The 5 Best Places I’ve Traveled in the Fall

Fall might be my FAVORITE season to travel. There’s just something about planning a trip around cooler weather, changing leaves, cozy hotels, good food and spending the day exploring a cute little town that makes me so happy. And over the years, we’ve been lucky enough to visit some truly incredible places during the fall!

Today I’m narrowing it down to five of my absolute favorites. These are all places I’ve personally visited and would go back to in a heartbeat, whether you’re looking for incredible fall foliage, a romantic mountain getaway, a family trip or an excuse to hop on a plane to the English countryside. :)

For each destination, I’m sharing why I love it, where I recommend staying, my favorite restaurants and the things you absolutely HAVE to do while you’re there. So if you’re itching to plan a fall trip this year (or just want to add a few places to your bucket list!), save this one!

I have been to Stowe more times than I can count, it is one of my very favorite towns in Vermont! It’s pretty far north, so if you’re considering visiting Stowe, you’ll want to come here earlier in the fall season (if you wait too long, the leaves will be past peak!). To get there, you will want to fly into the Burlington airport, and from there it is an hour drive to Stowe.

Whenever we visit Stowe, we always stay at the Lodge at Spruce Peak - a GORGEOUS ski lodge with beautiful rooms and even better views. We have stayed both in the hotel rooms and the townhouses, and I love both! With kids, I definitely recommend the townhouse as it is more spacious, with a full kitchen and washer and dryer. The resort has an assortment of restaurants and even a small grocery store, but perhaps the best thing about it is the gondola! The gondola is located right on the property and takes you up Mount Mansfield - at the top is a stunning view of the mountains and the town far below, a gift shop and little stand selling piping hot waffles with real Vermont syrup.

If you’re planning a trip to Stowe, you also have to visit Main Street - with its picturesque white church, coffee shops and touristy shops (including a General Store), you’ll find plenty to do for a few hours. Pick up some real maple syrup and a cute Vermont coffee mug at Stowe Mercantile and then head next door to Bear Pond Books (one of my favorite bookstores!). The roads in Stowe are also beautiful, and you can find a lot of photo spots just through the car window! We particularly loved driving through Smuggler’s Notch State Park.

Carve a few hours in your itinerary to stop by Cold Hollow Cider Mill. You can watch apple cider donuts being made and try some for yourself, as well as shop their extensive Vermont gift store. Be sure to eat lunch at the Luncheonette, the little building right across from the cider mill that offers hard cider (and hard cider tastings!), and a variety of salads, wraps and sandwiches.

Another place you can’t miss is Von Trapp Bierhall and Brewery. Remember the Sound of Music? When the von Trapp family escaped Austria in the 1940s they actually settled in Stowe! The family built a beautiful lodge with sweeping mountain vistas and opened it up to guests in 1950. Today, the Trapp Family Lodge has expanded to include a brewery and you simply MUST stop in for some fresh lager beers and authentic Austrian food!

One of my favorite fall destinations is in my home state, North Carolina! Highlands is a small town in the North Carolina mountains but is quite a luxury destination, with world-class restaurants, hotels and spas. There’s some really good hiking trails and waterfalls to visit, a beautiful downtown area with high-end shops, and some of my favorite restaurants in the world!

My favorite place to stay in Highlands is Old Edwards Inn - 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! If you’re traveling with your furry friend, I recommend Park on Main - an entire hotel centered around dogs, and if you’re traveling with kids, there are many cabin rentals in the area. We also love Old Edwards’ sister hotel Half-Mile Farm, an adults-only retreat near Highlands with chef-made breakfasts and serene mountain views.

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 on a patio, people travel here from all over just to soak up the fresh mountain air and the slow lifestyle. The highlight is definitely the Spa at Old Edwards - rated Condé Nast’s Top Hotel Spa in North America, the Spa at Old Edwards is my favorite spa I’ve ever been to (and I’ve been to a lot of spas all over the world!). All of their skin treatments and massages use herbs and botanicals from their own gardens and are BEYOND magical. I would plan to spend the day at the spa - after your treatment, you can relax in the solarium and listen to the sounds of nature, grab a bite to eat or a glass of champagne in the spa cafe, soak in the jacuzzi tub, or take a shower using their luxurious bath products.

