Romantic Things to Do in Highlands, Cashiers, and Franklin, NC
Looking for romantic things to do in Highlands, NC, or the towns around it? This guide focuses on places rather than dates. Vineyard dinners, tasting menus, hands-on cooking classes, and quiet bookstore evenings run all year on the Highlands-Cashiers plateau and down the mountain in Franklin. Each February, the same venues put out Valentine's menus and workshops, usually announced in January.
Why This Guide Lists Places, Not Dates
Event roundups go stale within weeks. Plateau businesses post Valentine's dinners, classes, and library programs a few weeks ahead, and those seats sell out fast. Rather than publish dates that expire, this guide covers the venues worth watching and where their current schedules appear. For Franklin and Macon County, Experience Franklin tracks downtown businesses and happenings. For library programs in Cashiers, Highlands, Franklin, and Bryson City, the Fontana Regional Library events calendar carries the whole system. The Highlands Chamber of Commerce and the Cashiers Area Chamber of Commerce also publish seasonal calendars.
Things to Do in Highlands for Couples: Wine and a Long Dinner
The Vineyard at High Holly sits on Scaly Mountain, between Highlands and Dillard, Georgia, on roughly 30 acres of working vineyard. There is a tasting room, a full bar, walking trails, a pond, and a dahlia garden, plus luxury cottages if you would rather not drive the mountain at night. Its restaurant, Barrel and Vine, pours wine by the glass, bottle, and flight, and the vineyard hosts themed dinners, live music, and artist-led workshops year-round. Check its calendar for open hours before you go.
In Highlands itself, Roots and Vine is a tasting-menu-only restaurant built around Appalachian sourcing, with courses that change through the season and optional wine pairings. It is the plateau's version of a long, slow dinner: you choose among options on several courses and the kitchen sets the rest. Reserve well ahead, and if you want more options, our guide to restaurants in Highlands and Cashiers and our local dining guide cover the rest.
Things to Do in Cashiers, NC: Cook Together
The Barn, in Glenville just north of Cashiers past Lake Glenville, has been running hands-on cooking classes in a restored family barn for close to a decade. Groups are small; the class runs about four hours, three of them in the kitchen, and it ends with a seated meal of what you cooked. The Barn lists private group classes at $245 per person for 2026, wine and wine education included, and describes itself as a good fit for couples who want to learn a skill together. Owner Kristin Jorgensen also runs La Poste, a natural wine and cook shop with a teaching kitchen in downtown Cashiers on NC 107, in a building that served as the town's first post office in 1897.
Classes book out in the busy season, so ask early. For a couple weighing a move to the plateau, a winter class is also a good way to see how the area feels when the summer crowd is gone; our Highlands versus Cashiers comparison covers the rest.
Things to Do in Franklin, NC on a Date Night
Franklin is about half an hour down US 64 from Highlands and makes an easy, unfussy date. Gracious Plates on Main at 46 East Main Street serves farm-to-table plates sourced from local farms, with a wine list, cocktails, and a covered Main Street patio. The restaurant has also run guest-sommelier wine tastings on Wednesday evenings; confirm the current schedule when you call.
A few doors down, A Novel Escape at 60 East Main Street stocks more than 14,000 new and used books along with puzzles, cards, and gifts, and it hosts book clubs on the first and third Thursdays of the month. Dinner, a browse, and a walk along Main Street is a complete evening that costs the price of a meal.
Free and Low-Cost Dates
The Albert Carlton-Cashiers Community Library, a Fontana Regional Library branch on Frank Allen Road in Cashiers, runs free programs for adults year-round, from author events and guest speakers to craft and art sessions. Its community space has hosted workshops that pair well with a Valentine's Week outing, and attendance is free.
Outdoors, the plateau's waterfalls are a good short date in any season, and several sit within a few minutes of US 64. Our guide to Cashiers waterfalls maps the reliable ones. In town, walkable Highlands means you can park once, have dinner, and browse the shops on foot.
Planning a Winter Date in the Mountains
Winter changes the logistics more than the options. Hours thin out after the fall season, and some plateau businesses close early in the week or for part of the winter, so confirm before you drive. Reserve any Valentine's menu or class as soon as dates post in January, since the dining rooms and class tables here are small. Allow extra driving time on the Highlands-Cashiers stretch of US 64 and on the Highlands-Franklin descent, both of which are curvy and hold ice in shaded curves. If the forecast turns, a cottage or vacation rental nearby beats a late drive home.
