This year September 23 marked the official first day of our FAVORITE season. FALL.

Yes!!! Bring out your scarves and hats, cute outerwear and boots! Everyone looks food in fall/winter wear! And lets line up for our warm beverages! I am not a Pumpkin Spice Lover (I know, I know , Im craaazzyy, but I hope we can still be friends) , I prefer a black white hot chocolate or a hot mint chocolate (does that redeem me a little?). There is just an amazing feeling inside knowing that we are about to have a change of season and all THE BEST holidays are right around the corner.

But wait… the Weather forecast here in sunny Los Angeles showed 87 degrees! Ugh. There go my cute fall outfits, and I guess I’ll go back to my iced coffee. My shoulders are slumped and the warm glow and fuzzy feeling have turned into genuine warmth aka sweat. Bleh

It’s not just Los Angeles, Houston had a forecast of 87 and was in the high 80’s the entire first week!

We have GOT to get out of these melting pots! Its fall dammit, and I want to wear some boots! (Imagine me stomping my un-booted foot)

Don’t worry y’all, we got you covered. Fall is not a lost cause for us. Breath in. Breath out… if Fall won’t come to us, we will go to Fall! A perfect chance to explore cities and see some absolutely stunning colors that only nature can show.

Here are our 4 favorite cities everyone should visit if they want to experience and enjoy Fall within the US!

1. New York - Fall for the Chic

New York will ALWAYS be on my list for Fall/ Autumn… hellooo there is a movie literally named Autumn in New York (aka the movie where I fell in love with Richard Gere). If movie titles don’t sell the idea, maybe the beautiful views of Central Park or the thermostat forecast in the mid 70’s – low 60’s will. If you are not shy of layering, October is great time to take a bite out of the big apple. This is a great option if you want to see fall but still be in a city.

Year round New York sees over 50 million tourists so safe to say, they know how to keep people busy. I cannot express how much I love the energy of this city, it has its own pace and its own vibe. Yes, it’s a love-it or hate-it city, but everyone should absolutely experience it at least ONCE. Trust me New York in the fall…. Sigh… sorry I was looking into booking a flight out there just thinking about it.

It’s a city to see on foot, with its own unique energy and I would MUCH rather explore and enjoy it while the weather and surroundings are cool but not freezing.

new york1_edited
new york_edited

Some Ways to Enjoy New York’s Fall Weather include:

  • Taking a stroll on the High Line Park (Or enjoy an evening stroll and watch the sunset over the Hudson)
  • Strolling through Central Park and looking at the stunning colors around the trees
  • Getting some MUCH-needed Retail Therapy
  • Walking around the city and just enjoying the crisp weather
  • Outdoor Movie Nights under the stars
  • Get a dose of culture at the world-famous Museums
  • Play outdoor lawn games- you will often see locals in neighborhoods meeting up to play an intense game of Bocce

Not to mention the delicious warm mixed nuts you can enjoy from carts… ohh the smell of sugar melting. and a slice of pizza… good all year round but even better when it’s chilly out and the slice is hot. I am now drooling.

Ideal Travel for Fall Feels: Late September to late October

Travel Notes:

There is usually a 6-7 day forecast of rain throughout the Fall months. Check before you book your flights and accommodations. Cause, getting rain when you want to walk around and aren’t prepared for it? Sucks. If it does rain don’t make your Chanel Mascara run, hop into the MET or Guggenheim. Or drop into one of the fabulous hotels and have a luxurious, beautiful Hi-Tea.

2. Boston, Massachusetts - Fall for the History And Culture Buff

There are only a handful of cities with more historical significance than Boston. With the amazing museums and historical landmarks, Boston is a great getaway for someone who finds their Zen in museums and is hungry for some history.

With all the historical homes and beautiful parks, Boston is a city to bask and enjoy when the trees are changing colors and the weather is just on this side of cold.

You can visit some historical graveyards-not my thing personally but hey, to each their own. Just do me a favor? Please don’t tell me any ghost stories. Please.

