In Winter Park, Saturday morning happens at one corner. The Saturday Farmers' Market runs every week from 8 a.m. to 1 p.m. in Central Park's West Meadow, at New York Avenue and Morse Boulevard. This November, two of the city's biggest events need that same meadow on back-to-back Saturdays. Cows 'n Cabs holds its main event in the West Meadow on Saturday, November 7. The 53rd Annual Winter Park Autumn Art Festival takes over Central Park on Saturday and Sunday, November 14 and 15.
The city already has a fallback for this. A few times a year, the Farmers' Market moves from the West Meadow to Seven Oaks Park so the meadow can host major events, and the city names the Autumn Art Festival and Cows 'n Cabs as two of them. Seven Oaks Park is at 1150 North Orange Avenue. For a few weeks this fall, the town's regular Saturday shifts toward a corridor most people pass through on the way somewhere else.
The fall calendar, mapped by location
The season builds up in steps. October's events are spread around town and most are free. In November, the activity concentrates in Central Park and along Park Avenue, and part of it is ticketed.
| Date | Event | Where |
|---|---|---|
| Thursday, Oct. 8, 8 p.m. | Popcorn Flicks screening of Monster House, free, with Enzian | Central Park |
| Oct. 10 through 31 | Pumpkin Patch on Park, the Park Avenue District's first | Winter Park City Hall lawn |
| Saturday, Oct. 17 | Candlelight Concert: The Best of Joe Hill | Mead Botanical Garden |
| Oct. 22 through 25 | The Bounds | Annie Russell Theatre, Rollins College |
| Sunday, Oct. 25, 11 a.m. to 3 p.m. | 25th Anniversary Community Day, free | Casa Feliz, 656 N. Park Ave. |
| Tuesday, Oct. 27, 5 to 7 p.m. | Best of Winter Park winners announced in 50 categories | Winter Park Farmers' Market |
| Thursday, Nov. 5 | Cows 'n Cabs Tapas & 'Tinis | Cows 'n Cabs |
| Saturday, Nov. 7 | Cows 'n Cabs main event | West Meadow |
| Nov. 14 and 15 | Autumn Art Festival, 9 a.m. to 5 p.m., free | Central Park and Park Avenue |
| Nov. 14 and 15 | GROWvember Fall Fest & Plant Sale, 9 a.m. to 3 p.m., free | Mead Botanical Garden |
The October entries are spread across the city. The Pumpkin Patch runs for three weeks on the City Hall lawn, and the Park Avenue District says more programming is still to be announced. The Best of Winter Park celebration happens at the Farmers' Market on a Tuesday evening, so the market's usual Saturday is not affected. November is when everything converges on the meadow.
What the meadow becomes on November 7
Cows 'n Cabs is not a quick Saturday stop. Tapas & 'Tinis on Thursday, November 5, costs $275 per person. Tickets for the Saturday main event start at $225, with General Admission, VIP and Ultimate VIP tiers. The organizer says the main event will bring more than 30 restaurants, more than 60 beverage vendors and live music to the West Meadow.
The restaurant list is mostly local. The organizer's 2026 roster includes The Ravenous Pig, Luke's, Prato, Capa, Enzo's Hideaway, Ceiba, Hawkers, Otto's High Dive, 4 Rivers Smokehouse, Gentry's BBQ, Willie's Wieners & More, Kelly's Homemade Ice Cream, Morimoto Asia, Norman's, Ocean Prime, Corner Chophouse, Space 220 and 1921 Mount Dora. Bungalower's September coverage adds Omo by Jont, Chapman, Salt and Cellar, Primo and The Reverie. The organizer says more chef and restaurant announcements are coming, so the final lineup will probably grow.
Driving changes too. The city's list of annual events with street closures includes a Cows 'n Cabs closure on Morse Boulevard. That list is organized by month and gives no closure times or exact limits for 2026. Morse is one of the two streets that meet at the market's usual corner.
Seven Oaks Park, the backup that already has what a market needs
Seven Oaks Park covers 2.4 acres, with garden areas, shade trellises, open lawn, play areas, seating, public restrooms and public parking. A produce and plant market needs open ground, shade and somewhere to park, and the city's own description lists all three.
The 2026 relocation dates are still unconfirmed. The city tells shoppers to follow its social media and check the market page for specific relocation dates. As of the end of September, that page doesn't list any fall Saturdays. November 7 and November 14 are the obvious candidates, since both are Saturdays with major events in the meadow. Until the city posts the dates, they are a reasonable guess and nothing more.