What This Means If You Are Thinking About Buying Here
A February visit tells you something a July visit cannot. Which restaurants stay open, how the roads handle weather, how quiet the village gets, and how far you would drive for dinner in the off-season all matter to anyone considering a move or a second home. Buyers who love the plateau in summer sometimes find the winter version either better or harder than they expected, and that is worth learning before you commit.
If you are weighing it, walk the towns in both seasons. Our pages for Highlands, Cashiers, and Franklin lay out what each market offers; choosing a second home covers the questions a part-time buyer should settle first, and our listing search shows what is available now.
Where to Check Current Dates
For dinners and classes, go to the venue's own site or social account; that is where Valentine's menus and class seats appear first. For library programs, use the Fontana Regional Library calendar. For Franklin, Experience Franklin and the Franklin Chamber of Commerce list downtown happenings. For Highlands and Cashiers, the Highlands Chamber of Commerce and the Cashiers Area Chamber of Commerce keep seasonal calendars, and our own Highlands events page tracks what we hear about locally.
Frequently Asked Questions
What are romantic things to do in Highlands, NC?
Dinner at a tasting-menu restaurant, an afternoon at a nearby vineyard, a walk through the shops and galleries downtown, and a waterfall drive are the standbys. In winter, add a cooking class near Cashiers or an evening wine-shop tasting. Reserve ahead; the plateau's dining rooms are small.
Is there a winery near Highlands, NC?
Yes. The Vineyard at High Holly is a working vineyard on Scaly Mountain, between Highlands and Dillard, Georgia. It has a tasting room, a full bar, an on-site restaurant called Barrel and Vine, walking trails, and luxury cottages, and it hosts themed dinners, live music, and workshops year-round.
Where can you take a cooking class near Cashiers, NC?
The Barn, in Glenville just north of Cashiers, has run hands-on cooking classes for nearly a decade in a restored family barn. Classes are small and end with a shared meal of what the group cooked. The same owner runs La Poste, a natural wine and cook shop with a teaching space in downtown Cashiers.
What is there to do in Franklin, NC on a date?
Downtown Franklin is a compact evening: dinner on Main Street, a browse through the bookstore, and a walk along the sidewalks and the Little Tennessee River greenway. Gracious Plates on Main serves farm-to-table plates with a full wine list, and A Novel Escape stocks new and used books a few doors away.
Are Highlands and Cashiers restaurants open in winter?
Some are, but hours thin out after the fall season and several plateau businesses close early in the week or shut for part of the winter. Always call or check the venue's site before you drive up for a winter dinner, and have a second choice in mind.
When are Valentine's Day events announced on the Highlands-Cashiers plateau?
Most Valentine's dinners, classes, and library programs are announced in January, a few weeks ahead. Restaurant prix-fixe menus and cooking classes usually sell out quickly, so watch venue websites and social accounts in early January and book as soon as dates post.
How far is Highlands from Cashiers, NC?
Cashiers sits about 25 to 30 minutes east of Highlands on US 64, at the junction with NC 107. Franklin is roughly a half hour down the mountain from Highlands on US 64 west. Allow extra time in winter; the Highlands-Cashiers stretch is curvy and can hold ice in shaded curves.
You May Be Interested In
Best Restaurants in Highlands and Cashiers: where to eat beyond a special occasion.
Cashiers NC Waterfalls: a local's guide to the plateau's cascades.
Highlands vs. Cashiers: seven factors that decide where buyers land.
Highlands, NC Real Estate: neighborhoods, price bands, and what is for sale.
Highlands Events: what is coming up on the plateau.
Fontana Regional Library: free programs in Cashiers, Highlands, Franklin, and Bryson City.
The best romantic things to do in Highlands, NC are the ones you can repeat: a vineyard afternoon, a long dinner, a class you cook through together. If a February visit has you thinking about staying, contact Vignette Realty in Franklin or Highlands.
Disclosure: Details change; confirm hours, prices, and dates with each business before you go. Vignette Realty is a real estate brokerage with offices in Franklin and Highlands, North Carolina. It has no financial interest in and receives no compensation from any business named in this article.
Equal Housing Opportunity.
