Planning a Group Trip to Highlands, NC: Reunions, Weddings and Retreats

A trip for 10 to 22 people runs on logistics. Who drives with whom, who cooks Tuesday, which dinner needs a reservation in March. Highlands works well for groups because the town is small and walkable, and most of the outdoor highlights are within 20 minutes. This guide covers the planning that makes the week easy.

Pick the right kind of trip

Family reunions

Plan around the youngest and oldest in the group. Choose one easy outing a day that everyone can do, such as Sunset Rock, the Botanical Garden or the short paved path at Dry Falls, then let the energetic half add a bigger hike. Leave one full day unscheduled.

Wedding weekends

Keeping the wedding party under one roof makes the weekend calmer. Getting ready, rehearsal dinner leftovers and the morning-after brunch all happen in one place, and nobody has to drive between inns. A few legal basics for North Carolina:

• Get your marriage license from the Register of Deeds in any North Carolina county. It is valid for 60 days, and there is no waiting period.
• The officiant must be an ordained or church-authorized minister or a magistrate. Judges cannot perform weddings in North Carolina.
• Two witnesses must sign the license after the ceremony.

Confirm details with the North Carolina Judicial Branch and the county Register of Deeds before you go.

Corporate retreats

Mornings for work, afternoons outside. Whiteside Mountain or a guided fly-fishing trip makes a good team outing, and a private chef keeps dinners in-house where people can actually talk. Plan for spotty cell coverage on trails and in the gorges, and make sure the house Wi-Fi meets your needs before you book.

Reservations to make early

Few downtown restaurants can seat 20 together on a busy night. Ask about private rooms, split into two tables at nearby times, or bring the dinner home.

Meals for a crowd

Plan a mix: one or two nights out, a catered or chef-cooked dinner for the big night, and simple home meals the rest of the week. Shop before you arrive. Bryson’s Food Store in town covers the basics, and the larger Ingles in Cashiers is about 25 minutes away. Assign each household one dinner and one breakfast so nobody spends the week in the kitchen. See groceries, private chefs and catering and where to eat.

Cars and getting around

• Plan on one car per four or five people for day trips. Mountain roads and trailhead lots favor fewer, fuller cars.
• Trailheads like Glen Falls, Whiteside Mountain and Dry Falls have limited parking. Carpool and go early.
• If you stay near downtown, walk to dinner and leave the cars parked.
• Airport runs add up. Coordinate arrivals into Asheville, Greenville-Spartanburg or Atlanta so drivers can share trips. See getting to Highlands.

Activities that split and regroup well

Pick a meeting point and a time, not a plan for every hour. More ideas in things to do and family adventures.

Practical details

• Medical: Highlands-Cashiers Hospital at 190 Hospital Drive has a 24-hour emergency department.
• Weather: Pack layers and rain gear for everyone. Evenings are cool even in July.
• Accessibility: Dry Falls has an accessible viewing platform. The Highlands Chamber publishes an Accessible Highlands guide.
• Events: Check the events calendar. A festival weekend can be a bonus or a parking headache.

Where to stay as one group

Large houses that sleep 20 or more are rare in Highlands, so start looking early. Fairview House is a restored 1910 estate four blocks from Main Street with 10 bedrooms, 8 of them en-suite, and room for 22 guests overnight. It hosts events of up to 22 guests and offers day rates for photo shoots, and the Highlands Performing Arts Center is across the street.