Highlands turns date night into a full-on love story. Picture Main Street glowing after dark, crisp mountain air that makes everything feel a little more electric, and dinner reservations that are actually worth dressing up for. Start with a cheers, wander a bit, then settle in somewhere warm and candlelit where the only plan is to linger.
 

Valentine’s Day is sweet here, but the weekends on either side are the real “love hack.” Same romance, less rush. Make it a mini getaway: book a cozy hotel, claim your table for two, and let the rest be easy. One incredible meal, maybe a second round, and zero reason to check the clock.
 

HSC Date Night Dinner


Here are some of our favorite Date-Night Dining Options:
 

Date-night dining picks

  • Madison’s Restaurant – Elegant without feeling stiff, with the kind of glow that flatters everyone at the table. Valentine’s week brings chef-inspired touches, but any night here feels like a celebration.

  • Oak Steakhouse – A classic for a reason: candlelit warmth, polished service, and steaks that make an evening feel instantly elevated. Start at the bar, then settle in and let the night unfold.

  • Highlands Supper Club – Romantic and atmospheric, perfect for couples who love a proper night out. It’s the sort of place where you lean in closer, linger over courses, and order dessert because you’re not ready to leave.

  • Four65 Woodfire Bistro + Bar – Easy, lively, and made for sharing. Wood-fired pizzas, Italian-inspired plates, and a bustling bar set the tone for a fun, low-pressure date night.

  • The Ruffed Grouse Tavern – Moody, intimate, and quietly cool, with a chef-driven menu and a space that feels like a secret. Ideal for couples who want romance with a chic edge.

  • The Stubborn Bull – A spirited spot for couples who like their date nights with a little buzz and a lot of flavor. Expect craveable shareables, great cocktails, and a lively atmosphere that keeps the energy up long after dinner’s done.

Stubborn Bull

Valentine’s specials and sip-worthy happenings

  • The Vineyard at High Holly (nearby in Scaly Mountain): A ticketed Valentine’s wine dinner is on the calendar, plus seasonal stay offers.

  • Old Edwards Valentine’s Week (Feb 9–15): Dinner specials, themed cocktails, and a Champagne-and-strawberries moment for hotel guests, all designed for couples who want to make a whole weekend of it.

  • Highlands Supper Club (Feb 13–15): Valentine’s four-course prix fixe (Feb 13–14), plus a Valentine’s brunch (Feb 15).

  • Western Carolina Brew & Wine (Feb 14): “Love at First Flight,” complete with a photo booth and sweet pairings.

  • Oak Steakhouse (Feb 9): An intimate wine dinner featuring Davis Family Vineyards.

  • Mystery Dinner Theatre (Feb 13): A Valentine’s-themed whodunit with a catered dinner, plus wine and cocktails available for purchase.