There’s a reason people plan entire weekends around being in Highlands in October. The weather cools down, the leaves start changing, and suddenly a drive you’ve made a dozen times takes twice as long because everyone in the car wants to stop and look at the view.
I’ve photographed quite a few Highlands, North Carolina weddings over the years, and I love when couples want their guests to experience this place beyond the events they have planned. Especially in the fall. You have people you love coming into town, sometimes from all over the country, and you want them to understand why you chose Highlands in the first place.
Thankfully, finding things to do in Highlands, North Carolina in fall is pretty easy. You can spend the morning hiking, wander downtown in the afternoon, drive over to Cashiers, have an incredible dinner, and still have plenty of time to get back and get ready for whatever is happening that evening.
So if you’re putting together recommendations for your guests or planning a few extra days around a Highlands NC wedding weekend, these are some of the places and activities I’d send you to first.
And if you’ll be here earlier in the year, I have a whole guide to things to do in Highlands in the spring, too.
See the fall colors in Highlands, NC
The Highlands NC fall colors are obviously one of the biggest reasons people head this way during October, and you really don’t have to work very hard to find them.
Highlands sits at 4,118 feet, so the leaves typically begin changing earlier here than they do at lower elevations nearby. Peak color is usually sometime in October, with the exact timing changing every year depending on the weather and elevation. That also means you can drive from Highlands toward Cashiers or down into the gorge and see completely different stages of fall color along the way.
If seeing the fall foliage in Highlands NC is high on your list, keep an eye on local foliage updates as your trip gets closer. And give yourself more time than you think you’ll need to get places. October is popular in Highlands for a reason, and traffic tends to pick up along with the color.
Go hiking in Highlands, NC
If I were putting together a fall weekend in Highlands, I’d absolutely make time to get outside. Hiking in Highlands NC can mean anything from an easy walk with a view to spending a few hours on the trail, so your guests can choose something that feels doable for them.
Whiteside Mountain
Whiteside Mountain is one of the first places I’d recommend. It’s located between Highlands and Cashiers, so it’s easy to work into a morning that includes both towns.
The loop is about two miles, and you get some incredible views from the top. In October, when all of those ridgelines are covered in fall color, it’s even better.
This one gets busy during leaf season, so I’d plan on going earlier in the day, especially on a weekend. Give yourself time for the hike, the views, and all the photos your group is inevitably going to take once you get up there.
Sunset Rock
Sunset Rock is another favorite because it’s so close to downtown Highlands NC. You can grab coffee, walk around town for a little bit, and head up later in the afternoon for the view.
The walk starts near downtown and takes you up to a wide overlook above Highlands. I’d check the sunset time before you go, wear shoes you’re comfortable walking in, and bring an extra layer because the temperature can change pretty quickly once the sun starts going down.
This is also an easy recommendation for guests who want to spend some time outside without committing half of their day to a hike.
Spend a morning chasing waterfalls
There are plenty of waterfalls near Highlands NC, and several are easy to visit without planning a full hike.
Dry Falls is one of the best-known stops along US 64 toward Franklin. A walkway takes you behind the waterfall, which makes it especially fun if you have kids with you or guests who haven’t spent much time in this part of North Carolina. Bridal Veil Falls is nearby and can easily be added to the same drive (also, the name alone makes this a fun site-seeing activity during your wedding weekend!).
If you’re heading toward Cashiers, Silver Run Falls is another easy stop to add to the day.
I’d choose one or two and give yourself time to enjoy wherever you are.
Take a drive just to see the leaves
One of my fall recommendations: get in the car and just… drive.
Some of my favorite views around Highlands are the ones you come across when you’re driving from one place to another.
Drive through the Cullasaja River Gorge
Take US 64 west from Highlands toward Franklin and you’ll wind through the Cullasaja River Gorge with mountain views, waterfalls, and plenty of fall color along the way. Bridal Veil Falls and Dry Falls are both along this route, so you can easily combine a scenic drive with a few stops.
The road gets narrow and curvy in places, so take your time. I’d also go earlier in the day during October when there are fewer cars on the road and you can enjoy the drive without feeling rushed.
Head toward Dillard
NC 106 toward Dillard, Georgia is another beautiful fall drive, and there are overlooks along the way where you can pull over and take everything in. Blue Valley Overlook is only a few miles outside downtown Highlands, with Osage Overlook a little farther down the road.
This is a good option for guests who want the mountain views and fall color without spending the morning on a trail.
Drive toward Cashiers and see the Shadow of the Bear
If you’re in Highlands from around mid-October into early November, you may also be able to catch the Shadow of the Bear.
Around sunset on clear fall days, Whiteside Mountain casts a shadow over the valley that looks like a bear. You can see it from Rhodes Big View Overlook on US 64 between Highlands and Cashiers. It only appears for a short window, and plenty of people come out hoping to see it, so give yourself extra time and be careful around the overlook and highway.
It’s one of those very Highlands things that’s fun to put on a wedding weekend recommendation list because most out-of-town guests have probably never heard of it.
Spend an afternoon in downtown Highlands, NC
I love that you can give guests an open afternoon in downtown Highlands NC without having to give them much of an itinerary. Downtown is compact and walkable, so people can shop, grab something to eat, meet up for a drink, and make their own plans from there.
