Tucked into the Blue Ridge Mountains, Highlands is one of those places that feels much farther away than it actually is. Think winding mountain roads, waterfalls, cozy restaurants, boutique shopping, fireplaces, and a downtown made for wandering!
Highlands, North Carolina
Recommended: Friday–Sunday
Best Time to Go: Fall for foliage, winter for cozy weekends, or late spring/summer for hiking and patios.
FRIDAY | ARRIVE + DATE NIGHT
CHECK IN: HIGHLANDER MOUNTAIN HOUSE
Start the weekend at Highlander Mountain House. The historic inn feels more like a cozy mountain retreat than a traditional hotel, and its location puts you right near downtown Highlands.
Check in, drop your bags, and give yourself a little time to settle in before dinner.
WALK MAIN STREET
Head into downtown for your first look around. Browse the shops, wander Main Street, and get your bearings without trying to cram anything major into Friday night.
DINNER + DRINKS
Make Friday your proper date night. Highlands has surprisingly good dining for such a tiny mountain town, so this is one reservation I wouldn’t leave until the last minute.
Afterward, grab a cocktail or glass of wine at The Ruffed Grouse, conveniently location within the Highlander Mountain House!
THE WEEKEND LIST: Don’t schedule anything else Friday. The drive into Highlands is part of the experience, and this weekend should feel slow from the beginning.
SATURDAY | WATERFALLS + DOWNTOWN HIGHLANDS
Start slowly with coffee and breakfast at The Outpost Inn Coffee.
DRY FALLS
Then head to Dry Falls, one of the best stops near Highlands. A short trail takes you down to the waterfall—and you can actually walk behind it.
It’s a big payoff for very little hiking, which makes it perfect for a weekend when you want mountain scenery without spending half the day on a trail.
DRIVE THE MOUNTAIN ROADS
Instead of racing back downtown, take your time on the drive. Stop at overlooks, pull over when something catches your eye, and enjoy this part of the trip.
LUNCH + SHOPPING ON MAIN STREET
Head back into Highlands for lunch followed by a few hours downtown.
Browse the boutiques, home stores and local shops, grab another coffee if necessary (always necessary), and leave room in the schedule to just wander.
SATURDAY NIGHT DATE NIGHT
Head back to the hotel in the late afternoon, take your time getting ready, then make Saturday night the main date night of the weekend. Highlands has several restaurants that are worth planning the evening around.
For a classic romantic dinner: Ristorante Paoletti — An intimate Italian restaurant right on Main Street with a serious wine program. Reservations open 30 days ahead and are recommended.
For the special-occasion dinner: Madison’s Restaurant — Inside Old Edwards Inn, with seasonal Southern-inspired cooking and a more refined feel. After dinner, head upstairs to Hummingbird Lounge for a cocktail; the lounge currently has live entertainment on weekends.
WEEKEND LIST TIP: Make your Saturday dinner reservation when you book your stay, especially for fall and other peak weekends. Madison’s explicitly recommends reservations, while Paoletti accepts them up to 30 days in advance.
SUNDAY | SLOW MORNING + ONE LAST STOP
BREAKFAST + COFFEE
Sleep in, grab breakfast and take one last walk through downtown stopping at Mountain Fresh Grocery – grab something from the bakery, browse the prepared foods and local finds, or pick up a few things to bring home.
SUNSET ROCK
Before leaving Highlands, squeeze in one more mountain view.
Sunset Rock is a relatively short hike from town with a beautiful overlook across Highlands and the surrounding mountains. If you’re not feeling a hike Sunday morning, skip it without guilt and make the drive home leisurely instead.
Thanks for coming along! Whether you follow the whole itinerary or just steal a stop or two, we hope this makes planning your next weekend away a little easier. Save this guide for later, share it with your travel partner, and check back for more places worth adding to your list.
See you next weekend,
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