Spring (March, April, May)
- Southern Pines Garden Club House & Garden Tour – TBA
- IHRA Spring Nationals Drag Racing – TBA
- Southern Pines Horse Trials Combined Driving Event – TBA
- Hunter Jumper Trials – March
- 7th Annual Camellia Festival – March
- Midland Crafter’s Day – March
- Renaissance Fair in Raleigh – March–April
- Pinehurst Harness Track Matinee Races – April
- Springfest & Tour de Moore International Bicycle Race – April
- Seagrove Spring Kiln Opening – April
- Stoneybrook Steeplechase – April
- Moore County Relay for Life – April
- 12th Annual Run for the Roses Wine Tasting – May
- Cameron Spring Antiques Street Fair – May
- Carthage Buggy Festival – May
- Seven Lakes 7K & May Follies – May
- Young Eagles Day Free Plane Rides at Moore County Airport – May
- Sunday Polo at Pinehurst Mile Track – April–May
- Rooster’s Wife Concert Series – May–September
- First Fridays in downtown Southern Pines – April–October
Summer (June, July, August)
- North & South Amateur Golf Tournaments – TBA
- Sam Ragan Annual Poetry Festival – June
- Independence Day Celebrations & Fireworks – July
- Annual Carthage 4th of July Parade
- 45th Annual 4th of July Celebration in Aberdeen
- Annual Pet Parade in downtown Pinehurst
- Fireworks at the Fair Barn
- 67th Annual Pinehurst Junior Tennis Classic – July
- Sunrise Blues Crawl, downtown Southern Pines – July
- Summerfest Street Fair – July
- US Kids Golf World Championship – July
- Annual North Carolina Peach Festival in Candor – July
- Robbins Farmers Day Festival – August
- USTA National Men’s 70-85 Clay Court Championship – August
- Outdoor Jazz Band Concerts – June to August
- Fine Arts Festival – June–August
- Rooster’s Wife Concert Series – May–September
- First Fridays in Downtown Southern Pines – April–October
Fall (September, October, November)
- IHRA Fall Nationals Drag Race – TBA
- 20th Annual Labor Day Wine Festival – September
- Kitchen and Moore Home Tour – September
- 41st Annual Malcolm Blue Farm Craft & Farm Skills Days – September
- NAMI 3rd Annual Pathway to Awareness Weekend – September
- 18th Annual Sardine Festival – October
- 8th Annual Candor Bluegrass Festival – October
- First Fridays in downtown Southern Pines – April–October
- Moore County Agricultural Fair – October
- Various Fall Festivals at local schools and churches – October
- Midland Crafter’s Day – October
- Autumnfest Street Fair – October
- Cameron Fall Antiques Street Fair – October
- Holly Arts & Crafts Festival – October
- NC State Agricultural Fair in Raleigh – October
- Blessing of Moore County Hounds & Opening of Hunt Season – November
- 50th Annual Antiques Show & Sale – November
- 29th Annual Seagrove Pottery Festival – November
- NC Symphony Holiday Pops Concert – November
- Festival of Trees and Lights – November
- Sunday Polo at Pinehurst Mile Track – September – November
Winter (December, January, February)
- 4nd Annual Reindeer Run – December
- Weymouth Center Christmas House Tour – December
- Annual Christmas lightings and celebrations throughout the Sandhills – December
- 33rd Annual Candlelight Tour of Homes – December
- 16th Annual Seagrove Potter’s Christmas Open House – December
- Terpsichore’s annual performance of the Nutcracker – December
- Christmas Horse Carriage Drive – December
- Moore County Choral Society Christmas Concert –December
- Donald Ross Junior Golf Championship Tournament – December
- First Eve in downtown Southern Pines – December 31
- Dreams of Enchantment Light Event – December – January
- MOPS Guest Speaker Series – January
- 5th Annual Spelling Bee for Literacy – January – February
- North Carolina Barbershop Harmony Brigade – January