Let’s not forget the Amazing food. We will TRAVEL for good food and safe to say the East Coast reigns supreme when it comes to seafood. We would gladly sacrifice my healthy lifestyle (I’m snorting and giggling) for a hot plate of good lobster ravioli. Ok let’s be real, we would ditch our diet for a plate of good food anytime. There is something extra satisfying when it comes to eating in the winter and Boston is a Mecca of culinarily delights.

boston1

Travel Notes:

To experience Fall at its finest, take the trip to Boston from August to September. You will be able to see all the natural colors and stunning beauty the city has to offer. Please note, this is a popular destination for fall lovers (we know why of, course) so be prepared for some higher prices and crowds.

3. Gatlinburg, Tennessee - Fall for the Nature Lover

Gatlinburg-Tennessee-

You can actually still see the first cabin EVER built in the town- built in early 1800’s, talk about surviving the test of time.

Not into history or hiking? No worries, if adventure in the Fall is what’s taking you to this town, you’re in luck. Along with hikes and trails, you can also

  • Zipline
  • Go Rafting in the Pigeon River
  • Play Hillbilly Golf– no, I’m not being bougie it’s really called Hillbilly Golf: An 18-hole miniature golf experience where you are riding in a caged enclosure to get from one golf hole to another. Its real I promise. I’ll even attach a picture. Cause pictures don’t lie. Right?

Enjoy Fly Fishing

If we wouldn’t have identified Tennessee as the home state, the name suggests a quaint town somewhere in Europe, right? The beautiful city has made our list for a variety of reasons.

It may be a lesser known city to the masses, being overshadowed by its other sisters Memphis and Nashville (siblings, what are you going to do? Can get rid of ‘em right?), but Gatlinburg is a small resort like mountain village located in the Eastern part of Tennessee.

Informally known as the gateway to the gorgeous 520,000 acre Great Smokey Mountain Nation Park, this city is perfect for you if you’re up for a hike. Or 2 maybe 3?

There are trails that reward you stunning views and beautiful waterfalls on the way.

1Gatlinburg, Tennessee

Travel Notes:

To experience Fall at its finest in this beautiful city, October is the month you want to visit. It is however, a popular vacation destination so be prepared for peak season rushes (and higher prices). September and November are better in terms of crowds but may be colder therefore you may be limited to certain activities.

4. Portland, Oregon- Fall for the Foodie

portland

From food carts to fine dining you can find everything from hand-pulled noodles and dumplings at the famous cart Stretch the Noodle to some of THE BEST South Asian cuisine in the nation (Try Hat Yai)

Portland has everything a true blue foodie could possibly dream of. Brunch is a serious enterprise, not to be taken lightly. Heated arguments have occurred while debating the best place for brunchers.

So no matter what your pallet is craving sweet, savory, light bite, big bite Portland is a great place to see fall and feel full.

Ohhh Portland, with its stunning, untouched natural landscape, you shouldn’t be surprised that Portland has made the list. What may however surprise you, is that Portland made the cut for its fabulous food options. Yes friends, you read correctly, food.

Our way of thinking is, you get the best of both worlds, unsullied landscapes to look at while you enjoy delicious cuisines, made possible by using ingredients from said unsullied lands. Besides Voodoo Doughnuts (Yup, they are a product of Portland), there is a plethora of options to satisfy even the most discerning food pallet.

Like the big words? Food does that to me. Just feed me and I become super eloquent. Or buy me Chanel. I digress, back to food options.

portland1

Travel Notes:

Thanks to Edward Cullen and Christian Grey, the vast majority of people are aware that there is an overcast in the city (great for vampires) most of the year. October is usually a good time to experience the city, with sunny day’s that are cool but not freezing. There is rain usually 9 days in the month of October and that goes up to 15 days in November.

Final Thoughts

Like This Post? Don't Forget to PIN It!

With summer in full swing and months of being indoor and socially distant, it’s only normal for the travel itch to set in. Unfortunately, we are going through a global pandemic where air travel is super limited. So, what do you do? How do we scratch this itch? We resort to the original form of
Continue Reading

47 Comments

  1. flyeatandrepeat Reply

    WE hope you enjoy reading this post as much as we loved picking our favorite cities

  2. Awesome post. Thanks for also including what to do to enjoy these places in the fall. I will just like to add Long Beach, California to this list.