One of my favorite restaurants in the entire world is also located in Highlands: Ristorante Paoletti! It feels like an authentic Italian experience right in the North Carolina mountains, from their handmade pasta to their extensive wine selection. For groceries or a quick bite to eat, I highly recommend stopping by Mountain Fresh Grocery - 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. We also love Buck’s Coffee, Pizza Place of Highlands, Wild Thyme, Madison’s and Bistro on Main.

I know that Vermont is on this list twice, but Woodstock offers a completely different vibe from Stowe, so I had to include it on this list!

Our favorite Airbnb we’ve EVER rented happens to be in Woodstock. This one! It’s one of the prettiest houses we’ve ever stayed in, with a gorgeous and spacious kitchen, beautiful decor, it’s own private pond, and foliage views out of every window. If you’d rather stay in town, I recommend the Woodstock Inn and Resort. It’s walking distance to all of the downtown shops and restaurants, and the front lawn is gorgeous, with lots of green space for kids to run around and play. Speaking of downtown, Woodstock has an INCREDIBLE downtown scene with lots of good shopping, bookstores, coffee shops, and restaurants.

I love Woodstock because most of the restaurants place a huge emphasis on eating local and organic foods. I could spend hours in the Woodstock Farmers Market - it’s a grocery store with local Vermont foods, fresh baked goods (and cider!) as well as fresh meats and cheeses. Our favorite dinner experience is visiting Cloudland Farm - a diversified working farm that offers a true farm-to-table dining experience a few nights per week. The chef uses the most local and seasonal ingredients available. It’s also located in a beautiful setting, in the pastoral hills of Pomfret, Vermont!

While you’re visiting Woodstock, you’ll definitely want to plan a visit to Sugarbush Farm for a maple syrup tasting! You can make a whole day out of it - this 500 acre farm is located on a scenic road just outside of Woodstock. You’ll find free samples of cheese and maple syrup, as well as a farm store full of local jams, mustards, spreads and meats. There’s enough to make a whole little picnic lunch, which you can enjoy on the picnic tables right outside.

My final recommendation for Woodstock (especially if you have kids!) is to visit Billings Farm. This farm is regarded as one of the finest outdoor history museums in country, combining a fully-operating Jersey dairy farm with educational exhibits and interactive programs. My girls loved getting to learn about and pet the Jersey cows, as well as the sheep, goats and pigs!

I feel like a lot of people forget about Colorado during the fall, but it is absolutely GORGEOUS! All of those famous Aspen trees turn the most vibrant shade of yellow, and when the mountains are covered in them, it is truly one of the most beautiful sights. Fall foliage in Aspen typically peaks around the third or fourth week of September, so if you’re planning a trip specifically for the leaves, you’ll want to time your visit accordingly.

One of the best things about Aspen is that you can fly directly into the Aspen airport, which makes getting here surprisingly easy. I highly recommend staying at Hotel Jerome - an Aspen classic! It’s been around since the 1800s and has that old-school, luxurious mountain-lodge feeling that makes you feel like you’ve stepped into another era.

Aspen also has a completely different feel from the New England destinations on this list. Instead of covered bridges and white churches, you get a very Western mountain-town vibe - think cowboy boots, ranches, mountains - but make it luxury! Aspen has some seriously good shopping, including designer stores like Chanel and Louis Vuitton, but I also love wandering into the more Western-inspired shops. You have to stop at Kemo Sabe and get yourself a genuine cowboy hat. It’s such a fun Aspen experience, and you’ll see people wearing their hats all over town!

The restaurants in Aspen are also fabulous. We love Betula, which serves Asian-inspired food with a French twist, and there are so many other great restaurants packed into the downtown area that you really can’t go wrong.

