On the evening of Friday, Dec. 4, the doors of a house built in 1784 open for free tours, and Santa poses for photos in its study. By Saturday evening, decorated boats are moving out of Drakes Creek toward Sanders Ferry Park. On Sunday afternoon, more than 80 parade entries head down Main Street, and the tree at Memorial Park lights up right after the last one passes.
Hendersonville's biggest holiday events of 2026 all fall in those 72 hours. Each is at a different landmark, and together they run from the region's oldest permanent home to the water to downtown. The November events beforehand are mostly at those same places, so the whole season follows one path through town.
The Season, Dated
| Date | Event | Where | Time | Cost |
|---|---|---|---|---|
| Sat., Nov. 21 and Sun., Nov. 22 | Winter Concert Series | Lakeview Hall, Historic Rock Castle | 5–9 p.m. | $75 |
| Thu., Nov. 26 | Indian Lake Loop 5-mile walk/run | The Streets of Indian Lake | 8 a.m.–noon | See organizer |
| Sat., Nov. 28 | Merry Monthaven Christmas | Monthaven Arts and Cultural Center, 1017 Antebellum Circle | Noon–7 p.m. | See organizer |
| Fri., Dec. 4 | A Merry Castle Christmas | Historic Rock Castle | 5–8 p.m. | Free, no ticket |
| Sat., Dec. 5 | Deck The Hulls Christmas Boat Parade | Drakes Creek to Sanders Ferry Park | 5:30–8 p.m. | Free |
| Sun., Dec. 6 | "A Storybook Christmas" Parade and Tree Lighting | Main Street to Memorial Park, 151 E. Main St. | 2–6 p.m. | See organizer |
The table's last three rows are the weekend. Each is at a different landmark on a different day, and they run in order: castle, then lake, then Main Street.
Friday: The Oldest House Goes First
Historic Rock Castle starts the weekend with A Merry Castle Christmas on Friday, Dec. 4, from 5 to 8 p.m. This is the 1784 home of General Daniel and Sarah Smith. For the evening, the house is decorated for the holidays and open for free tours, with refreshments, a holiday gift shop, and Santa taking photos in the historic study.
No ticket is required, and the site explains why:
"We're offering this event free to our wonderful community of friends and supporters as a thank-you for helping us preserve this historical gem of Sumner County!"
The timing matters for anyone trying to fit the whole weekend in. Friday is the only evening of the three set indoors, inside a house the site's events calendar calls the region's oldest permanent home.
Saturday: The Parade Moves to the Water
On Saturday, Dec. 5, the event moves from a house to the lake. The Deck The Hulls Christmas Boat Parade begins at 5:30 p.m. Its route is set by three named points: it starts in Drakes Creek, passes the judges' area at Mallard Park, and finishes at Sanders Ferry Park.
The parade is free to watch and free to enter. Boat owners register through HolidayFest's entry link, so any lit vessel on the water that evening belongs to someone who signed up. The organizer's slogan for the night is "Let's LIGHT UP THE LAKE."
EXS Group, FOX 17, Comcast, and Hendersonville Parks & Rec are listed as this year's boat parade sponsors. With Parks & Rec involved, the city has a direct hand in the one event on the calendar that happens on the water.
Sunday: Main Street, Then the Tree
HolidayFest's "A Storybook Christmas" Christmas Parade and Tree Lighting is on Sunday, Dec. 6, at 2 p.m. The organizer calls it the most popular event of the season. The parade goes down Main Street with more than 80 floats, trailers, dancers and entertainers, and Santa rides at the end.
The tree lighting at Memorial Park, 151 E. Main St., begins right after the parade. HolidayFest lists the whole event from 2 to 6 p.m.
One sponsor links Saturday and Sunday. ExS Group presents the Main Street parade and also sponsors the boat parade the night before, so both HolidayFest weekend events carry the same name.
Across the weekend, Santa appears twice. On Friday he is in the Rock Castle study taking photos, and on Sunday he closes the Main Street parade. A family attending all three days sees the season's biggest gatherings in a row, with each one in a different part of the city.
November Runs Through the Same Places
Two of the weekend's settings get an earlier turn in November, when Rock Castle and Indian Lake each host an event and Monthaven holds its own tree lighting.
Rock Castle first, as a listening room. On Saturday and Sunday, Nov. 21 and 22, Historic Rock Castle hosts its Winter Concert Series in Lakeview Hall from 5 to 9 p.m. Each concert features regional songwriters, heavy hors d'oeuvres, craft beer from Half Batch Brewing, and wine, and tickets are $75. Rock Castle bills the series as Middle Tennessee's premier private listening room experience. It holds one weekend of concerts each in November, January and February, so this November weekend is the last before the new year.
Indian Lake on Thanksgiving morning. The Indian Lake Loop is a 5-mile walk/run at The Streets of Indian Lake on Thursday, Nov. 26, from 8 a.m. to noon. This year is the event's 20th. It is HolidayFest's first event of the season and the only one held in the morning.
Monthaven's tree, eight days early. Two days later, on Saturday, Nov. 28, Merry Monthaven Christmas runs from noon to 7 p.m. at Monthaven Arts and Cultural Center, 1017 Antebellum Circle. There is an artisan market, food trucks and beverage vendors through the afternoon, then tree lighting and caroling at about 4:30 p.m. and Santa photos from 4 to 7 p.m.
That gives the city two tree lightings eight days apart. Monthaven lights its tree on the Saturday after Thanksgiving, and Memorial Park lights the city's tree on Main Street on Dec. 6. Santa's appearance count for the season rises to three: Monthaven on Nov. 28, Rock Castle on Dec. 4, and the end of the parade on Dec. 6.
Planning the Weekend Around the Clock
The weekend's start times make it possible to attend all three days without overlap:
- Friday, Dec. 4, 5–8 p.m. Historic Rock Castle open house, free and no ticket needed.
- Saturday, Dec. 5, 5:30–8 p.m. Boat parade from Drakes Creek past the Mallard Park judges' area to Sanders Ferry Park.
- Sunday, Dec. 6, 2 p.m. Main Street parade, followed directly by the Memorial Park tree lighting at 151 E. Main St.
The two evening events begin within half an hour of each other, at 5 p.m. Friday and 5:30 p.m. Saturday, and the Sunday parade begins in daylight. Boat owners who want a spot in Saturday's lineup and groups who want a spot in Sunday's parade both enter through HolidayFest, which has entry forms for each event on its events page.
Weekends like this are part of what our team tracks across Greater Nashville, and we enjoy passing that kind of local detail on. If you have family visiting for the holidays or questions about Hendersonville's lakeside streets, The Tate Team is glad to help. Contact Us anytime.
