Most of what Hendersonville puts on for the 2026 holidays is free, and most of it lands within about 24 hours. The lighted boat parade goes out on Old Hickory Lake at 5:30 p.m. on Saturday, December 5. The Main Street parade starts at 2 p.m. the next afternoon, and the tree lighting at Memorial Park follows it. November is different. The events come one at a time, in different parts of town, and they rarely run into each other.
So the November events are easy to fit in. The first weekend of December takes some planning, because two of its events have times that overlap.
November runs one event at a time
The season starts Friday, November 6. The GFWC Woman's Club of Hendersonville holds its Mistletoe Market on Friday and Saturday, November 6 and 7, in St. Joseph's Hall at Our Lady of the Lake Catholic Church. Friday evening is VIP shopping with sangria, door prizes and vendor specials. Saturday is the regular shopping day, and the first 50 people in line get swag bags. The club notes that it is not affiliated with the church.
After that comes a three-week gap, then two events close together over the Thanksgiving holiday.
| Date | Event | Where | Time | Cost |
|---|---|---|---|---|
| Fri., Nov. 6 | Mistletoe Market VIP shopping | St. Joseph's Hall, Our Lady of the Lake | 5 to 8 p.m. | Not listed |
| Sat., Nov. 7 | Mistletoe Market | St. Joseph's Hall, Our Lady of the Lake | 9 a.m. to 4 p.m. | Not listed |
| Thu., Nov. 26 | Indian Lake Loop 5 Mile Walk/Run | Streets of Indian Lake | 8 a.m. to noon | Registration required |
| Sat., Nov. 28 | Merry Monthaven Christmas | 1017 Antebellum Circle | Noon to 7 p.m. | Free |
This is the 20th year of the Indian Lake Loop. HolidayFest's race page tells runners to grab their favorite turkey outfit, and it also says same-day registration is now allowed. If you run it Thursday morning, you still have the rest of Thanksgiving for the meal.
The town lights two trees, eight days apart
Hendersonville has two tree lightings this season, and they are eight days apart.
The first is at Monthaven Arts & Cultural Center on the Saturday after Thanksgiving. This is the fifth annual Merry Monthaven Christmas. It runs from noon to 7 p.m., and the tree lighting and caroling start around 4:30. Santa takes photos from 4 to 7 p.m. There is also a holiday artisan market, plus food trucks and drink vendors. Visitors can see the center's exhibit David Wright: An American Master and its small works show, Dreaming of an Artful Christmas. Admission is free.
The second is the city's tree lighting at Memorial Park, 151 E. Main St., which starts right after the Christmas parade on Sunday, December 6.
Monthaven's lighting happens at a slower pace. People are already on the grounds shopping or touring the galleries when the caroling starts, and the day runs for seven hours. Memorial Park's lighting comes at the end of a parade with more than 80 entries. If you have small kids who would rather not wait out a crowd, Monthaven's lighting is the easier trip. Its Santa photo line also runs a full week earlier than the ones in December.
One nonprofit runs most of December
Most of the big December events come from one organizer. HolidayFest is a nonprofit community service group that organizes annual events in Hendersonville and nearby Sumner County communities from July through February. Many of those events center on Thanksgiving and Christmas.
The group began in the 2007 Christmas season, when a gingerbread competition was paired with the Hendersonville City Parade to make a small festival. By 2014, HolidayFest was hosting 18 events.
HolidayFest puts on the Indian Lake Loop, the boat parade and the street parade, so it decides which weekend everything lands on. In 2026, it scheduled the water parade and the street parade for back-to-back days.
Saturday, December 5: the parade is on the water
The 2026 Deck the Hulls Christmas Boat Parade starts at 5:30 p.m. on Saturday, December 5, and the listing runs until 8 p.m. Boats start in Drakes Creek, pass Mallard Park, where the judges are stationed, and finish at Sanders Ferry Park.
It costs nothing to watch and nothing to enter a boat. EXS Group, FOX 17, Comcast and Hendersonville Parks & Rec present the parade.
The two parks along the route are set up very differently for watching:
- Mallard Point Boat Launch is the judges' area. The city lists only a boat launch and picnic tables there.
- Sanders Ferry Park is where the route ends. The city lists picnic shelters, a playground, an accessible boat and fishing pier, and restrooms.
If your group has kids or older relatives who will want a restroom during a December evening outside, Sanders Ferry Park is the better spot. If you want to see the boats while the judges are watching, Mallard Point is the place. Since the parade ends at Sanders Ferry, people watching there see each boat at the end of its run.
Sunday, December 6: Main Street at 2 p.m.
The next afternoon, HolidayFest's "A Storybook Christmas" Christmas Parade and Tree Lighting starts at 2 p.m. ExS Group presents it. 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 comes right after.
This is where the times overlap. Historic Rock Castle holds A Merry Castle Christmas from 3 to 6 p.m. It's a free tour of the 1784 home of General Daniel and Sarah Smith, with refreshments, a holiday gift shop and Santa photos. No ticket is needed, and the site calls the event a thank-you to the people who help preserve it.
Rock Castle's event page gives the date as "Saturday, December 6, 2026." December 6 falls on a Sunday this year. Check with Rock Castle before you go, because either day causes an overlap:
- If it's Sunday the 6th, the open house starts an hour into the parade. People can catch the end of the parade, or go to Rock Castle once the floats pass and before the tree lighting.
- If it's Saturday the 5th, the open house ends at 6 p.m., half an hour after the boats leave Drakes Creek. Going from the Rock Castle tour straight to a lakeside park makes for a full afternoon and evening.
Either way, there are three Santa photo chances in a single weekend, at Rock Castle, on the parade's last float and at the tree lighting, plus Monthaven's the week before. Families who skip one still have others.
The weekend at a glance
All times are as listed by the organizers.
- Saturday, 5:30 p.m. The Deck the Hulls boats leave Drakes Creek, pass the judges at Mallard Point and head toward Sanders Ferry Park. The listing ends at 8 p.m.
- Sunday, 2 p.m. The "A Storybook Christmas" parade starts down Main Street.
- Sunday, 3 to 6 p.m. A Merry Castle Christmas at Historic Rock Castle, if Sunday is the right date.
- Sunday, after the parade. Tree lighting at Memorial Park, 151 E. Main St.
HolidayFest's site lists the street parade from 2 to 6 p.m., so the whole thing, tree lighting included, fits inside one afternoon.
Getting into the parade
If you'd rather ride in a parade than watch it, the sign-up deadlines come well before December.
To enter the boat parade, boat owners sign up through HolidayFest's "Enter Your Vessel" link, and it's free.
According to HolidayFest's parade entry page, the street parade costs $75 for businesses and individuals and $35 for churches, civic groups and schools. City officials enter free. HolidayFest takes no entries after November 15. Every entry must also send someone to a parade orientation on Thursday, November 19, at 10 a.m. or 7 p.m. in the meeting room at City Hall, 101 Maple Dr. N. Entry numbers and parade-day instructions are given out at that meeting. HolidayFest takes questions at [email protected].
That means a church group or neighborhood float has two Hendersonville dates in November, the entry deadline and the orientation, and both come before the Indian Lake Loop is run.
If your relatives come in for the parade weekend and start asking what it would be like to live near the lake or close to Main Street, I'm happy to talk it through. I'm Shawn Wright with CENTURY 21 Wright Realty, and I can tell you how Hendersonville compares with other places across Middle Tennessee, without any pressure. Let's Connect.