If you only do one thing while you’re there, visit Maroon Bells! The Maroon Bells are two dramatic mountain peaks that rise more than 14,000 feet above Maroon Lake, and the combination of the mountains, the lake and the golden Aspen trees in the fall is absolutely unreal. It looks like a painting. September is an especially magical time to visit because the Aspen trees surrounding the lake turn brilliant gold. You can simply take in the views around Maroon Lake, or make a little adventure out of it and explore one of the hiking trails in the area.

We visited the Cotswolds last year and, although it’s definitely a little harder to get to than the other destinations on this list, it is completely worth it. It was UNREAL. If you’ve ever dreamed of spending a few days wandering through tiny English villages, staying in cozy stone cottages and drinking tea in front of a fireplace, this is the place for you!

The Cotswolds is actually a pretty large area, so there is a LOT to explore. We stayed in a beautiful Airbnb for half of our trip and then spent the other half at The Manor House in Castle Combe, a gorgeous historic hotel. Because the Cotswolds is so spread out, we would sometimes drive 30 minutes to an hour between towns to explore somewhere new, which I actually loved. There are so many beautiful rentals, inns and hotels throughout the area that you really can’t go wrong with where you stay.

There are SO many things to do here, but here are a few of my favorites. First, you have to visit Daylesford Farm Shop. It’s an organic farm shop with fresh produce, beautiful local goods and an amazing farm-to-table restaurant. I could have spent hours wandering around picking up things for our kitchen and looking at all of the gorgeous food and home goods! For a truly quintessential English experience, make reservations for afternoon tea at Slaughters Manor House. This was probably my favorite afternoon tea I’ve ever had! There is something about sitting in a beautiful English manor, drinking tea and eating little sandwiches and pastries that makes you feel like you’ve been transported into a Nancy Meyers movie.

Another place that absolutely blew me away was Restoration Hardware at Aynhoe Park. Yes, Restoration Hardware! It is located inside a stunning historic estate, and it is honestly an EXPERIENCE. People literally go there just to hang out and have lunch because the space is so beautiful. You can also shop for furniture and home decor, but even if you’re not in the market for a new dining table, it is worth visiting just to see the property.

You also have to visit Bourton-on-the-Water, one of the most famous villages in the Cotswolds. The town is built around the River Windrush, which runs right through the center of town, with little stone bridges crossing over the water. It’s often called the “Venice of the Cotswolds,” and it’s easy to see why! There are adorable shops, tea rooms, restaurants and beautiful little stone buildings lining the river. It can get busy, but don’t let that deter you - it’s one of those places that is popular for a reason.

Perhaps my favorite part of our entire Cotswolds trip was something we did with our girls: a fairy walk in Castle Combe! We ordered little picnic lunches and took them on a specific trail through the forest where we searched for tiny fairy doors hidden along the way. When we found one, the girls got to write a note to the fairies and leave it for them inside the fairy house. They were absolutely enchanted by it, and I think it was their favorite part of the entire trip. Honestly, if you’re traveling with kids, I would plan your trip around this!

The fall foliage in England wasn’t quite as brilliant as what you’ll find in New England, so if your number one priority is seeing spectacular red and orange leaves, I’d choose Vermont. BUT... the architecture in England more than makes up for it. The Cotswolds in the fall is all cozy stone cottages, winding country roads, ancient churches, fireplaces, afternoon tea and little villages that look like they came straight out of a storybook. The honey-colored cottages covered in ivy and surrounded by English gardens are unlike anything you’ll find anywhere else.

It’s definitely the most ambitious trip on this list, but if you’re willing to make the journey, I truly can’t recommend it enough. The Cotswolds might just be my favorite fall destination of them all!

Writing this officially has me so excited for one of our fall trips coming up in a few weeks! Every place on this list is so different, which makes it almost impossible for me to pick a favorite. If you want classic fall foliage and small-town charm, I’d head straight to Vermont. Highlands is perfect for a cozy mountain weekend, Aspen gives you the most gorgeous golden leaves with a Western twist, and the Cotswolds is basically my fall Nancy Meyers dream come to life.

Comment below if you have a favorite fall destination that I need to go to!