The snow at The Village Shops on Venetian Bay comes twice this year, three weeks apart. The Village has posted a holiday calendar with two Saturday evenings that share almost the same program. Both run from 3 to 7 p.m., both have Santa and carolers, and both have a snow show at 6 p.m. Three smaller events fall in the stretch between them.
As of Thursday, October 29, the first of those evenings is a little over three weeks away. The full season fits on one page.
The Season on One Page
The Village's event calendar lists five events for November and December 2026, all at 4200 Gulf Shore Blvd. North.
Date | Event | Hours | What sets it apart |
|---|---|---|---|
Sat., Nov. 21 | Grand Illuminations | 3–7 p.m. | Tree lighting, snow show at 6 p.m. |
Thu., Nov. 26 | Gobble Gobble Thanksgiving Day 5K | Race at 7:30 a.m. | Benefits St. Matthew's House |
Fri.–Sun., Nov. 27–29 | Black Friday Stroll & Shop | 10–7 Fri. and Sat., noon–6 Sun. | Three-day shopping weekend |
Thu., Dec. 10 | Santa Paws | 4–7 p.m. | Free pet photos with Santa |
Sat., Dec. 12 | Holiday on the Bay | 3–7 p.m. | Second snow show at 6 p.m. |
Read top to bottom, the calendar is a pair of Saturday bookends with the quieter events in between. Each event in the middle is aimed at a different part of the community: runners on Thanksgiving morning, shoppers over the long weekend, and dog owners on a Thursday evening in December.
The First Saturday Lights the Tree
Grand Illuminations opens the season on Saturday, November 21. According to the Village's event page, the evening includes complimentary photos with Santa, Dickens Carolers and festive character appearances. As it gets dark, what the Village calls Naples' tallest Christmas tree lights up along with more than 100,000 lights throughout the property. The snow show starts at 6 p.m.
The timing matters. A 3 p.m. start leaves enough daylight to walk the waterfront first, and the 6 p.m. snow comes after the lights are on. The tree lighting happens only once, on November 21. Every later visit this season is to a tree that's already lit.
The Week the Calendar Fills Up
The five days after Grand Illuminations hold two events that bring in different crowds.
The Gobble Gobble Thanksgiving Day 5K is on Thursday, November 26. Announcements begin at 7:20 a.m., and the race starts at 7:30 a.m. The Village calls it Naples' original Thanksgiving Day race, and the course runs past the waterfront and through nearby Naples streets. Thanksgiving-themed outfits are encouraged, and you can walk or run it. The race supports St. Matthew's House, and the Village says it has long raised tens of thousands of dollars for the organization. Registration is through Run Elite Events.
If you're hosting family that week, the 5K takes about a morning and leaves the afternoon open. With a 7:30 a.m. start, runners are done well before the turkey goes in.
Black Friday Stroll & Shop runs the next three days. Hours are 10 a.m. to 7 p.m. on Friday and Saturday and noon to 6 p.m. on Sunday. Sunday has the shortest hours and the latest opening, so plan around that if guests leave Sunday afternoon.
A Thursday for the Dogs
Santa Paws is on Thursday, December 10, from 4 to 7 p.m. The Village offers complimentary photos of pets with Santa. It's the only weeknight evening on the calendar, and it comes two days before the second snow show. If you plan to come to both, you'll be at the Village twice in one week.
The Second Saturday Repeats the Snow
Holiday on the Bay, on Saturday, December 12, has the same hours as Grand Illuminations, 3 to 7 p.m. It also has Santa photos, carolers, waterfront lights and snow at 6 p.m.
The difference is the timing. November 21 opens the season. By December 12, the tree has been lit for three weeks, Thanksgiving is over, and the calendar is getting close to Christmas. If your family can only make one snow night, choose based on what else you're fitting around it. Grand Illuminations is the night the tree is first lit. Holiday on the Bay is the better choice if guests don't arrive until December.
The Saturday pattern also continues past the Village. One week after Holiday on the Bay, the Marine Industries Association of Collier County lists the Naples Bay Christmas Boat Parade for Saturday, December 19, from 6:15 to 8:30 p.m. Its listed viewing spots include Naples City Dock, Pinchers Tin City, Riverwalk Restaurant, Naples Landing, Kelly's Fish House, The Boat House and Bayview Park.
Dinner After the Snow
Apart from the morning 5K, every event on the calendar ends in the early evening, and the Village's restaurants sit on the water. In a feature published October 14, the Village names six of them: Bayside Seafood Grill & Bar, Fish Restaurant, M Waterfront Grille, MiraMare Ristorante, T-Michaels Steak & Lobster House and The Village Pub.
On the two Saturdays, the snow show starts at 6 p.m. and the events close at 7 p.m. That makes a 7 p.m. dinner reservation the obvious choice for families who want both. Both nights fall on weekends during the holiday season, so book early.
The Roundabout That Won't Affect This Season
Earlier this year, it looked as if roadwork might overlap with the holidays. On April 2, Gulf Coast News reported that the City of Naples was moving forward with a roundabout at Crayton Road and Harbour Drive. The report said construction was expected to start in the summer and take about 10 months.
That schedule has slipped. The City's project page still lists the intersection as "In Design." The City's request for construction proposals, RFP 26-025, was issued September 22 and closed October 22. The project budget is $1,600,000. The next steps in the solicitation are an evaluation committee meeting the week of October 26, a ranking of the bidders, negotiation with the top-ranked firm, and then a contract sent to City Council for approval.
The RFP also says when the City wants the work finished:
"The City is particularly interested in completing this project by July 1st, 2027. The selection criteria will favorably consider the contractor that can realistically accomplish this goal with as little disruption to traffic, businesses, and property owners as possible."
The selected contractor will have to prepare phased traffic-control plans, but that work comes after the contract is signed. As of this week, no contractor has been named, City Council hasn't approved a contract, and no closures have been announced for the intersection. All five Village events this season fall on a road network that hasn't changed. The roundabout is a project for the months before July 2027, and the City's own documents describe it that way.
Your Season, Date by Date
- Saturday, November 21: Grand Illuminations. The tree lighting, with snow at 6 p.m.
- Thursday, November 26: Gobble Gobble 5K. Announcements at 7:20 a.m., race at 7:30 a.m.
- November 27–29: Black Friday Stroll & Shop. Sunday has the shortest hours.
- Thursday, December 10: Santa Paws, 4 to 7 p.m.
- Saturday, December 12: Holiday on the Bay. The second snow show at 6 p.m.
Holidays in Park Shore and Seagate are some of the best times to see what these neighborhoods are like. If your plans this season include thinking about your own home's value before the new year, Janine Monfort can offer a neighbor's perspective and a clear, current read on your property. Get Your Instant Home Valuation, and enjoy the snow on the bay.
