Highlands, NC Events by Month: A Year-Round Calendar

Highlands runs on a seasonal calendar. Summer brings chamber music, car shows and art fairs. September is packed with free festivals. October is all about color, and December belongs to the parade and the ice rink. This calendar lists events that recur each year, with the 2026 dates where they have been published. Dates move from year to year, so always confirm on the event’s own site or the Highlands Chamber of Commerce events calendar before you book.

Month by month

January

The quietest month. The ice rink at Kelsey-Hutchinson Founders Park stays open Thursday through Sunday, and Ski Sapphire Valley near Cashiers runs when the weather allows snowmaking. The Highlands Performing Arts Center shows live theater and performance broadcasts through the colder months. See our winter guide.

February

Skating continues through February 28. Ski Sapphire Valley hosts the Great Sapphire Outhouse Race, a long-running winter tradition. The 2026 race, the 19th, was held on February 7.

March

Late winter is slow, and some restaurants take a seasonal break. It is a good time for a quiet group retreat. If you plan to come back for summer shows, note that the PAC’s 2027 concert series goes on sale to the public on March 1, 2027.

April

Wildflowers start on the trails. The Highlands Plateau Audubon Society begins its spring field trips and bird walks. At month’s end the 3 River Fly Fishing Festival sends two-person teams out on three rivers over three days to raise money for the Town of Highlands Scholarship Fund. In 2026 it ran April 30 to May 2.

May

• High Style: A Chamber event held May 16 in 2026. Details are on the High Style page.
• Bear Shadow Music Festival: A three-day music festival from the Highlands Festivals team, held at Base Camp a few miles from downtown. The 2026 dates were May 29 to 31. See Bear Shadow.
• Audubon spring outings continue through the month.

June

• Highlands Motoring Festival: Four days and seven events for classic car fans, including a Main Street parade of classic cars and a judged show in Kelsey-Hutchinson Park. 2026 dates: June 11 to 14. See highlandsmotoringfestival.com.
• Mountaintop Art & Craft Show, first weekend: Two days of artists’ booths in Founders Park. 2026: June 27 and 28. See highlandsartshow.com.
• Chamber Music Festival opening gala: June 28, 2026, at the PAC.
• Summer weekly events start: the Saturday farmers market at Kelsey-Hutchinson Park (8 a.m. to noon in 2026), plus free evening concerts on Fridays on Main Street and Saturdays on Pine Street.

July

• Independence Day: Games at the ball field in the morning, a hot dog lunch from the Highlands Rotary Club, an evening concert at Kelsey-Hutchinson Founders Park, and fireworks after. Cashiers holds its own fireworks on the Village Green, which in 2026 were on July 3.
• Highlands-Cashiers Chamber Music Festival: Six weeks of concerts by visiting artists, alternating between the PAC in Highlands and the Village Green in Cashiers. The 2026 season, its 45th, ran July 5 to August 9.
• Highlands Biological Station: The station runs its Zahner Conservation Lecture Series and other nature programs in summer.

August

• Chamber Music Festival finale in early August.
• Highlands Twilight 5K: An evening race from Kelsey-Hutchinson Founders Park, run by the Rotary Club of Highlands. The next one is listed for August 21, 2027. See the race page.
• Mountaintop Art & Craft Show, second weekend: 2026: August 29 and 30.

September

The busiest month for free festivals. In 2026:

• Dazzling Dahlia Festival at The Bascom, September 10 to 12. Free, now in its 16th year. See thebascom.org.
• Highlands-Cashiers Film Festival, September 16 to 19, benefiting the PAC. See the festival site.
• Highlands Porchfest, September 20, 1 to 6 p.m. Free live music on porches and lawns around town, presented by the Center for Life Enrichment. See highlandsporchfest.com.
• Highlands Heritage Jamboree, September 26, at Kelsey-Hutchinson Founders Park. Free, with bluegrass, mountain and square dancing, and a moonshine display. See the Jamboree page.

October

Peak fall color, usually in mid-October. From mid-October to early November, the Shadow of the Bear appears below Rhodes Big View Overlook on clear evenings. On October 31, Main Street has traditionally closed to cars for Halloween on Main. The Bascom’s Holiday Market opens at month’s end. See our fall foliage guide.

November

The ice rink opens the week before Thanksgiving. The Saturday after Thanksgiving brings Small Business Saturday downtown and Light Up the Park & Main in the evening. The PAC usually has a holiday concert or two. Note that the Highlands Food & Wine Festival, held in mid-November for ten years, has been retired. It will not return in 2026.

December

The Highlands Christmas Parade fills Main Street on the first Saturday of December (December 5 in 2026). Santa visits the park on several Saturdays, and the rink stays open late over Christmas break and New Year’s Eve. See our Christmas in Highlands guide for the full holiday schedule.

How to plan a group trip around an event

• Book the house first. The weekends that fill fastest are mid-October, the Motoring Festival in June, July 4th, Thanksgiving and the parade weekend in December. For groups of 15 or more, reserving many months ahead is normal.
• Confirm the date before you book. Most events here move a few days each year. Check the event’s own site, not last year’s calendar.
• Buy tickets together. Chamber music concerts, PAC shows and Bear Shadow are ticketed. Buying for the whole group at once keeps everyone seated together.
• Use free events as the anchor. Porchfest, the Heritage Jamboree, July 4th and the Christmas parade cost nothing, so they work well for mixed-age groups where not everyone wants a ticketed show.
• Plan one group meal in. Restaurants are busiest on festival weekends. A catered dinner or private chef at the house takes the pressure off. See our catering and private chef guide.
• Add a shoulder day. Arrive Thursday instead of Friday. You get one quiet day on the trails before the crowds come in.

Planning a reunion, wedding or retreat around one of these weekends? Our group trips guide covers logistics, and Fairview House sleeps up to 22 four blocks from Main Street.