Highlands - Cashiers, North Carolina

Hikes (these are all medium difficulty or less)
Cashiers Area:
Whiteside Mountain is a must
Rainbow Falls at Gorges State park
Silver Run Falls (easiest)
Kings Creek Falls (just over the SC border)
Whitewater Falls overlook - very easy and the tallest falls east of the Mississippi.
Highlands:
Sunset Rock - very easy right outside of town and great view
Dry Falls - very easy, and very impressive
Bridal Veil Falls - you don't even get out of the car.
Secret Falls
Satulah Mountain - this one is actually more difficult. But the majority of the hike is on a neighborhood street. Great view at the end. You start this hike in downtown Highlands.

If you get a chance you can fly fish any number of rivers. Use Brookings Anglers in Cashiers and highlands as guides.

Other things:

There are hundreds of waterfalls in the area - more than I can list
Smokey Mountain National Park is an hour away.
Drive a section of the Blue Ridge Parkway

Lakeside, Paoletti's, and Wolfgang's are our favorites for dinner. On the Verandah can be good, but is a little inconsistent.

For breakfast, Mountain Fresh Grocery and Blue Bike Cafe. The latter gets crowded.

Ugly Dog for drinks and pub food. Food is just okay.

The brewery in Highlands is good - Satulah. The one in Cashier's was forgettable - Whiteside Mt Brewing.

Whiteside is much better from the standpoint of the location and ambience. Beer not so much

When are you going? If going on a weekend, do as much as you can early. The main attractions get really crowded as the day goes on. Places like Dry Falls, Whiteside Mountain, Glen Falls, etc. I've been to Dry Falls early on a Saturday morning, and had the place to myself. I've driven past it in the afternoon when you couldn't even get into the parking lot, and people waiting to turn into the parking lot were holding up traffic both ways. If you'll be there during the week, crowds are much more manageable. If you're into sunsets, pack a small cooler of beer/wine, and head up to Sunset Rock near sunset. It's a big exposed rock face that overlooks downtown, looking west. Weather permitting, you can see some stunning sunsets.

For shopping, downtown Highlands has a ton of different shops. Women in the group will love it. If the weather is nice, I don't mind walking around with the wife while she shops, but most of the shops are pretty boring - lot of clothing boutiques and home decor type places. There are a couple of bars downtown you can have a beer or two while she shops - Ugly Dog, Wild Thyme, Midpoint, and a couple of others. Satulah Mt Brewing is also downtown, though a couple of blocks off the main drag. Kilwin's has good ice cream to sit and eat while people watching.

I'm not as familiar with Cashiers. I do like the pizza place there - Slab Town. There is also an Ugly Dog there. Their shops seem a little more spread out.

We rented a house on Lake Glenville a few years ago.
High Falls, don't think it was in the lists above, is just north of Lake Glenville, which is just north of Cashiers. The trailhead is across the road from the Pines Recreation Area on the north shore.
It, I was told cause I didn't go, is a strenuous hike back up. Apparently you go down to see the falls. Rumor has it that there may be an easier trail now.
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There are two high falls in NC so if you google it be sure you check out the correct one.

Some of our group kayaked one day. The outfitter was east of Cashiers right on Hwy 64 I think but I don't know the name.
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