Heads Up: Halloween Returns to the Square

On Oct. 31, Halloween in the Hollow brings pumpkins, costumes, trunk-or-treating, and one famously headless visitor

10:01 p.m. Oct. 6, 2026

Halloween in the Hollow Schedule

DUANE CROSS
MCO Publisher•Editor

Better keep your head about you Halloween night.

The Headless Horseman will make two trips through Lynchburg Square, and he won’t be the only strange thing wandering downtown.

Halloween in the Hollow returns Saturday, Oct. 31, with jack-o’-lanterns, trunk-or-treating, costume contests, music, and enough candy to keep Moore County dentists busy well into November.

The carving gets judged at 2 p.m. with the Jack-O-Lantern Contest at the gazebo.

Carved something frightening? Bring it. Made one that looks more confused than creepy? That works, too.

At 3:30 p.m., the Square closes to traffic while trunk-or-treat participants set up. First-, second-, and third-place awards are also on the schedule, so anybody decorating a trunk may want to give those plastic cobwebs a little extra attention.

Then comes the part the kids have been waiting for: trick-or-treating begins at 5 p.m.

By then, downtown should be crawling with witches, superheroes, skeletons, dinosaurs, and whatever costume somebody’s mama was still gluing together at 4:45.

Dressed to distress

The costume contests begin at 5:15 p.m., with divisions from Pre-K through adults, plus groups – including the grown-ups who insist the costume is “for the kids.”

First-, second-, and third-place prizes will be awarded in each division.

So if that vampire cape has been hanging in the closet since last October, this is its night. Just don’t get too comfortable. At 6:40 p.m., the Headless Horseman rides through the Hollow.

No word on where his head will be.

Time to boo-gie

Once the horseman clears the Square, the living get their turn. A dance party begins at 6:45 p.m. By then, somebody in an inflatable dinosaur suit will probably have found the beat.

The Headless Horseman returns for one final pass at 7:30 p.m.

After that, the Square begins to empty, the candy heads home, and parents get to find out exactly how much chocolate one child can eat before bedtime.

Just keep an eye out for the fellow on the horse. He’s already lost enough ...

October in Lynchburg

• Oct. 2 – Homecoming parade, ceremony, and varsity football game

• Oct. 3 – Whiskey Runners' Car Show

• Oct. 4-10 – National 4-H Week

• Oct. 8-10 – The Jack

• Oct. 10 – New Life Baptist Church Fall Festival

• Oct. 16 – The Lawn Sessions

• Oct. 17 – Rocktober on Whisky Hill

• Oct. 24 – Thunder in the Hollow

• Oct. 31 –Halloween in the Hollow

More Events

Thunder is coming to the Hollow

Thunder is coming to the Hollow

Bikes will roll into Lynchburg from every direction Oct. 24 for a day at Wiseman Park that will support the MCHS Marching Band.