The Sequoia on Second Street Joins Ashland's Festival of Light This Year

When Drew Gibbs's family bought the Winchester Inn in 1983, the sequoia on the property was about 10 feet tall. That was small enough for the family to string Christmas lights on it themselves, and for the first several years they did. Then the tree kept growing and the lights couldn't keep up. Ashland.news reported on Oct. 19 that Gibbs now estimates the tree is more than 50 years old and about 100 feet tall. The paper's photo caption puts it at 104 feet.

On Friday, Nov. 27, that tree at 35 S. Second St. will be lit from its lowest branches to its crown for the first time in about 40 years. The timing is deliberate. The sequoia is set to light along with downtown's Grand Illumination, and the plan is to do it again every year.

So the 34th Festival of Light has a new landmark that's just off the main drag, and it's built to last.

Nov. 27 now has two lightings

The Festival of Light kickoff will feel familiar. What's new is a second lighting, a short walk off the parade route. Travel Ashland's festival page and the Ashland.news report give the evening in this order:

1. 3 p.m.: Live music, snacks and reindeer games start on Ashland Plaza.
2. 5 p.m.: Santa's procession and the holiday parade step off. The parade traditionally runs from the Ashland Public Library area down East Main Street into the Plaza.
3. After the parade: The Grand Illumination switches on more than 1 million lights downtown, followed by music and community caroling on the Plaza.
4. Same evening: The Winchester Inn plans to light the sequoia along with the Grand Illumination, with public celebrations at Alchemy Restaurant and Bar and at Chateaubriand 36, the steakhouse that's part of Gibbs's Winchester Properties.

The Chamber of Commerce and Travel Ashland produce the festival, which runs from the day after Thanksgiving through the end of the year. That makes Nov. 27 the night the Plaza lights and the sequoia come on together. For the rest of the season, they're two stops on the same evening walk.

How you light a 104-foot tree without cutting a branch

Lighting a living sequoia takes a different kind of crew than lighting a building. Gibbs hired City Lights, the company owned by Kevin Huggins that installs and maintains downtown Ashland's holiday lighting. Ashland.news reports that Huggins has been installing lights in the Rogue Valley for 22 years.

The street sets the method. The grade on that stretch of Second Street is steep enough to make machinery impractical, so a certified arborist is climbing the tree and stringing the lights entirely by hand. Ashland.news photographed the crew hoisting strings up the trunk on a rope system.

The design is about protecting the tree:

• No cutting: Gibbs told Ashland.news that using a certified arborist means nothing is cut or trimmed during installation.
• Low heat: The display is all LED, and LEDs give off little heat.
• Remote shutoff: The whole system can be switched off remotely.
• Lights only: There are no oversized ornaments or traditional decorations. City Lights built more than 30 custom warm-white LED sets that hang down the tree.

Gibbs also makes a bigger claim. He told Ashland.news the sequoia "will actually be the tallest fully decorated living Christmas tree in the United States." He acknowledged that some communities have taller trees but said they aren't lit all the way up. Ferndale, California, he noted, has a taller tree whose lights go only partway up and only on the side facing Main Street. The record is his claim. What residents will see for themselves is a tree lit from the street all the way to the top.

The lights stay up after New Year's

This is why the sequoia matters beyond one December. According to Ashland.news, they'll stay in place year-round, with maintenance on a five-year cycle.

Leaving the lights up is what makes the tree a tradition. Gibbs told the paper he plans to tie the sequoia's lighting to the Festival of Light every year. He credited his business partner David Gualtiere, who led the renovation of the Chateaubriand 36 steakhouse terraces, with pushing the long-discussed idea into reality this year.

"We very much envision this to be an ongoing tradition. The hope is that this can provide yet another reason for people to visit the town in the holiday months and enjoy everything that Ashland has to offer."

That's Gibbs, as quoted by Ashland.news. He also talked about a childhood habit of sneaking out of his room at night to turn on the Christmas tree lights, and said he expects that same feeling watching a tree he's known his whole life lit from top to bottom.

If you live here, 2026 is the first year of what's meant to repeat. The sequoia will be part of downtown's backdrop every Thanksgiving weekend from here on.

December builds out from Second Street and the Plaza

The new tree also anchors the Winchester Inn's own holiday tradition, which has a much longer history. This is the 39th year of the inn's Dickens' Feast, a five-course holiday dinner with a quartet of carolers between courses. It ends with a cheeky Santa who hands each guest a small gift, and Gibbs calls the evening "dinner and a show." The feast took a pause during the COVID pandemic and is back this year.

Nearby, the festival calendar adds one event that has never happened before, plus a few you may know:

The Dickens' Feast runs three nights a week for three straight weekends. If you've meant to go for years, this is a good season to book. By the first seating on Dec. 3, the sequoia outside will have been lit for nearly a week.

The Sip & Shop is the Festival of Light's newest addition. Ashland.news describes it as an afternoon for exploring holiday offerings at participating local businesses "while enjoying a sip of something special along the way." Travel Ashland has posted an announcement for it, and the page also says a Santa Scavenger Hunt and a caroling schedule are coming. Check the Festival of Light page as those dates are filled in.

The far edge of the season is up the mountain

The festival page also points uphill. "Ski on Mt. Ashland or skate down in town at the Ice Rink in Lithia Park," it reads.

Mt. Ashland's operating schedule shows Saturday, Dec. 12, as its first scheduled open day for the 2026–27 season, and the ski area says that depends on weather. Regular hours are 9 a.m. to 4 p.m. Twilight skiing runs until 9 p.m. on Thursdays, Fridays and select Saturdays. That's the same weekend as Santa at Carpenter Hall. If the snow cooperates, Dec. 12 and 13 could be the busiest weekend of the season, with Santa in town and skiing on the mountain.

Lift replacements start in 2027. In its chairlift replacement update, Mt. Ashland says both existing lifts will stay safe and operational for 2026–27. It plans to replace the Windsor lift in 2027 and the Ariel lift in 2028. The ski area also notes the new lifts won't add terrain. If the plan holds, the Windsor lift running this winter is the one due to be replaced next year.

At The Parsagian Group, we love watching traditions like this get started in the towns we serve. If you're planning holiday weekends around Ashland and want ideas for the rest of the Rogue Valley this season, or you just want to talk about what's new close to home, Let's Connect.