Main Street has plenty of local shops to wander through, including Highland Hiker, and there are lots of places nearby to stop for coffee or something sweet. Mountain Fresh Grocery is also one of those places that works for just about everybody, whether they want breakfast, lunch, pizza, coffee, or something to take with them for later.
The Bascom is another spot worth adding to your list. It’s a visual arts center just outside downtown with rotating exhibitions, and it’s especially helpful to keep in mind if the weather changes and you need something indoors.
For a wedding weekend, I’d leave a Friday afternoon fairly open and give guests a few of these recommendations. Some will shop. Some will eat. Some will end up sitting somewhere talking for two hours. All of those sound like a pretty great way to spend an afternoon before the weekend really gets going.
Drive over to Cashiers for the morning
If you’re looking for things to do in Cashiers, NC during your stay, start by giving yourself a morning to explore. Cashiers is only about ten miles from Highlands, and the drive between the two is especially pretty in October. If your guests are staying for a few days, it’s an easy way for them to see a little more of this part of western North Carolina.
The Village Green sits in the center of Cashiers and has walking paths, gardens, outdoor art, and plenty of space to wander around. If your trip overlaps with one of its seasonal events, check the calendar before you go.
Cashiers also has plenty of shopping, especially if your people love home goods, antiques, and local finds. The Cashiers Farmers Market is another fun stop if you’re looking for snacks, local goods, or a few things to bring back to wherever you’re staying.
You could easily spend the morning here, have lunch, and be back in Highlands with plenty of time to get ready for an evening event.
Eat your way through Highlands and Cashiers
This might be my favorite recommendation on the list. There are so many good restaurants in Highlands NC, and if you’re already bringing your favorite people to the mountains for a wedding, you might as well feed them well, too.
For a nicer dinner, Madison’s at Old Edwards Inn and Ristorante Paoletti are all worth looking into. Reservations can fill quickly during fall, so this is something I’d plan ahead for, especially with a larger group.
Mountain Fresh Grocery is great for something more casual, and Wild Thyme Gourmet is another longtime Highlands favorite. The Hummingbird Lounge at Old Edwards is also a fun place to keep in mind for drinks later in the evening.
Over in Cashiers, Cornucopia is great for lunch, and Whiteside Brewing Company works well for a casual group. Canyon Kitchen at Lonesome Valley is another beautiful option for dinner if it’s open during your dates.
For couples planning their wedding weekend, food is also one of the easiest ways to give each part of the weekend its own feel. A rehearsal dinner, welcome party, Saturday lunch, and Sunday brunch can all give your people another chance to spend time together. Those are usually the parts of a wedding weekend where I see people settle in, catch up, and get to know each other before or after the larger celebration.
A few things I’d keep in mind for a fall wedding weekend
October is a busy time in Highlands, so I’d make reservations and book accommodations earlier than you think you need to. The same goes for anything your guests will need to reserve ahead of time, including spa appointments and larger dinner reservations.
I’d also tell everyone to pack layers. Highlands sits above 4,000 feet, and temperatures can change quickly once the sun goes down. If you have outdoor events planned, wraps, jackets, or blankets can make everyone a lot more comfortable later in the evening.
The earlier sunset is important to consider for your photography timeline, too. Fall wedding weekend timelines usually need to account for that earlier light, especially if portraits or an outdoor ceremony are part of the plan. Your planner and photographer can work through those details with you well before the weekend so everything has the time it needs.
And please give your people some free time.
You don’t have to fill every hour of the weekend for everyone to have a great experience. Give them a few recommendations, tell them what you love about Highlands, and leave room for them to make the weekend their own. Some of the best time together happens over a long lunch, on a drive through the mountains, or back at the hotel when nobody has anywhere they need to be for a few hours.
Why I love photographing fall wedding weekends in Highlands
As a Highlands, NC wedding photographer, I’ve photographed enough celebrations here to know how special it is when couples bring all of their people to the mountains for more than a single event.
There’s the rehearsal dinner where families start settling in together, the welcome party where you finally get to hug the friends you haven’t seen in months, the wedding itself, and the brunch the next morning when everyone is tired and happy and telling stories from the night before.
That’s why I love photographing the whole weekend. I get to know your people. They get used to having me around. And by the time the wedding starts, I already know who your college roommate is, which grandparent everyone keeps checking on, and which friend is probably going to be the first one on the dance floor.
If you want to see what that can look like, spend some time with Meredith and JG’s Highlands wedding weekend, including their farewell brunch at Piermont Cottage. You can also look through Meredith and Marc’s wedding at The Farm at Old Edwards, which I photographed here in Highlands in October.
A quick note about The Farm at Old Edwards (August 2026): The Farm recently experienced an unexpected fire and is currently unavailable. I’m leaving this wedding linked here because The Farm has been such a special part of so many Highlands celebrations, including ones I’ve had the privilege of photographing. I’ll update this post as Old Edwards shares more information about what comes next.
I also have a guide to Highlands wedding venues if you’re still deciding where you want to celebrate, along with my guide to the best East Coast wedding venues for a destination weekend if Highlands is one of a few places you’re considering.
And if you already know Highlands is where you want everyone you love to gather, I’d love to hear what you’re planning.