On a relocation Saturday, the vendor standards don't change, because the city runs the market the same way wherever it sets up. Every vendor needs a sales tax number. Consumable products must be licensed through the State of Florida, and the city does not accept cottage food items, resale merchandise or packaged, nationally distributed foods.
North Orange Avenue gets a turn
Moving the market puts the Saturday crowd within a short stretch of a corridor that has added new businesses this fall. Seven Oaks Park sits at 1150 North Orange Avenue. The nearby blocks include:
- Viet-Nomz, 1330 N. Orange Ave. ClickOrlando reported the new Winter Park location as open on September 16.
- The Courtesy, 1288 N. Orange Ave. Its Nightmare on Orange Halloween takeover runs from September 22 through November 1, with seasonal cocktails, themed décor, walk-in seating and reservations.
- Black Phin Coffee Bar, Harmon Collective, 1152 Harmon Ave. The coffee bar leaves Harmon Collective after October 11. Owners Saeng and Linda Khouvongsavanh say they are looking for a brick-and-mortar location of their own and are not closing for good.
The Courtesy's takeover ends on November 1, a week before Cows 'n Cabs, so the two don't overlap. Viet-Nomz is the newest of the three and is still open after the Halloween season. Black Phin's next location hadn't been announced when Bungalower reported the move on September 30.
November 14 and 15, when two festivals share one weekend
The Autumn Art Festival weekend is the busiest of the fall because a second free festival runs across town on the same two days.
In Central Park, the Winter Park Chamber of Commerce reports that the Autumn Art Festival will feature 186 artists, all from Florida. The residency rule requires each artist to keep a principal residence in the state. Park Avenue closes to traffic from Lyman Avenue to Canton Avenue on both festival days. The Chamber points visitors to parking on surrounding streets, handicap spaces in municipal lots, the Truist Garage at 203 E. Lyman Ave. and the Canton Avenue Garage at 150 E. Canton Ave. The Chamber's food and drink page lists catered VIP lunches and a beer garden. As of late September, details on children's art and entertainment were still marked "check back closer."
At Mead Botanical Garden, GROWvember Fall Fest & Plant Sale runs both days from 9 a.m. to 3 p.m. It's free and includes vendors, kids' activities, live music, food trucks, a beer garden and a city tree giveaway. GROWvember wraps up two hours before the art festival does.
That gives the November 14 weekend three possible plant-buying stops: the Farmers' Market, whether it stays in the meadow or moves to Seven Oaks, the GROWvember plant sale, and the city's tree giveaway at Mead. On a normal Saturday, the market is the only one.
Park Avenue changed over the summer
Anyone heading to the art festival will find a different Park Avenue from the one they shopped last November. Lilly Pulitzer is now open at 301 S. Park Ave., the corner storefront Tuni held for 40 years. Tuni stayed in Winter Park and moved to a temporary pop-up at 143 W. Fairbanks Ave. In late August, Louise James Boutique at 214 N. Park Ave. announced it would close. Owner Katie Bullivant hadn't set a final date, and the shop was still open with a clearance sale. Garp & Fuss closed temporarily after a fire, and the July report gave no timeline for reopening.
Another business is on the way. Bungalower reports that Nigel's Bananas is headed to 334 N. Park Ave. with a February 2027 target, though the company hasn't announced an opening date. Saikō Coffee owner Josue Villacis is planning a Winter Park café built around matcha, coffee, pastries and house-made syrups. The location and opening date haven't been disclosed yet.
Two recent openings off the avenue are worth a stop on a festival walk. Baby John's Ice Creamery, owned by John and Tiia, opened at 129 W. Fairbanks Ave. on June 13 and serves Hershey's Ice Cream. La Diperie, a Montreal-born shop selling customizable dipped ice cream, opened by July 12 at 501 N. Orlando Ave., Suite 317.
After the festivals
The fall season tapers off after the art festival. Rollins College's Annie Russell Theatre stages the Expressions dance program November 20 and 21, and Mead Garden's Candlelight Concert series ends the month with The Best of Hip-Hop on Strings on November 28. Once the Autumn Art Festival tents come down, the West Meadow is open again for the Saturday market.
The Baldor Group pays close attention to calendars like this one, because the weeks a city's routine changes are when local knowledge makes the biggest difference. If you'd like to talk through how Winter Park's busy November weekends affect showing schedules, open houses or the timing of a move, Bobby Baldor and the team are glad to help. Contact Us.
