What's Happening in Moore County This Weekend: October 23-25, 2026 | Terry Nanney Real Estate Skip to content

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What's Happening in Moore County This Weekend: October 23-25, 2026

Terry Nanney By Terry Nanney · October 20, 2026 · 5 min read

Oktoberfest tents, pumpkins and string lights on the Village Green in Pinehurst at dusk

Halloween comes early across The Pines: BooFest trick-or-treating and a Toy Story 5 movie under the stars on Friday, the Village of Pinehurst's Oktoberfest and Kinderfest on Saturday, and a family-friendly Jekyll & Hyde, the Musical at BPAC all weekend.

It is the last full weekend before Halloween, and Moore County is going all in: BooFest trick-or-treating and a Toy Story 5 movie under the stars in downtown Southern Pines on Friday, the Village of Pinehurst's Oktoberfest and Kinderfest on Saturday, and a family-friendly Jekyll & Hyde, the Musical at BPAC on both Saturday night and Sunday afternoon. Add in live music, the Saturday farmers market, and the Scarecrow Stroll, and there is something for every age. Here is what's happening around The Pines from Friday, October 23 through Sunday, October 25:

Friday: BooFest and Toy Story 5 under the stars

Friday kicks off a weekend of early Halloween fun in downtown Southern Pines. Southern Pines BooFest runs from 5 to 8 p.m. and is made for kids 12 and under, with trick-or-treating along the sidewalks, games, and crafts in a safe, family-friendly setting at 145 SE Broad Street. Right after, grab a spot in Downtown Park for a free outdoor screening of Toy Story 5 from 6:30 to 8:30 p.m. Bring a blanket and a jacket; the evenings cool off quickly this time of year.

Earlier in the afternoon, the Southern Pines Public Library hosts The Big Boo! from 3:30 to 4:30 p.m., a kids' Halloween program that gets the little ones warmed up for the evening.

Brick storefronts of downtown Southern Pines glowing with string lights and pumpkins on a late-October evening
Downtown Southern Pines lights up for BooFest on Friday night

Friday night: Keller Williams at the Sunrise Theater

If you can get the kids settled and want a grown-up night out, Keller Williams brings his one-man band to the Sunrise Theater at 250 NW Broad Street in Southern Pines on Friday at 7:30 p.m. Known for his improvisational, loop-pedal performances that weave acoustic guitar with beatboxing and just about any genre you can name, he fills that intimate room with energy. Tickets are available through the Sunrise's box office and at sunrisetheater.com.

Heart & Soul plays the Pine Crest Inn

Over in the Village of Pinehurst, Heart & Soul brings live music to the historic Pine Crest Inn at 50 Dogwood Road on both Friday and Saturday nights, from 7:30 to 10:30 p.m. It is an easy, drop-in kind of evening in a classic Pinehurst setting.

Saturday: Oktoberfest and Kinderfest in the Village

Saturday afternoon and evening belong to the Village of Pinehurst's Oktoberfest and Kinderfest at James W. Tufts Memorial Park on the Village Green, 1 Village Green Road West. Kinderfest starts at 4 p.m. with kids' music, crafts, and a bubble artist, and Oktoberfest follows with oompah music, German food, and festive drinks running until 9 p.m. It is a lively, family-friendly way to spend a fall evening right in the heart of the Village.

Saturday morning: the Moore County Farmers Market

Start Saturday the right way at the Moore County Farmers Market in Downtown Park in Southern Pines, from 8 a.m. to noon at SE Broad Street and New York Avenue. You will find local produce, baked goods, and crafts from Sandhills growers and makers, with live music in the park to go with your coffee.

Scarecrow Fest at the Sandhills Horticultural Gardens

The free Sandhills Scarecrow Stroll continues at the Sandhills Horticultural Gardens, 3245 Airport Road in Pinehurst, with creative scarecrows tucked throughout the gardens from October 2 through November 1. This weekend is Scarecrow Fest, and Saturday brings a costume day and native plant sale, making it a perfect sunny-morning family outing before the Oktoberfest festivities begin.

A scarecrow in a straw hat standing among mums and asters at the Sandhills Horticultural Gardens
Scarecrow Fest at the Sandhills Horticultural Gardens

Jekyll & Hyde, the Musical at BPAC

This weekend, Imagine Youth Theater and Gary Taylor Dance bring Jekyll & Hyde, the Musical to BPAC's Owens Auditorium at 3395 Airport Road in Pinehurst, with performances Saturday at 7:30 p.m. and a Sunday matinee at 2 p.m. It is a big, theatrical take on the classic tale performed by local young artists, and a wonderful way to support the performing arts right here in the Sandhills. Tickets are available through Ticket Me Sandhills.

Saturday night, after dark

If you are still looking for plans after the family events wind down, the Knight Market takes over the Rec Room Bar + Arcade at 750 SW Broad Street in Southern Pines on Saturday from 7 p.m. to midnight: a dark-fantasy artisan market with vendors and a party atmosphere. And over in Pinehurst, Cocktails & Costumes, a costume fundraiser at The Fair Barn at 200 Beulah Hill Road, runs from 5 to 11 p.m. Saturday.

Get the full rundown

For the most complete list of what's happening across The Pines, I always point people to The Pines Times, which keeps an updated Moore County events calendar with details like tickets and times. You can find this weekend's listings there.

However you spend the weekend, I hope you get out and enjoy all Moore County has to offer. And if buying or selling a home in the Sandhills is on your mind, I'd love to help you find your place here.

Experience isn't expensive, it's priceless!

Terry Nanney, Realtor®

Towering Pines Real Estate, brokered by eXp Realty

Serving Moore County and the surrounding Sandhills of North Carolina

#MooreCountyNC #SouthernPinesNC #PinehurstNC #SandhillsNC #Oktoberfest #BooFest #ThingsToDoInMooreCounty #NorthCarolinaRealEstate #TerryNanneyRealtor

Written by

Terry Nanney

Terry Nanney

Local real estate agent in Southern Pines, NC, serving the wider Moore County Sandhills.

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