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With the amount of times I’ve been to Highlands (starting all the way back in this blog post from 2014), I cannot believe I haven’t written a Travel Guide yet! Highlands is such a special place, for so many reasons. Chris and I spent an anniversary there many years ago and I’ve been back numerous times with my family and my dog Winnie. It’s outdoorsy and posh all at the same time, with lots of local and fresh eateries, an award-winning spa, amazing wine and much, much more. If you have a four-legged friend, then you’re also in luck, because Highlands is incredibly dog-friendly!

I’m rounding up the outfits I wore first, but continue on for the full travel guide at the bottom of this post.

This photo was taken at a local produce stand just a few miles from downtown! We bought local cheese, apple cider and fresh berries. Outfit details: off-the-shoulder sweater (only $17!) // Good American jeans // similar hat // similar Chanel boy bag // similar leopard mules

leopard sweater // ripped jeans // suede heels // similar hat

The best coffee shop: Buck’s! I love their apple cider. Outfit details: checkered poncho // black dress // similar Chanel boy bag

Everywhere you look, a cute porch to relax and enjoy the outdoors! Outfit details: buffalo check fleece // leggings // UGG boots

Taken outside of Buck’s (back for another apple cider!). Outfit details: cashmere scarf // white tee // similar leggings // Converse shoes

Where to Stay

PARK ON MAIN: This is our favorite hotel to stay at in Highlands, for several reasons, but the first being it’s an entire hotel centered around DOGS! There are dog portraits all over the walls and they really cater to your pet, providing a dog bed, blanket, dog toy, food bowl, etc. when you check in to your room. If you don’t want to bring your furry friend, have no fear – the rooms are so clean you would never even know a dog had been there before. Other reasons we adore this hotel: it’s much more affordable than Old Edwards Inn, and they provide a complimentary breakfast in the lobby each morning! I really enjoyed putting on my cozy fleece and UGGs to go down for coffee and breakfast every morning (because in the mornings it’s so much cooler in September). The hotel is small and there’s a gorgeous courtyard in the center with lots of flowers and little tables and chairs where you can hang out and eat cheese and enjoy a glass of wine.

OLD EDWARDS INN: Old Edwards is THE hot spot in Highlands. I’ve stayed there a bunch of times and do really love it – it is expensive, though, and dogs are not allowed anywhere on the property (just a note if you’re a dog owner!). It really is beautiful though – it reminds me of a European mountain resort with a gorgeous historic inn, beautiful stone guest cottages and more fireplaces than you can count. Everywhere you look, there’s a nook or cranny where you could curl up with a good book! Old Edwards is incredibly romantic and I would highly recommend staying here for an anniversary.

Where to Eat and Drink

BREAKFAST/LUNCH

MOUNTAIN FRESH GROCERY: We love this little spot for breakfast and lunch! It’s basically a grocery store with a little restaurant inside where you can order food, hang out and eat, and also pick up some snacks for your hotel room or cabin. They have a vast wine selection, as well as a ton of different fresh cheese options to grab and go for later, and a little bakery that makes THE BEST pumpkin bread. The restaurant Mountain Fresh Pizza is connected to Mountain Fresh Grocery and we enjoyed the pizza there, too.

BUCK’S COFFEE: This coffee shop is around a 15 minute drive from Highlands, located in Cashier’s, but it’s worth it to go because I love the vibe of this coffee shop so much! There are antlers on the walls, a huge fireplace in the middle and lots of comfortable leather chairs distributed around the shop. I like their coffee but the real winner is their hot apple cider. They also have sandwiches and paninis to-go, which would be great to grab before a hike!

PIZZA PLACE OF HIGHLANDS: If you aren’t looking for this pizza shop, it’s easy to miss! Tucked away on Main Street, this pizza place is without a doubt the best pizza in Highlands. My husband and I constantly reminisce on our favorite pizza there, the Jalapeno Popper Pizza. Yep, you heard that right. Smothered in cheese and cream cheese and topped with bacon and jalapenos, you won’t have a better pizza in your life.

DRINKS

HIGHLANDS WINE SHOPPE: This cute little wine shop is located right across the street from Park on Main. They have a HUGE selection of wine and you can go in and pick out a bottle to-go, or sit on the front lawn and drink a glass right there. It’s a really nice place to spend the afternoon!

THE WINE GARDEN: This little “wine garden” is located inside Old Edward’s Inn next to Madison’s. The ambiance here is so calming – you’re surrounded by lush greenery, market umbrellas and there’s even a small patio-side waterfall. They do have a really good lunch menu, but I personally prefer to order a cheese plate and sip on some rosé on a nice afternoon.

