set up for a 10-to-2 visit.
- Saturday, December 5, 3 to 9 p.m. Christmas on Main and the tree lighting.
The December 5 hours turn the usual pattern around. Christmas on Main starts at 3 p.m., after Brooksville Bagels has closed for the day, and its evening runs alongside Good Time's Saturday hours. The November market days line up with the bagel counter and the tasting room, while December 5 lines up with the tasting room's last hours and Good Time's evening.
For more on the downtown calendar, our earlier look at how downtown Brooksville runs on two calendars covers the courthouse square and the Good Neighbor Trail. The Brooksville neighborhood page collects everything else we've written about the area.
I keep track of what opens around Brooksville because knowing a town at this level is part of how I protect my clients. If you're thinking about your own place in town, or want a straight read on what a new block of businesses means for your street, Alicia Chapman and the Tampa Top Team are ready. Schedule Your Strategy Call.
