Anyone who circles the second weekend of October for the Winter Park Autumn Art Festival will find Central Park quiet. The 53rd edition runs Saturday and Sunday, November 14 and 15, 2026, from 9 a.m. to 5 p.m. Admission is free. Last year's festival was October 11 and 12.
The Chamber of Commerce's own event listing still carries a line about hosting the festival on the second weekend in October, right above the November dates. Chamber CEO Ann Marie Cooper gave the City Commission the November dates on August 26. The Park Avenue fall that many older listings describe is last year's. The 2026 version starts its big events in mid-November, and it arrives with the streetscape work finished and several restaurants still unopened.
Three Dates Inside Three Weeks
| Date | Event | Where |
|---|---|---|
| November 14 and 15 | Autumn Art Festival | Central Park, 251 S. Park Avenue |
| November 27 through January 3, 2027 | Holidays on Park, with the Cathedral of Lights and the Holiday Carousel | Park Avenue and Central Park |
| December 4 | Winter on the Avenue | Central Park and Park Avenue |
Some pages still say the holiday setup begins November 13. That was the 2025 start. This year the Park Avenue District and VisitFlorida list November 27, the Friday after Thanksgiving. The festival ends Sunday, November 15, so twelve days pass before the first light goes on. The art festival takes place on Park Avenue with no holiday decoration around it.
It also draws a different crowd than March. The Autumn Art Festival features more than 180 artists and draws about 150,000 visitors, all from a field limited to artists whose principal residence is in Florida. The March Sidewalk Art Festival draws roughly 250,000. The fall show is the smaller of the two. Judging happens Saturday morning starting at 9 a.m., with Best of Show carrying a $5,000 award. The Saturday-night Artists' Party begins at 5:30 p.m. at the Winter Park Farmers' Market.
The logistics are worth planning around:
- The Chamber's festival guide has described Park Avenue closing to traffic from Lyman to Canton avenues on both festival days.
- Parking is available at the Truist garage at 203 E. Lyman Avenue and the Canton Avenue garage at 150 E. Canton Avenue.
- Pets are not allowed in Central Park.
- SunRail stops at the Winter Park station beside Central Park.
The Crews Finish Before the Lights Go Up
Phase 1 of the Park Avenue Refresh covers Webster Avenue to Garfield Avenue. It started January 20, 2026, and is funded by $2.5 million from the Community Redevelopment Agency. The work replaces streetlight poles with new fixtures that carry smart hubs, banner arms, and hanging baskets. It adds reinforced planter boxes made with concrete and rebar, which double as barriers against vehicles entering pedestrian areas, along with bollards at chosen points.
City communications director Clarissa Howard said on September 1 that this phase will wrap before the holiday shopping season starts. Crews began installing the new planters in early September. The work has moved one to two blocks at a time, closing the right-of-way, the adjacent parking spaces, and one southbound lane on each block. The city put temporary parking on Morse Boulevard between New York and Virginia avenues to cover the losses.
The timing works out cleanly. The festival on November 14 and 15 sits on the Central Park side of the avenue, which belongs to Phase 2 and has not been touched. Phase 1 finishes on the northern blocks in time for the Cathedral of Lights on November 27. The holiday setup goes in as the Phase 1 planters and lights wrap up.
Which Openings Are Actually Open
Several restaurants have been described for months as arriving "this fall." As of late September, the record for each reads differently.
- PopUp Bagels has been open since May 29 at 646 S. Orlando Avenue, near Fairbanks, in the former Soho Juice Co. space. It serves hot, unsliced bagels meant for tearing and dipping. At launch, a bag with a three-bagel minimum and one schmear was $13. The lot is small.
- The Grove Bar + Kitchen, from Chef Mario Pagan, replaced Chayote Barrio Kitchen at Winter Park Village. The restaurant's website now carries The Grove name and takes reservations through OpenTable.
- Oak & Stone at 310 S. Park Avenue is still listed as coming soon on the company's own location page.
- The Reverie at 533 W. New England Avenue lists a late 2026 opening on its own website.
- Mecatos Bakery & Cafe was announced for the old Coop building on the southwest corner of Morse Boulevard and Pennsylvania Avenue, with the timing given as some time in 2026.
Oak & Stone's slide is the clearest of these. Artistry Restaurants announced the concept in January 2025 for the former 310 Park South space and said it would open later that year. 310 Park South had closed on New Year's Eve after more than 25 years. Artistry already runs Boca, Atlantic Beer & Oyster, and The Chapman on the avenue. The new room promises 12 styles of artisan pizza and a self-serve beer wall with 40 to 60 taps. Twenty months after the announcement, the location page still says coming soon. Anyone planning a November dinner around it should call ahead.
The Reverie has a longer run-up. Chez Vincent held its last service on Sunday, December 21, 2025, after 28 years in Hannibal Square. Chef Brandon McGlamery, a two-time James Beard nominee who cooked at Luma on Park, Prato, and Luke's Kitchen + Bar, is opening his first independent concept there with Foundry Hospitality. The room will have a full bar and a cellar-inspired private dining space. The Gagliano family kept the property and is the landlord. The restaurant's Instagram account, @thereverie_wp, is the place to watch for an opening date.
Mecatos raises a different question. The Coop closed in July 2023, and the building sat vacant for more than two years before the announcement. Mecatos was founded in 2015 by Edwin Lurduy and runs nine locations, with empanadas, buñuelos, and pan de bono among its signature items. The building's red-barn facade has practically reached landmark status in Winter Park, and it is unclear whether Mecatos will keep it.
Oak & Stone, The Reverie, and Mecatos have no confirmed opening date, and the fall events begin on November 14.
Where the Crews Return in January
Phase 2 is targeted for January 2027 and covers Garfield Avenue to New England Avenue, including the Central Park frontage. The City Commission voted 5-0 on February 25, 2026, to approve a $240,250 design contract with Stringfellow Planning & Design. The design team plans to study the Morse Boulevard and Park Avenue intersection, the Rose Garden entry, and the edges of Central Park. Phase 3, from New England Avenue to Fairbanks Avenue, is expected in January 2028. The three phases together are projected at $8.5 million.
Phase 2's window overlaps the 68th Winter Park Sidewalk Art Festival, scheduled for March 19 to 21, 2027, the same Central Park frontage that hosts the fall festival. The city has posted numbered project updates since the work began, with Update 20 dated August 24, 2026.
The Phase 2 blocks along Central Park are the ones that change next. For an owner near the avenue weighing what the 2027 rebuild means for a Winter Park home, Nest Seekers Orlando can help. Speak With a Global Advisor.