UGLY DOG PUB: This is the cutest little pub! It’s a great place to go to watch a game (I’m pretty sure Chris dragged me here for a Clemson game one time) and they have a wide selection of regional beers and uniquely crafted cocktails.

DINNER

RISTORANTE PAOLETTI: This is our favorite restaurant in Highlands!! A lot of the restaurants are considered “fine dining” and are on the expensive side, so maybe save this one for a special occasion? It’s a very romantic Italian restaurant with some of the finest food around. I’ve had the gnocchi and the wild-caught grouper (both of which are amazing), my dad swears by their spaghetti, and we always, always splurge on dessert afterward. Their creme brulee is amazing and we also order a few scoops of gelato, along with some decaf coffee. We really go all out for this one, y’all!

WILD THYME: We tried out Wild Thyme for the first time a few weeks ago and my whole family is now obsessed with it. They have an incredible menu and every single thing we got there was delicious. Plus, you can sit outside and bring your pup, and Kilwin’s ice cream and fudge shop is right next door!

MADISON’S: Madison’s is a staple in Highlands, as it’s the farm-to-table restaurant at Old Edward’s Inn (and it’s also expensive, just to note). I love that the chefs create their menu from sustainable ingredients from their own gardens! If you do book a stay at Old Edward’s Inn, you get a special deal for a three-course meal at Madison’s and you should definitely take advantage of it!

BISTRO ON MAIN: We love sitting outside on the patio at Bistro on Main and always go at least twice during our trip to Highlands – once for lunch and once for dinner. Their pimento cheese fritters give me LIFE, along with their salads, tomato soup and their shrimp-stuffed salmon. On the weekends they have live music!

What to Do

RELAX!: Highlands was basically built for relaxing. Whether it’s curled up next to a fireplace with a good book or sipping a glass of wine and munching on a cheese plate on a patio, people travel here from all over just to soak up the fresh mountain air and the slow lifestyle.

THE SPA AT OLD EDWARD’S: On the same topic of relaxation, this spa is an absolute must if you come to Highlands. Rated Condé Nast’s Top Hotel Spa in North America, the Spa at Old Edwards is one of the best spa experiences I’ve EVER had (and I’ve been to a lot of spas!). I like to check in an hour early to get the most out of my spa day (and always bring along a book!). Let me walk you through the experience: after check-in, you’re led to a gorgeous locker room where you can change into one of Old Edward’s fluffy robes and a pair of slippers. From there, I head to the main room and fill up a mug of hot chamomile tea, adding in some local wildflower honey to sweeten the taste. Then I curl up by the fire with my book, or head to the solarium to rest on one of the comfy chairs and listen to the sound of nature. When it’s time for the appointment, the massage therapist calls my name and we head back to a private treatment room in the Spa Suite. All of their skin treatments and massages use herbs and botanicals from their own gardens and are beyond magical. Afterward, I may grab a bite to eat or a glass of wine in their spa cafe, head to the jacuzzi tub, or take a quick shower using their luxurious bath products. They even leave out razors and hair brushes for you to use! It truly is a one-of-a-kind experience.

WINDOW SHOP: The town itself is really fun to walk around, as there are a ton of boutiques and little antique shops that you can peruse. Grab a hot coffee and put on your walking shoes to cruise around town – our favorite is the vintage jewelry shop and checking out all the estate jewelry!

HIKE: There are several hikes and waterfalls surrounding Highlands. Bridal Veil Falls is located on US 64 west just two and a half miles from downtown Highlands. You can park and stroll behind the gentle cascade. Or try Dry Falls – it’s a mile past Bridal Veil – and you can walk behind this 75-foot deluge while remaining mostly dry (hence the name!). Sunset Rock is another good one – it’s an easy 1.2 mile round trip hike and offers breathtaking views of the sunset over Highlands.

What to Pack

No matter what time of year you go, prepare for cooler weather! Highlands is unique and since it has such a high elevation, the weather is always cooler (even in summer). We always walk a lot in Highlands (we almost never drive because everything so close!), so I pack comfortable shoes and rarely ever wear heels. In the fall and winter, UGG boots are definitely a must! During the daytime, the locals dress casually in jeans, but if you’re headed to a nice restaurant for dinner, you’ll definitely want to dress up a bit more. Pack a dress or nice pants for dinner, and tell your men to pack a button-up shirt! For hiking, I recommend bringing a pair of workout clothes. It’s also nice to go for runs/walks around town in the morning. 🙂

I think that’s it! Let me know if you have any questions about Highlands and I’ll be sure to answer them in the comments!