Park Avenue in Winter Park: Your 2026 Holiday Season Guide

Park Avenue now has two halves. North of Garfield Avenue, the city finished Phase 1 of the Park Avenue Refresh on schedule and marked it with a celebration at Garfield and Park on October 13. South of Garfield, along Central Park, the street looks the way it has for years. In January 2027, that stretch becomes Phase 2.

The art festival and the tree lighting happen on the southern half, and the Christmas Parade starts on the rebuilt north end before it heads down the Central Park blocks. So from now through the first weekend of December, you can walk a finished block and a waiting block in the same evening. After New Year's, the crews move south.

What the north end looks like now

Phase 1 began January 20, 2026, and was paid for by the Community Redevelopment Agency. The city's project page sets the formal Phase 1 limits at Webster to Garfield. Its fall newsletter says the actual work and new light poles ran from Swoope to Garfield. Here's what a walk up from Garfield shows you:

• New streetlights. The new dark-sky poles aim light down at the sidewalk and street. Each one was custom-built to carry Wi-Fi, security cameras, audio equipment, hanging flower baskets and street banners.
• Bump-outs at Cole and Canton. These shorten the walk between crosswalks and let pedestrians see past parked cars.
• Planter pots that do double duty. The reinforced pots act as protective bollards between traffic and pedestrians. Seasonal planting in them started the week of September 14.
• Restored brick planter beds. The beds have new stone wall caps and Liriope plantings, and some were enlarged to leave room for trees to grow.
• Work you won't see. New conduit for electric, fiber and irrigation now runs underground, along with new stormwater pipes and basins for drainage after heavy rain.

Phase 1 was backed by $2.5 million in CRA funding approved in August 2025. Bungalower puts the full three-phase project at $8.5 million. That leaves most of the budget for the two phases still ahead, and the next one covers the busiest part of the street.

The blocks next in line carry the whole calendar

Phase 2 runs from Garfield to New England. Central Park is on the west side, and on the east side are storefronts including Briarpatch, Prato, Tabla, Glass Knife and Lululemon. When the City Commission voted 5-0 in February to fund the design work, Bungalower reported that this stretch hosts major events like the Sidewalk Art Festival. That makes the construction more complicated than the north end was.

The June 10, 2026 concept presentation marks the corridor at Garfield, Lincoln, Morse, Welbourne and New England. It plans more than the north end got. The concept calls for about 11 bulb-outs, about 70 planter pots at intersections, about 130 bollards and about 38 new light poles. It also proposes three features with no match on the finished blocks:

1. An entry feature at Central Park and Lincoln.
2. A bus-stop building near Morse.
3. Possible changes to the Rose Garden. The plan lists these as a discussion with the Parks & Recreation Advisory Board, and that coordination is still listed as forthcoming.

All of these are concept-stage numbers from June. The final construction plans may differ. The project designer told Bungalower that work inside the park itself should be limited, though streetscape elements could reach into Central Park so the look matches the street.

This season's events span both halves

Every big date between now and early December happens in or beside Central Park. Some of them also spill north onto the rebuilt blocks.

The Autumn Art Festival is the only juried fine art festival that shows Florida artists exclusively. The festival closes Park Avenue from Lyman to Canton, and Canton is one of the intersections that got a new Phase 1 bump-out. That puts finished pavement at one end of the closed stretch, with the Central Park frontage that's next on the schedule along its length. If you're driving, the Chamber points to the Truist Parking Garage at 203 E. Lyman Ave. and to municipal lots around downtown, which have accessible parking spaces.

Winter on the Avenue is the season's busiest night on the Central Park blocks. The program includes the tree lighting, the Chanukah menorah lighting, strolling carolers, a snow experience, stilt-walking elves and Santa. The next morning, the Christmas Parade covers both halves. According to Visit Orlando, it starts at Cole Avenue, another new Phase 1 bump-out, and heads south down Park Avenue past Central Park before turning at New England Avenue. The Chamber calls it the oldest continuous holiday parade in Central Florida, with more than 80 organizations marching. The Park Avenue District's holiday page lists November 27 as the start of the Cathedral of Lights and Holiday Carousel. The page gives no year, so check closer to the date.

The storefronts are changing on the same timeline

Construction isn't the only change on the Avenue in 2026. According to Winter Park Voice, Park Avenue counted 3 million visitors in 2025, up from 2.7 million in 2019 and 2.1 million in 2020. The city tracks those totals with software that counts unique U.S.-based cellphone signals. On those blocks, some longtime tenants have left and new names are coming in.

Departures and moves. Tuni, the women's boutique that spent 40 years on Park Avenue, now operates from the former Miller's Hardware space at 143 W. Fairbanks Ave., according to Orlando Shine. Its own site lists that address as a pop-up with daily hours. Cocina 214 Mexican Kitchen & Bar, at 151 E. Welbourne Ave., served its last meal on May 29 when its lease ended, Bungalower reported.

Arrivals. Brandy Melville opened in April in the former Lilly Pulitzer space. Winter Park Voice reported that the line wrapped around the corner at Morse Boulevard, and that the nearby boutique Through the Looking Glass offered discounts to shoppers who showed a Brandy Melville receipt.

Coming soon, not open yet. Paradox is a steakhouse with a private members' lounge going into the former Blu on the Avenue space at 326 S. Park Ave. Its own site now gives January 2027 as the opening month, the same month Phase 2 is set to start. Oak & Stone still lists 310 S. Park Ave. as "coming soon," with no date. A block off the Avenue, The Reverie is a brasserie from chef Brandon McGlamery and Foundry Group planned for 533 W. New England Ave. WhatNow Orlando reported in August that it's aiming to open in late 2026.

Paradox's January 2027 opening and The Reverie's late-2026 target both land right around the time crews are due on the Central Park blocks. Diners at Paradox's first services in January may be walking past work zones on their way in.

What January changes on your usual walk

The north end shows how construction will probably feel. The city says Phase 1 moved one to two blocks at a time, sidewalks stayed open and Park Avenue stayed open for business throughout. When work started in January, project manager Clarissa Howard told Spectrum News 13 that lanes would close and parking would be limited block by block, while every business kept access to its front door. For Phase 2, she told Bungalower the city would keep merchants informed and keep a walkway open to every storefront.

The $240,250 contract approved in February with Stringfellow Planning & Design covers Phase 2 design, project management, community engagement and subconsultant costs, plus construction administration for Phase 1. It is not a construction budget for Phase 2. City staff have said they'll work with event organizers to fit events around construction zones, and they named the Sidewalk Art Festival specifically. Phase 3, from New England to Fairbanks, is scheduled to start in January 2028.

Howard's phrase for the whole project, quoted by Bungalower, is "fluff our feathers." The city posts updates and an eNewsletter signup at cityofwinterpark.org/ParkAveRefresh, and questions go to [email protected]. Winter on the Avenue on December 4 is the last big evening on the Central Park blocks before Phase 2 work starts.

If you own a home near Park Avenue and are wondering how a listing would come across with Phase 1 finished and Phase 2 underway, The A List can show you how we would photograph, film and present your home through each phase. Request a VIP Listing Consultation, and we'll build a timeline around the construction calendar.