    • flyeatandrepeat Reply

      We are glad you enjoyed the post! We are LA locals so we wanted to give cities outside of SoCal but yes, Long beach is beautiful!!

  3. Autumn is my favorite time of year and the best season to travel in my opinion. I always struggle every year by choosing where to go because there are SO many options. I moved to North Carolina this year and will be checking out Gatlinburg next week!

    • flyeatandrepeat Reply

      We agree! Everyone looks cute in outerwear and the weather is crisp but not freezing. We hope you enjoyed Gatlinburg!

    • flyeatandrepeat Reply

      We are jealous! We love the East coast, it’s the winters that are too cold for our desert loving bones. We hope you get a chance to check out theses cities first hand.

  4. This is a great list! I am saving it for the future 🙂 Thanks for sharing.

    • flyeatandrepeat Reply

      We are so glad you found the list useful! We hope you get a chance to experience the cities first hand. 🙂

  5. Fall is a great time to travel and I agree about NYC and Boston, both cities where I have lived. Now I want to go to Gaitlinburg because it looks gorgeous! The national park is probably amazing to visit right now.

    • flyeatandrepeat Reply

      Yass, soo many people get scared of the East coast because of the weather but Fall is the perfect time to see the best of these cities! If you are a nature lover, you will love the views at Gaitlinburg 🙂

  6. I’ve never heard of Gatlinburg before, but it sounds like there are a lot of outdoor activities to do here! I like how you included some alternative things to do in NYC if it rains like hopping into a museum or getting something to eat. The photos of Portland in the fall look incredible – it’s my favourite time of the year so I would love to see that in person.

    • flyeatandrepeat Reply

      Gatlinburng is a fall lovers dream city! Sophie is a NY lover and Fall is the BEST time and yes, you should head to Portland and enjoy all the delicious foods and the weather. 🙂

  7. What great suggestions here for fall travel. Gatlinburg is one of our favorites that we have visited many times!

    • flyeatandrepeat Reply

      We LOVE fall weather, so we felt it was only fair to share some cities where you can really enjoy the weather. We wanted to include cities that may not be known to everyone so we are glad you enjoy Gatlinburg!

  8. I love the fall too. A chance to put those boots back on but not yet freeze to death, lol. Love the colour of the leaves and prefer hot chocolate to pumpkin spice too lol

    • flyeatandrepeat Reply

      yayy!!! Nice slouchy boots and a good hot cocoa for the win!!

  9. I LOVE the fall! I went to New York in the fall and it was magical, I would love to check out the other cities that you have mentioned- they look so beautiful!

    • flyeatandrepeat Reply

      YASS, NYC is transformed during the fall and it really is stunning. You will enjoy Boston as well with its stunning parks 🙂

    • flyeatandrepeat Reply

      The food scene there surprised us as well. There is soo much diversity and all the foods are done soo well! You could go on a food crawl and leave verry happy!!

  10. Count me in for Gatlinburg, Tennessee – I like to spend as much of autumn as possible outside enjoying nature and hiking. Although Portland has to be pretty close for their amazing food (and also access to so many gorgeous trails! 😉

    p.s. I’m not into the pumpkin spice either. Hot chocolate makes the fall better!

    • flyeatandrepeat Reply

      Yassss!!! Another person who is not a pumpkin lover 🙂 You will love Gatlinburg, there is such a cute small town vibe and since you are a nature lover you will really appreciate the outdoors 🙂

  11. Gatlinburg looks like it would be so gorgeous to visit in the fall! Thanks for the inspo 🙂

    • flyeatandrepeat Reply

      Yay, we are glad you liked the post. Galtinburg has pleaseantly surprised a lot of people with its beauty. You should for sure check it out 🙂

  12. Of these, I have been to Boston and New York in fall and loved them both. I live in Colorado and we get stunning fall colors here too when the aspens change to a bright shimmering gold – although the best place to see this is in the mountain towns, not so much Colorado cities.

    • flyeatandrepeat Reply

      Colorado is such a great, versatile city! With the fabulous white winters and fun summers you are in a great place! Since you are getting cold weather, you are always welcome to sunny LA if you want to get away from really cold temps 🙂

  13. Vanessa Shields Reply

    Great list of cities! I used to live in both NYC and Portland and loved the fall especially NYC. I miss those fall days as I’m in San Diego now and fall is elusive this year! Haha. I would love to visit Tennessee in the fall as I haven’t been there yet. It looks beautiful!

    • flyeatandrepeat Reply

      Yess!! We are in LA so we feel your pain! As soon as we hit low 70’s we are in sweaters lol. You will love Galtinburg in the Fall it really is beautiful 🙂

  14. Fall colors are beautifullll! I’m really missing that right now (slightly harder to see as much vibrance in CA 😛 ). I’d love to visit Tennessee in the fall! <3

    • flyeatandrepeat Reply

      Same girl same. We are in LA and we are literally getting days that are hot lol. As soon as our temp drops a little we are in boots and sweaters lol.

  15. I have always wanted to experience fall in the States because of all the gorgeous foliage. I would love to fly to New York, enjoy the city in fall, and then head to Tennessee for spending some time in the beautiful nature changing colors.

    • flyeatandrepeat Reply

      yessss, we really have some stunning cities during fall. This post was just the tip of the iceberg but if you are traveling to the states NYC would be a great option because you would be close to soo many cities that really have stunning fall seasons!

  16. My favorite of these is Boston — I’m definitely a history buff! And the fall leaf colors are amazing. I hope next year to travel to the east coast — maybe Boston! — during the fall.

    • flyeatandrepeat Reply

      We loveee the historical significance of Boston. Sophie is also a sucker for the fabulous Boston accent 🙂 We can’t wait to travel soon too!!

  17. I love visiting Gatlinburg in the fall! It’s just a couple hours from where I live so my friends and I go at least once a year. We love renting the cute cabins in the area and eating all the delicious food!

    • flyeatandrepeat Reply

      It is such a beautiful city, you are soo lucky to have access to such a great place for a weekend getaway. Going with friends or even in a group sounds like a great idea!!

  18. Love this! I’ve been to a few of these, but you’ve given me inspiration to visit the rest!

    • flyeatandrepeat Reply

      Thank you! Even when we were writing this post, we starting getting a bad case of wanderust! We hope to get back out to enjoy some Fall weather!!

  19. October is a great time to wrap up warm and visit some cities in the north. In Europe we often travel on a city break in Italy or Germany or Spain in October. The crowds have usually gone and the light is clear. A great post, thank you.

    • flyeatandrepeat Reply

      We love layers and sweaters! We are fascinated by the Eurpean seasonal travel trends so its nice to know how the locals do it. We were supposed to be in Italy this september (alas Covid) we hope you are staying safe and we are glad you enjoyed the post!

  20. Interesting – I always thought that the best places for Autumn are in New England – with the Indian summer and all that jazz. But since all these places are in the US where I cannot travel right now, anyway, I have to look for a good place here in Europe.
    Actually, I find that the best places in Autumn are in in woods with the color of leaves changing – and when the sun shines through the trees….Golden Fall 🙂

    • flyeatandrepeat Reply

      The US is full of seasonal surprises. We are fortunate to have many many regions that really have beautiful seaonal vibes. We hope you are able to find a place in Europe that gives you a Golden Fall 🙂

  21. Fun post! I love fall vibes. I def agree with NYC and Boston, but I have yet to visit the other two cities! I would also add Burlington, VT (but that’s because I’m from here!)

    • flyeatandrepeat Reply

      We are glad you enjoyed the post! There are sooo many cities we could add and now, we want to visit Burlington!!

  22. The colours of Fall are really mesmerizing and indeed a celebration of nature. The places you have listed seem to vie with each other to showcase the enchanting colours of Fall. New York, Boston, Tennesse, all look radiant.

Write A Comment